Sugar daddy sites have risen in popularity over the last several years as society becomes more comfortable with unconventional relationships. As more and more people seek either companionship or financial security, sugar arrangements have become very attractive.

Unfortunately, the popularity of sugar relationships has caused an influx of sugaring sites to pop up. Some sites do their part in vetting the members, but others invite scammers, leeches, flakes, and fakes.

We’ve done the leg work for you and have found the best sugar daddy sites where a sugar daddy can meet a sugar baby and vice versa. These sites strike the delicate balance between safety and fun. We review what’s best about a site for daddies and what’s best for babies.

These are our brand new rankings for 2022.

The Best Sugar Daddy Sites and Apps in 2022

RankSiteBest For1.SugarDaddy.comOne of the oldest and more reliable sites2.Seeking ArrangementBest reputation3.Secret BenefitsBest mix of daddies and babies4.SugarDaddyMeetVerified income feature5.SugarDaddyForMeQuickest way to find an arrangement6.Ashley MadisonJudgement free sugar dating site7.What’s Your PriceBest for women to set their own price8.Sugar SearchBest database of local sugar daddies9.R/SugarBabyFree way to find sugar babies10.Elite SinglesMeet intellectual sugar babies and daddies11.Established MenBest for daddies seeking a long term arrangement12.RichMeetBeautifulMost secure and discreet site13.Miss TravelBest for sugar babies who like to travel14.Wealthy MenMost straightforward sugar dating site15.AgeMatchFind younger women16.SudyBest sugar dating app17.SugarBookBest sugar app for babies

1. SugarDaddy.com – Best overall site

Sugardaddy.com is one of the most reliable sugar daddy sites around and has been around for quite some time. The site is hailed as one of the greats because it verifies all of its members (daddies and babies) and there are almost 10 million members and counting. At any given time, the site is active with several thousands of users and nearly 2/3rds are babies looking for someone to take care of them.

Free members can actually enjoy tons of features (like sending kisses, using the advanced search feature, and responding to paying members), but a membership is well worth it and pretty affordable compared to its competitors. It’s a credit-based system and costs around a quarter per credit. Privacy is a top priority on Sugardaddy.com, making it easy to discreetly enter into relationships.

What it’s like for daddies:

70% of the users on sugardaddy.com are babies looking to be spoiled. With millions of users, this makes being a daddy on the site extremely easy and entertaining. Credits can be used to get in touch with the babies and they won’t cost you much. Because privacy is taken so seriously on this website, there’s no need to fear your identity being revealed. Furthermore, daddies can rest easy knowing they won’t be scammed by any members given that they are all verified.

What it’s like for babies:

Sugar babies tend to love the ease of this site and how slick it is. Other sugar baby sites tend to look shady or seedy, but sugardaddy.com is slick and modern. It makes it easy to layout exactly what you’re looking for in a daddy. One drawback is the fact that most of the users are babies, so there’s some stiff competition out there. But with millions of daddies online searching, finding the right one shouldn’t be too difficult.

2.  Seeking Arrangement – Most popular sugar daddy app

Seeking Arrangement is the largest, most successful, and most referenced sugar daddy site available. There’s a large possibility that you’ve heard of it. If you aren’t already signed up and are wondering if it works, the answer is yes. Seeking Arrangement boasts over 10 million users in over 130 countries. The website itself is very discreet and the Seeking team works tirelessly to protect its members from anything that might jeopardize physical or financial safety. Read our full review here.

What it’s like for daddies:

Seeking has one of the best female-to-male ratios for sugar daddies. There’s also an understanding on the site that relationships are no-strings-attached, and women are both very sexual and extremely beautiful. Maintain anonymity by putting revealing photos or face pictures into private galleries that you grant access to. This is not a free sugar daddy site for the daddies, but it is for the babies.

What it’s like for babies:

Seeking Arrangement makes it easy for young women to sign up. There’s a way to check out each daddy’s net worth, so you can be better informed of what type of arrangement they’d be able to handle. The site is also 100 percent free for babies!

3.  Secret Benefits – Best gender ratio

SecretBenefits.com is one of the most popular and stylish sugar daddy dating websites. It has a modern and fresh look along with an easy-to-use interface which has encouraged millions of attractive and wealthy individuals to join and search for a positive sugar dating experience on the site. Due to its popularity and stellar reputation among the site’s members, there is a constant flow of new hopeful sugar daddies and sugar babies as well as a very active member base.

Anyone can signup, create a profile, and search for free. Sugar babies can enjoy the site and its features for free. If a sugar daddy finds a sugar baby of interest, they need to purchase credits to open a chat with them. There should be no lack of potential candidates among the millions of members as the gender ratio is about 50/50.

What it’s like for daddies:

Signing up as a sugar daddy is very fast and painless. You can also choose to start a very basic profile to search for potential sugar babies in your area before committing too much time or money. Another great feature if you’re looking for a discreet relationship is you can hide your profile at any time as well as go invisible for 24 hours and browse profiles in secret. These features help maintain your privacy while discreetly allowing you to find your perfect sugar baby.

What it’s like for babies:

Sugar babies love using Secret Benefits not only because it’s free, but also because the site’s outstanding support team keeps the riffraff out which provides a safe platform full of serious and active sugar daddies that are not looking to waste anyone’s time. Getting your profile verified via a short intro video also encourages daddies to reach out once they see that you are the real deal. The success rates for legit, happy, and ongoing sugar daddy relationships are extremely high on SecretBenefits.com, so it’s really just about getting signed up and putting yourself out there to find exactly the type of daddy you’re looking for.

4.  SugarDaddyMeet – For rich men who can spoil

SugarDaddyMeet, one of the original sugar dating sites, doesn’t sugarcoat its true intentions. According to the site, it’s only available to men who live in the 20 richest countries in the world. By attracting affluent men, it also attracts beautiful young women. Verifying income and wealth are two major features on SugarDaddyMeet, making it one of the best sugar dating sites for the ladies.

What it’s like for daddies:

For one, you’ll need to actually be rich to get approved for SugarDaddyMeet. Those who meet the requirements are introduced to a world of beautiful females. The platform itself feels like other social media sites that you may already be familiar with. It’s very casual and generally a breeze finding a mutually beneficial arrangement.

What it’s like for the babies:

This site has plenty of features that make women feel safe using it. You can verify income and let the site know what you’re looking for in a sugar daddy. Using a handy algorithm, it’ll match you up based on your preferences. A free membership is all you’ll need!

5.  SugarDaddyForMe – Speedy matching process

This chic site is slick in design and even better in matching capabilities. It doesn’t hide the fact that it’s a tried and true sugar daddy site designed for arrangements. This is made clear for both the women and the men who join SugarDaddyForMe.

What it’s like for daddies:

You should know first that the payment structure is unique. The membership tiers are based on how much time you want to buy rather than what you have access to. SugarDaddyForMe will want to verify your income, but there’s not much to it after that. You’re essentially brought into the SugarDaddyForMe world within minutes, making this platform one of the fastest ways to find a date.

What it’s like for babies:

This is a free sugar daddy site for you! Signing up takes only minutes and you’ll be glad to know that SugarDaddyForMe will want to know what your ideal arrangement would be. This can all be altered later if you change your mind.

6.  Ashley Madison – Find a casual companion

Ashley Madison is the site that people hate admitting they love. Sure, it’s received some shady press over the years, but it works marvelously. Though linked to affairs, it’s a perfect site for those in open-relationships to find fun arrangements with other folks. It’s a completely open-minded and judgment-free space for people to explore sensual relationships.

What it’s like for daddies:

Ashley Madison can be used as a sugar site. It follows a credit-based payment structure that allows men to communicate with women. There’s nothing on Ashley Madison to weed out the sugar babies from the rest of them, so you’ll need to use the age preference feature to find the ladies and chat to see if they are interested. Women are free to join, making it a great breeding ground for relationships with younger college-age women.

What it’s like for babies:

Men on Ashley Madison are usually looking for excitement, and sugar babies know how to have fun. There are a lot of wealthy men looking for younger women on the site, so if you specify that you are looking to set up an arrangement, you’ll have no problem finding a handsome catch.

Want even more about Ashley Madison? Check out our full review.

7.  What’s Your Price – Bid on dates

On many sugar sites, the idea of an arrangement is implied but not always enforced. In other words, SDs don’t feel like spending or SBs ask for too much. On What’s Your Price, the intention is clear. It’s about an agreement or arrangement that works for both parties. What’s Your Price will set everyone up with their ideal situation so that the minutiae of finances don’t cloud the fun! And it was created by the established folks behind Seeking, so you know it’s legit.

What it’s like for daddies:

You will feel like you are shopping for gorgeous women through an online marketplace. We hate to boil it down to an online shopping experience, but that’s kind of how it works! You will be shown tons of ladies who have a price in mind. Then, you can bid on anyone you find attractive or worth your time. You can also send virtual gifts and make bids as low as $10. You don’t have to be “wealthy” to join.

What it’s like for the babies:

What’s Your Price puts you in total control, which is a nice alternative to the chaotic free-for-all approach that other sites have. The only negative to What’s Your Price is that there is a lot of competition. There are 3 million members and counting, which means that your ad is going to have to be competitive.

8.  Sugar Search – Check out “Members Currently Online” before chatting to avoid flakes

It’s just as it sounds. Sugar Search is an easy to use search engine to find a local sugar daddy.

Sugar Search only operates in a few cities. Sorry babies and daddies, if you’re not in NYC, Chicago, Los Angeles, Houston, Phoenix, San Antonio, or Philadelphia, this isn’t the site for you.

Sugar Search goes to admirable lengths to ensure all the accounts are legit. Some slip through the cracks, but the moderation team is pretty on top of it.

Best of all, the site has great customer service and makes it easy to cancel a membership if you’re over it.

What it’s like for daddies:

It’s a super simple sign up process for daddies. Fill in a few fields, verify some personal info, and you’re set. Sugar Search has a great daddy to baby ratio, so it shouldn’t be too hard to meet a baby. The chat feature is slick and easy to use. If you want your profile to appear toward the top of search results, opt for the Diamond Membership. It really does increase the amount and quality of matches.

What it’s like for the babies:

Babies, you won’t be disappointed. Sugar Search is the ultimate sugar daddy search tool if you’re in one of their cities. Sugar Search requires daddies to verify their personal information, so you won’t encounter too many fraudulent accounts. Do your own due diligence by chatting with a prospective daddy first. The sheer volume of options means you’ll likely connect with someone shortly after you sign up.

9.  Reddit (r/SugarBaby) – Top sugar forum

Reddit is a site that gets a ton of volume. As a general forum for a huge range of topics, people come to Reddit to get information about virtually anything you can think of. It works for sugaring, too, on the subreddits that are related to the subject. If you don’t already know, a subreddit is a specific message board. For the best sugar daddy action, visit the /r/SugarBaby board. We should also warn you that sexy photos flood the page!

What it’s like for daddies:

This subreddit has over 80K users, making it more intimate than most but still giving you a ton of options. The best part is that it’s one of the only free sugar daddy sites on this list. Men aren’t allowed to post, but you can browse through the photos and proposals of the women on the page.

What it’s like for the babies:

You can post on this forum photos and a description of your ideal relationship. If a guy sees you on the page and is interested in pursuing you, he will direct message you through the platform! To post, you will need to go through a verification process, but it’s not complicated.

10.  Elite Singles – Dating site for educated daddies and babies

Elite Singles was not designed specifically for sugaring. It’s a premium dating site that caters toward educated and successful individuals looking for someone who is like-minded. As a baby, you should be seeking something serious when you join Elite Singles. This site is made for real relationships, not a one-time hookup. A majority of the people on this site are college-educated, regardless of age, so that’s another thing to keep in mind.

What it’s like for daddies:

Elite Singles is ideal for the man (or woman) who is interested in meeting an intelligent, independent person to shower with affection or anything else. One of the best things about Elite Singles is that nobody is flakey. People are genuinely searching for their other half and they aren’t greedy for cash because they are successful themselves.

What it’s like for the babies:

This is an app best suited for the baby who isn’t just in this for the money. You don’t need to be wildly successful to get on Elite Singles, but you should have a semblance of independence and perhaps a college degree (or working towards one). This isn’t the quickest way to find a sugar daddy, but it is a place where you’ll meet successful people.

11.  Established Men – Great for long-term sugar dating

If you couldn’t gather from the name, Established Men is a dating site created for successful men looking for a relationship. Men who are established and wealthy often don’t find much time to date around. This site makes finding a partner very simple. It’s not a hookup site but rather a place that caters directly to wealthy guys who want a relationship. Though not exclusively for sugar relationships, women aren’t charged for a membership, making it feel like a free sugar daddy site for them.

What it’s like for daddies:

Established Men is not a free sugar dating site for men, but that shouldn’t be a problem if you are, in fact, established. Through the platform, you are able to send gifts and interact with the beautiful ladies that this website attracts. There are new members daily, so you’ll never run out of options!

What it’s like for babies:

Step into the world of Established Men. These are individuals who know their worth, so they might be tough to please. What’s nice about the site is that these guys aren’t expecting you to come to them with a set arrangement. They just want to spoil someone special with bags, shoes, and more.

12.  RichMeetBeautiful – Encrypted sugar daddy site

Contrary to popular belief, RichMeetBeautiful is not just for rich men. Anyone who is reasonably well off can still engage with beautiful men and women through the platform. It’s also one of the most secure sugar dating sites because it uses encryption security.

What it’s like for daddies:

RichMeetBeautiful claims to be rich in several ways: experience, romance, passion, style, and so on. It also explicitly says “no sugar dating” on the homepage. You’re probably asking yourself why it even made the list. It’s a site for successful individuals to meet one another through a scientific matchmaking algorithm. If you want to find a younger woman to spoil, you will absolutely be able to.

What it’s like for babies:

RichMeetsBeautiful is not explicitly for sugar dating. It is a site where you can converse with men who enjoy spoiling their significant others. It’s built for long-lasting relationships, so be prepared to meet people who want to find real love.

13.  Miss Travel – Best for the adventurous

Miss Travel puts an exciting spin on sugar dating. Rather than finding a companion locally, this site encourages people to find partners from places they’d love to travel to! It adds a whole new element to the fun of sugar dating, and women can join this site for free.

What it’s like for daddies:

SDs in open relationships or looking for fun outside of a relationship love to use this site while they travel for business. However, it’s also convenient for men who want foreign women to come to them. There are a ton of beautiful women who use Miss Travel because they are looking for an adventure with a well-to-do man.

What it’s like for babies:

Ever wanted to travel the world? This is one of the best ways to make that happen. The daddy you find will likely pay for the entire trip. There’s also an exciting “Create a Trip” feature that allows you to plan a wonderful vacation right there on the site.

14.  Wealthy Men – A no-frills approach to sugaring

Wealthy Men is the most straightforward sugar daddy website available to users, and it’s very reliable too. It promises young women that they will meet the wealthy man of their dreams. And, it has a guarantee for its paid members that they’ll find someone in three months. Members can rest assured that Wealthy Men will absolutely work for them.

What it’s like for daddies:

We’ll be honest: Wealthy Men does not make it that easy on the guys initially. You will have to prove that you make at least 85K by providing documentation stating so and comment on how much you’re willing to spend on a baby. While this is annoying, it maintains the integrity of the site.

What it’s like for babies:

This is one of the best sugar daddy sites out there. The financial aspect works in your favor. But you’ll want to pay for it, as the free version doesn’t allow for messaging.

15.  AgeMatch – Best for relationships with significant age gaps

AgeMatch doesn’t market itself as a sugar website. Instead of sugar daddies and young models, it pins itself as a dating platform for people with a very large age gap between them. This works for arrangements because most of the companionships on this site are between successful older men and stunning younger women.

What it’s like for daddies:

Some men don’t want arrangements and prefer the idea of spoiling someone who enjoys their company. For those types, AgeMatch is perfect. You will feel like you are on a real dating site and not a shady or seedy arrangement site, which is a nice alternative to the normal setup.

What it’s like for babies:

The expected age gap works in your favor, but the fact that sugaring is more implied than explicit does not. You won’t be asked about your preferred arrangement. However, there are plenty of wonderful successful older men at your disposal and you are welcome to present them with your terms.

16.  Sudy – A sugaring mobile app

Sudy is a fantastic app in terms of usability. It functions really well and is set up in such a way that makes it easy to meet someone new. There are some things about Sudy that aren’t perfect, which is why it’s at the bottom of our list, but it’s certainly a great option for someone who would rather use their phone than a desktop to find a date.

What it’s like for the daddies:

To join, you’ll need to make over 200K. Once you verify this, you will be introduced to the world of beautiful ladies (there’s a 4:1 male to female ratio). Gorgeous women like to know that you make enough to entertain them, so the verification works in your favor. Sources report having trouble deleting their profiles though, so that might be a turn-off for you.

What it’s like for babies:

There are more women than men, which means it’s competitive. But at the same time, Sudy is also very safe. The Sudy staff work tirelessly to moderate the platform and remove suspicious or fake profiles.

17.  SugarBook – Great for alternative arrangements

Sometimes arrangements aren’t all money-based. There are ambitious women (or guys) out there who desire connections, advice, opportunities, and financial help. Sources say that SugarBook is ideal for that type of relationship with a sugar mama or sugar daddy because each interaction begins by laying out expectations for one another.

What it’s like for daddies:

You will need to verify your income before getting accepted to SugarBook. This is technically a free sugar daddy site for men, but the premium option will show you many more profiles. We’ll admit that it’s limited on the free side.

What it’s like for babies:

You can join for free or pay for more features, that’s totally up to you. Try the free version first, though, because the features just include access to more daddies and a more specific search. You might find what you’re looking for on the free version alone. You’ll have a chance to create a profile where you can explain what you’re interested in.

Have Questions About Sugar Daddies and Babies? Here Are Some FAQs

What Does a Sugar Daddy Do?

A sugar daddy’s role is relatively simple. His “job” consists essentially in using his wealth to spoil the sugar baby. This might include fancy dinners, high-end alcohol, even vacations all around the world. In return, the sugar daddy expects a certain degree of companionship. 

Where Can I Find a Sugar Baby?

Finding a sugar baby is basically the same process as finding a sugar daddy. You simply need to leverage the sites and apps that exist specifically to unite would-be sugar babies with sugar daddies. One of the best sites for this is Seeking, though there are many others (the reviews for which you can see in the above article). 

What Does a Sugar Baby Do?

A sugar baby simply provides companionship to a sugar daddy. In exchange for being spoiled and receiving gifts, dinners, vacations, etc., a sugar baby is expected to provide companionship and affection to the sugar daddy. This isn’t necessarily always sexual, as that depends on the sugar daddy and the terms that you establish. It’s a good idea to be upfront about expectations from the get-go to ensure that everything goes smoothly. 

Is It Ok to Have a Sugar Daddy?

Some people may be wondering if it’s morally okay to have a sugar daddy. Well, that depends. Is the sugar daddy married with kids and doing this on the side without anyone knowing? That’s definitely a questionable thing to do morally speaking. But if no one else is at risk of being hurt by the relationship, and everything is consensual, then it’s perfectly okay to have a sugar daddy. 

Are Sugar Daddy Sites Legit?

Sugar daddy sites can definitely be legit. That said, sugar relationships have become more popular and so many sites have popped up lately. Not all of them are legitimate, so it’s important to be careful. A good idea would be to stick with the sites reviewed above, especially the biggest and most well-established ones. 

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For their inaugural production, Violet Sky Theatre company has chosen Tennessee Williams’s Summer and Smoke from 1948.

As is expected with any of Williams’s canonical works, Summer and Smoke is a portrait of the delicious agony of unrequited love. Alma Winemiller, the minister’s daughter, has been in love with John Buchanan, the boy next door, for her entire life. When John returns to their small Mississippi hometown after finishing medical school out east, Alma’s feelings return with the vigor of the Gulf winds that the townspeople pray for during their insufferably hot summers. 

Summer and Smoke
Through 7/31: Thu-Sat 7:30 PM, Sun 3 PM, Reginald Vaughn Theater, 1105 W. Thorndale, violetskytheatre.com, $27

Alma is anxious, and Lindsey Zanatta gracefully and authentically carries that burden in her performance. She is quick-witted but reserved, beholden to the expectations of her religious upbringing and the belief that if she is the perfect lady, love will come. As John, Joshua J. Volkers embodies the swagger of a man who can have anything he wants, and he wants it all—sex, booze, parties, and maybe Alma—right now. Where Alma stutters, John stalks. Together, they invoke collective, trepidatious joy in the moments where their power dynamic flips, when Alma manages to catch John off his guard.

Summer and Smoke is a spiritual, sexual romantic drama, and Kevin Rolfs’s scenic design nails the southern Gothic aesthetic that carries this inherent dichotomy. Where there’s smoke, there’s fire, and in this performance, it’s stoked by the constant friction between Alma’s beliefs and John’s instincts, the heat when they hold hands. 

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Reader senior writer Ben Joravsky riffs on the day’s stories with his celebrated humor, insight, and honesty, and interviews politicians, activists, journalists and other political know-it-alls. Presented by the Chicago Reader, the show is available by 4 p.m. Tuesdays through Fridays at chicagoreader.com/joravsky—or wherever you get your podcasts. Don’t miss Oh, What a Week!–the Friday feature in which Ben & producer Dennis (aka, Dr. D.) review the week’s top stories. Also, bonus interviews drop on Saturdays, Sundays and Mondays. 

Chicago Reader podcasts are recorded on Shure microphones. Learn more at Shure.com.

Chicago Reader senior writer Ben Joravsky discusses the day’s stories with his celebrated humor, insight, and honesty on The Ben Joravsky Show.

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Multi-instrumentalist, producer, and vocalist Sam Thousand moved to Chicago from Texas in 2009, and within a year he’d joined hip-hop fusion outfit Sidewalk Chalk. He’s since become deeply embedded in several overlapping arts communities, gaining increased visibility under his previous stage name, Sam Trump—I first saw him perform solo in 2018, during a cross-genre Steppenwolf show presented by Growing Concerns Poetry Collective. He does work as a hired gun for musicians who want a soulful trumpet player on their recordings, and in 2016 his experience booking shows around town helped him cofound ChiBrations, a live performance series and advocacy group that elevates local soul musicians. Thousand also wrote the score for Unapologetic, a 2020 Kartemquin documentary about Black millennial abolitionists directed by Ashley O’Shay and coproduced by TRiiBE cofounder Morgan Elise Johnson. 

As told to Leor Galil

Through the pandemic, I transitioned to fully performing solo. I started this online show called The Midnight Hour. I was making live beats with my looping station and my synthesizer and playing the ukulele and playing trumpet and singing. I was performing original songs; there’s some covers. It was a great way to interact with the audience and engage with my fans—we needed each other. 

An episode of The Midnight Hour from early 2021

Now that the city’s back open, I want to say June is probably the apex of my business. Leading up to this moment I was doing more performances, but a lot of them remain small. I was like, “Hey, I can just come and perform solo.” I have a lot of different iterations of my performing, so it just works out to be able to have so much variety while I’m stimulating the same market within Chicago. 

I have a duo with this gentleman named Justin Dillard, who plays the Hammond keyboard. We have a standing residency at Pilsen Yards, which is every last Thursday. I also have a trio—we started at Soho House; we were playing there once a month. 

I also have two sextets. One is an acoustic group, Acoustic Audile. Another one is a more dance, funk, soul, and R&B group—it’s called the Soul Vortex, and we’ve been doing a whole lot lately. Prior to the pandemic we recorded a live album—I recently was pushing it a lot. We did a listening party for that album, because I’ve been holding onto it during the pandemic. Once things started opening up, we finished it up, did all the editing and mixing. I actually reached back to everyone who was at the show and invited them back to the Promontory—where we recorded it—to hear it in the space. We mixed the whole album and did a reception and played the album for them. 

I do all my own booking; I do all my managing. I’m getting busy, especially in this last month. I’d been a booking manager for a couple different venues throughout Chicago. For about four and a half to five years now, I’ve been a booking manager for Untitled Supper Club, which is a speakeasy restaurant—it’s in River North. I was playing there—they offered me a residency back in the day, when I was performing. Then there was an opportunity to do some curating, and I was moving toward that space anyway, of just wanting to do more with my platform. 

Curtis Mayfield Tribute with Sam Thousand backed by Verzatile
Wed 7/6, 7:30 PM, Untitled Supper Club, 111 W. Kinzie, reservations recommended, all ages

Sam Thousand & Justin Dillard
Thu 7/28, 7 PM, Pilsen Yards, 1163 W. 18th, reservations recommended, all ages

I’m a founder of an organization called ChiBrations, which is shedding light and bringing more awareness to soul music in Chicago. We’ve got a Jazz Fest, we’ve got a Blues Fest, but prior to us starting ChiBrations there was no Soul Fest. Now there’s the Chi-Soul Fest at Navy Pier, and that kind of happened around the same time. Two years before the pandemic, ChiBrations partnered with the Chi-Soul Fest, and they let us have a block of time in the festival—to actually curate a whole three- to four-hour block of time. 

What ChiBrations was originally, it was bringing in an artist and their band to come into our studio—wherever we had a space. We partnered with the Den Theatre, so they just gave us a room to work out of. We would build it out, and then we would record two songs with them. Every month we would highlight an artist that we recorded; we would put out a video for one week, then wait two weeks and put out another. For that whole month it would be highlighting an artist, promoting these shows they’ve got. This is another way to give back, so I’m always trying to find ways to connect but also use my platform to really lift up others. 

Sam Thousand (then known as Sam Trump) performs at a ChiBrations session in 2019.

Throughout the three years that we did things before the pandemic, we would highlight about eight to ten artists at the end of each year. We would do an anniversary show—which happened usually in November, October—where we would bring all of those artists, and we would put them all onstage for one night. I’d be the one coordinating all these things and curating all the artists and all that. We’re looking to do more with ChiBrations, because ChiBrations needs to expand beyond soul music. 

There’s so much of the underground scene that really gets no love, and a lot of them are people of color. If you look at the festivals—I even tried to get my band at some festivals on the north side. There’s maybe a couple Latin bands, but I personally feel like it should be representing more of what Chicago is and its diversity, and even its political stance. 

I started playing trumpet when I was seven. I was in a magnet school, kind of like a fine arts elementary. My brother started playing the trombone when he was in third grade—he was a year older. Once you get to third grade, you’re able to actually get into an elective program, and so I was inspired by him to get into music. I wanted to play drums, but drums were inundated by the time I was making my choice, so I had to choose another instrument, and the trumpet resonated. It was a wonderful program, very competitive, and kept me busy—kept me out of a lot of trouble. And it kept me challenged. 

I like community; I’m an extrovert. [That school music program] allowed me to be around a lot of people, and taught me how to be a team player, taught me about individuality as well, and responsibility—because you’ve gotta learn your part, but for a bigger picture, right? I think that upbringing really prepared me for a lot of things I do now. I understand, as an individual, I need to make an impact, but there’s also the broader picture to look at, and how I operate within the scene in Chicago. How I operate as a Black male in America. How I operate as a teacher and a mentor. How I operate as a trumpet player, even, or singer. 

I got offered a scholarship to come out here and play in the big band at Columbia College. I did an audition through YouTube, and they accepted me. I came out to Columbia College, was a full-time student, playing trumpet. Although I was a singer and a songwriter, I wasn’t really pushing that in school, I was really just trying to do my job during the day. By night, if I wasn’t working my night job, I was out on the scene, hitting open mikes, just really getting my name out. 

I first made my name as an artist at an open mike—specifically a poetry open mike. The scene is super vibrant—it was back then as well—and I just really started to meld into what was going on in the scene, joining bands. I joined a band called Sidewalk Chalk. We toured for five years in the past, independently. I joined that band literally three months after I came to Chicago.

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Multi-instrumentalist, producer, and vocalist Sam Thousand moved to Chicago from Texas in 2009, and within a year he’d joined hip-hop fusion outfit Sidewalk Chalk. He’s since become deeply embedded in several overlapping arts communities, gaining increased visibility under his previous stage name, Sam Trump—I first saw him perform solo in 2018, during a cross-genre Steppenwolf show presented by Growing Concerns Poetry Collective. He does work as a hired gun for musicians who want a soulful trumpet player on their recordings, and in 2016 his experience booking shows around town helped him cofound ChiBrations, a live performance series and advocacy group that elevates local soul musicians. Thousand also wrote the score for Unapologetic, a 2020 Kartemquin documentary about Black millennial abolitionists directed by Ashley O’Shay and coproduced by TRiiBE cofounder Morgan Elise Johnson. 

As told to Leor Galil

Through the pandemic, I transitioned to fully performing solo. I started this online show called The Midnight Hour. I was making live beats with my looping station and my synthesizer and playing the ukulele and playing trumpet and singing. I was performing original songs; there’s some covers. It was a great way to interact with the audience and engage with my fans—we needed each other. 

An episode of The Midnight Hour from early 2021

Now that the city’s back open, I want to say June is probably the apex of my business. Leading up to this moment I was doing more performances, but a lot of them remain small. I was like, “Hey, I can just come and perform solo.” I have a lot of different iterations of my performing, so it just works out to be able to have so much variety while I’m stimulating the same market within Chicago. 

I have a duo with this gentleman named Justin Dillard, who plays the Hammond keyboard. We have a standing residency at Pilsen Yards, which is every last Thursday. I also have a trio—we started at Soho House; we were playing there once a month. 

I also have two sextets. One is an acoustic group, Acoustic Audile. Another one is a more dance, funk, soul, and R&B group—it’s called the Soul Vortex, and we’ve been doing a whole lot lately. Prior to the pandemic we recorded a live album—I recently was pushing it a lot. We did a listening party for that album, because I’ve been holding onto it during the pandemic. Once things started opening up, we finished it up, did all the editing and mixing. I actually reached back to everyone who was at the show and invited them back to the Promontory—where we recorded it—to hear it in the space. We mixed the whole album and did a reception and played the album for them. 

I do all my own booking; I do all my managing. I’m getting busy, especially in this last month. I’d been a booking manager for a couple different venues throughout Chicago. For about four and a half to five years now, I’ve been a booking manager for Untitled Supper Club, which is a speakeasy restaurant—it’s in River North. I was playing there—they offered me a residency back in the day, when I was performing. Then there was an opportunity to do some curating, and I was moving toward that space anyway, of just wanting to do more with my platform. 

Curtis Mayfield Tribute with Sam Thousand backed by Verzatile
Wed 7/6, 7:30 PM, Untitled Supper Club, 111 W. Kinzie, reservations recommended, all ages

Sam Thousand & Justin Dillard
Thu 7/28, 7 PM, Pilsen Yards, 1163 W. 18th, reservations recommended, all ages

I’m a founder of an organization called ChiBrations, which is shedding light and bringing more awareness to soul music in Chicago. We’ve got a Jazz Fest, we’ve got a Blues Fest, but prior to us starting ChiBrations there was no Soul Fest. Now there’s the Chi-Soul Fest at Navy Pier, and that kind of happened around the same time. Two years before the pandemic, ChiBrations partnered with the Chi-Soul Fest, and they let us have a block of time in the festival—to actually curate a whole three- to four-hour block of time. 

What ChiBrations was originally, it was bringing in an artist and their band to come into our studio—wherever we had a space. We partnered with the Den Theatre, so they just gave us a room to work out of. We would build it out, and then we would record two songs with them. Every month we would highlight an artist that we recorded; we would put out a video for one week, then wait two weeks and put out another. For that whole month it would be highlighting an artist, promoting these shows they’ve got. This is another way to give back, so I’m always trying to find ways to connect but also use my platform to really lift up others. 

Sam Thousand (then known as Sam Trump) performs at a ChiBrations session in 2019.

Throughout the three years that we did things before the pandemic, we would highlight about eight to ten artists at the end of each year. We would do an anniversary show—which happened usually in November, October—where we would bring all of those artists, and we would put them all onstage for one night. I’d be the one coordinating all these things and curating all the artists and all that. We’re looking to do more with ChiBrations, because ChiBrations needs to expand beyond soul music. 

There’s so much of the underground scene that really gets no love, and a lot of them are people of color. If you look at the festivals—I even tried to get my band at some festivals on the north side. There’s maybe a couple Latin bands, but I personally feel like it should be representing more of what Chicago is and its diversity, and even its political stance. 

I started playing trumpet when I was seven. I was in a magnet school, kind of like a fine arts elementary. My brother started playing the trombone when he was in third grade—he was a year older. Once you get to third grade, you’re able to actually get into an elective program, and so I was inspired by him to get into music. I wanted to play drums, but drums were inundated by the time I was making my choice, so I had to choose another instrument, and the trumpet resonated. It was a wonderful program, very competitive, and kept me busy—kept me out of a lot of trouble. And it kept me challenged. 

I like community; I’m an extrovert. [That school music program] allowed me to be around a lot of people, and taught me how to be a team player, taught me about individuality as well, and responsibility—because you’ve gotta learn your part, but for a bigger picture, right? I think that upbringing really prepared me for a lot of things I do now. I understand, as an individual, I need to make an impact, but there’s also the broader picture to look at, and how I operate within the scene in Chicago. How I operate as a Black male in America. How I operate as a teacher and a mentor. How I operate as a trumpet player, even, or singer. 

I got offered a scholarship to come out here and play in the big band at Columbia College. I did an audition through YouTube, and they accepted me. I came out to Columbia College, was a full-time student, playing trumpet. Although I was a singer and a songwriter, I wasn’t really pushing that in school, I was really just trying to do my job during the day. By night, if I wasn’t working my night job, I was out on the scene, hitting open mikes, just really getting my name out. 

I first made my name as an artist at an open mike—specifically a poetry open mike. The scene is super vibrant—it was back then as well—and I just really started to meld into what was going on in the scene, joining bands. I joined a band called Sidewalk Chalk. We toured for five years in the past, independently. I joined that band literally three months after I came to Chicago.

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“When we go to a skate park, we take up space, and then all of a sudden you don’t see a bunch of guys trying to tell you to move out the way, ’cause we’re the majority now,” says Lid Madrid. “And we’re taking up space, and just changing the way that skate parks traditionally look. Because when our community comes in, you have BIPOC skaters, you have trans skaters, you have gender-nonconforming skaters. It’s, like, unreal.”

Madrid is one of the cofounders of OnWord Skate Collective, a local skate crew that welcomes skaters of all ages and all abilities, prioritizing women, trans, nonbinary, and gender-nonconforming people, and anyone else who identifies as LGBTQ+. 

When OnWord hosts a meetup, they start with introductions, pronouns, and positive affirmations. Skaters go around the circle and say things like, “I am enough.” “I’m a badass.” “I will bring authenticity and love into everything that I do.” It creates a sense of safety and community for those not typically welcome at skate parks.

OnWord was founded in January 2021. In typical pandemic fashion, it began over Zoom, with big ideas spoken through screens and a thrilling sense of potential. Madrid and cofounders Bridget Johnson, T Smith, Cath Hodge, and Deb Hwang received a grant from the School of the Art Institute of Chicago (SAIC) to build a DIY skate park. Madrid, then an architecture student, took the lead on designing individual elements like custom beginner-friendly ramps and rails, and then fabricated the parts in SAIC’s wood shop. OnWord participants swapped power-tool tips as well as skate tricks, and they constructed their own skate park. 

They called the project OnSite, and it was the perfect outlet to experiment with skateboarding, inclusive design, and community-building. The first day they built it, and the second day they skated it. Filmmaker Johnson documented the experience on camera, saving Zoom recordings and conducting in-person interviews along the way for a short film.

DuWayne Padilla for Chicago Reader

OnSite was a success, and so was the short that came out of it. The original Breaking the Barrier is full of interviews and action shots of OnWord skaters building the park and skating together; there are young skaters in elbow pads and knee pads, pronoun stickers and top-surgery scars, and an overwhelming amount of queer joy. After a sold-out showing at the Martin, an artist-first event space in West Town, the movie won best documentary short at the Music Box Theatre as part of Premiere, DePaul’s film festival.

But the OnWord crew were far from finished. OnSite and the short film seamlessly paved the way for more changes in the skating world—and for a much bigger film.

“This [SAIC] grant really just allowed us to turn one singular project and one singular event into an entire collective,” Madrid says. They skate together, sure, but in Madrid’s own words, OnWord is first and foremost a community. “It’s a space for skaters—the community of skaters that we have—to share resources, to learn from each other, and also to just hang out and have a good time, and feel included in a skate park.” 

It’s often difficult for nontraditional skaters—anyone who isn’t a white, cisgender, straight man—to find role models and feel welcome in skateboarding. Like some of the OnWord founders, I picked up skating during the pandemic. I live in Uptown near Wilson Skate Park, but I’ve only ventured over a handful of times, and only at non-peak hours. As a queer female and a beginner, I find myself sticking to the adjacent parking lot instead of braving the park itself, feeling a strong sense of unworthiness. And I’ve been lucky—most of the Wilson skaters seem to ignore me, but some women experience direct harassment or inappropriate behavior surrounded by so much toxic masculinity. 

That harassment and the accompanying senses of isolation and unworthiness are exactly what the founders of OnWord want to eliminate.

The OnWord crew host skate meetups and teach lessons; they utilize Madrid’s skills in architecture to teach skate park building and construction; they’re big on skill-swaps, where roller skaters and skateboarders switch wheels and help each other learn; and they also organize events like clothing drives, social hangouts, and town hall conversations.

This work and the relationship-building with OnWord skaters helped Johnson realize that there was potential to turn Breaking the Barrier into a full-length film. It will be the first feature film to come out of her company Dare to Dream Productions, which seeks to tell authentic and positive queer stories with inclusive practices. Like the short film, the documentary will explore identity, equality, and community through interviews with OnWord founders and participants. 

Johnson speaks with such admiration for the OnWord members turned interviewees. “I love just seeing the joy in people’s lives that OnWord has brought to them,” she says. “How they look forward to our meetups on the weekends, and how we’ve kind of become like a family that’s not just about skateboarding.”

Breaking the Barrier will also highlight accessibility, with a broad focus on the south and west sides.

“I think something that we like to keep in mind is that the type of spaces that we wanna create don’t have all that much impact if the people we’re tryna reach can’t get to it,” says Smith, one of the founders. “So it’s been super important for us to be mobile, especially in a place like Chicago where it’s super segregated, where a lot of people don’t even necessarily feel comfortable going to certain areas just because it’s unfamiliar to them, or they don’t have a car to get there, or they might have to leave the event at night.”

Chicago has plenty of LGBTQ+ community resources, but they’re disproportionately on the north side. “Then, everybody else is kinda just left out,” says Smith. “Even if you can get there, in terms of transportation, I think having something centered on the north side sends a certain type of message to various communities.”

And they’re correct—the city doesn’t have any skate parks south of 31st Street, and most of the well-known skate shops like Uprise or Wilson Yards, for example, are on the north side, which means that huge portions of Chicago don’t have access to skating resources and spaces. Burnham Skate Park on 31st is one of the only parks not located up north. “Burnham was not even built or designed by skaters,” Madrid says. “The people who made that were, like, a sidewalk company. So there are ginormous holes in the skate park where your wheels can get caught. And that’s so unfair, you know what I mean?”

DuWayne Padilla for Chicago Reader

OnWord wants to get funding for a truck, large enough that they can transport their mobile skate park anywhere. (For now, it lives in Madrid’s garage.) They also want to transport their film. After the festival circuit, OnWord wants to bring Breaking the Barrier to Chicago public schools and local LGBTQ+ groups. They plan to screen the film and offer Q&A sessions, host interactive skate workshops, and create safe, open spaces for young queer people to talk about identity and belonging. 

It will also be a full-circle moment for Johnson as a filmmaker. “Creating my first feature film has always been my dream since I was 12,” says Johnson. “I’ve met some beautiful souls during this journey so far, and I’m looking forward to meeting more, especially getting the opportunity to showcase the film at schools. I can’t wait to go back to my old elementary school and see my old teachers who encouraged me to follow my dreams.”

On paper, Breaking the Barrier’s target audience generally includes teenagers to 30-somethings, the skateboarding community, and Chicagoans, given its rootedness in the city’s people and physical spaces. However, that’s another barrier the filmmakers want to break.

“We’re hoping to connect to a bigger audience,” Johnson notes. “Because it’s not just about skateboarding, but finding a safe space and what community means to a variety of different people in Chicago.”

“I want everybody to see it,” Smith adds. “I want everybody to hear it.” 

They continue, “When I talk about OnWord and what we do and why we exist, I always say: If you were to have a conversation with someone and ask them to picture a skater, they’re probably not gonna picture most of the people that show up to our events. So we wanna challenge that, we wanna go beyond that norm, we wanna break that stereotype of having a certain image when you think of a skater. Literally anybody can skate! And anybody does skate, right?”

And that’s the deal—anybody is welcome at OnWord. Breaking the Barrier will be a reflection of that inclusivity, and an example of the power of films made by queer people, of queer people, for queer people.

When Johnson was first discovering her sexuality, she leaned on her love of film. Like many people, however, she felt overwhelmed with queer media depicting tragic endings, breakups, and often death. Johnson knew that Breaking the Barrier should be feel-good and inspiring instead. 

“Maybe skateboarding is not for everyone, but there’s always something that you’ve always wanted to do, and hopefully this film empowers people to wanna actually pursue that,” she says. “We want to be the representation and role models we never had growing up.”

DuWayne Padilla for Chicago Reader

While audiences will eventually see the accomplishments of OnWord in front of the camera, the filmmakers also want to ensure that they’re approaching the work behind the scenes with similar intention. The film industry is known for grueling hours, low pay, and even hazardous working conditions, but OnWord’s collaborative DIY approach and commitment to working with diverse local filmmakers will combat this.

“It’s very toxic, how some film crews are run, and how you’re working 14-16 hours without very many breaks,” Johnson says. “And so what we’re trying to do is work less hours and also have more positivity on set.”

Through a mix of school connections and social media, OnWord has created a film crew made up of women and LGBTQ+ Chicagoans, most of whom are also skaters and share a passion for OnWord’s mission in the skate community.

OnWord’s last barrier? The funding. Lucia Agajanian is currently signed on as a producer for Breaking the Barrier. The team has an Indiegogo campaign set up to raise money for production, and they’ve been applying for grants and pitching the idea to get other producers on board. They’re hoping to carry the momentum of the short film and make some headway on funding this summer, all while keeping up with their usual programming.

OnWord will host OnSite 2.0 on August 6, 7, and 8, and have a chance not only to build a new DIY skate park, but also to conduct more interviews and really flesh out the documentary. The finished Breaking the Barrier will go all the way back to those early Zoom calls between the cofounders, ending with this product of their tremendous efforts.

“The film will really start with the origins of OnWord, and then [go] to wherever we end up,” Johnson says. “Like I think that’s the beauty of it—we’re kinda just following our skaters and seeing where life takes them.”

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Camae Ayewa, aka Moor Mother, has always been one to cite her sources. In addition to performing as a member of Philly-based free-jazz collective Irreversible Entanglements, the contralto wordsmith has frequently paid homage to the jazz, blues, and gospel canons in her solo work, beginning with her 2016 debut, Fetish Bones, and continuing through last year’s Black Encyclopedia of the Air. Ayewa described those canons in a 2021 interview with Pitchfork: “Not only is it Black American classical music, but it’s also a liberation technology.”

Moor Mother’s new album, Jazz Codes (Anti-), is a collage-style tribute to Ayewa’s musical forebears. She conceived it as a companion piece to Black Encyclopedia, and Jazz Codes is undoubtedly the clumsier sibling. While it’s a solid record for Moor Mother novices, and there are plenty of bangers throughout, Ayewa’s verses lack the freshness they have on previous releases—missing are the white-hot fervor and spontaneity of Fetish Bones and the volleying wit she showcased on Brass, her 2020 collaboration with rapper Billy Woods of Armand Hammer. 

Too often, Jazz Codes is blatantly, underwhelmingly on the nose, with heavy-handed samples and stilted lines such as “Be sharp / So sharp. . . . See sharp / Be natural” (from “Ode to Mary,” a nod to jazz pianist Mary Lou Williams). “Meditation Rag” is a particularly sore thumb; its verses SparkNote a century of jazz history with a wink and a nudge. That’s not to besmirch the sonic makeup of Jazz Codes, though. Ayewa has assembled remarkable collaborators: harpist Mary Lattimore, pianist Jason Moran, flutist Nicole Mitchell, and her Irreversible Entanglements compatriots, to name a few. But as far as Ayewa’s love letters to Black American music go, it doesn’t get better than the Brass track “The Blues Remembers Everything This Country Forgot.” That one still gets truer too.

Moor Mother’s Jazz Codes is available through Bandcamp.

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Reader senior writer Ben Joravsky riffs on the day’s stories with his celebrated humor, insight, and honesty, and interviews politicians, activists, journalists and other political know-it-alls. Presented by the Chicago Reader, the show is available by 4 p.m. Tuesdays through Fridays at chicagoreader.com/joravsky—or wherever you get your podcasts. Don’t miss Oh, What a Week!–the Friday feature in which Ben & producer Dennis (aka, Dr. D.) review the week’s top stories. Also, bonus interviews drop on Saturdays, Sundays and Mondays. 

Chicago Reader podcasts are recorded on Shure microphones. Learn more at Shure.com.

Chicago Reader senior writer Ben Joravsky discusses the day’s stories with his celebrated humor, insight, and honesty on The Ben Joravsky Show.

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