In a scene full of big personalities, Jim Post was a giant

Since 2004 Plastic Crimewave (aka Steve Krakow) has used the Secret History of Chicago Music to shine a light on worthy artists with Chicago ties who’ve been forgotten, underrated, or never noticed in the first place.

Once again, Chicago has lost a legendary musician, and in this author’s opinion there haven’t been nearly enough public tributes. Jim Post was a crucial part of the Old Town folk scene in the 1970s, but compared to John Prine, one of his contemporaries on that scene, he’s barely been memorialized. Both men had long, productive careers, and I’d argue that Post took more interesting twists and turns on his path—he even had a hippie-era hit song with the duo Friend and Lover. But there’s no need for comparisons. Post was very much his own man, and a real character too.

Jimmie David Post was born in Houston on October 28, 1939, and grew up outside the city in southeast Texas. In the liner notes to a 2005 reissue of Friend and Lover’s sole LP, Post explained his upbringing to author Richie Unterberger: “I lived in 100,000 acres of forest,” he said, “about five to ten miles up the river from the San Jacinto Battleground where Texas won its freedom.” He started out by singing gospel at Baptist revival meetings, and at age six he won a broadcast radio competition. At that point, the die was cast, and Post was a performer for life. 

As a young man Post joined Houston folk group the Rum Runners. “Our first tour was the Playboy tour, so I went from singing church music revivals to the Playboy tour,” he told Unterberger. A 1964 Rum Runners gig at a fair in Alberta, Canada, would alter the course of Post’s life. He met dancer Cathy Conn, who was performing at the same event, and was instantly smitten. She lived in Chicago Ridge, just southwest of the city, and in short order Post packed up and moved here. 

The couple threw caution to the wind and married within a few months. As the musical duo Jim & Cathy, they started playing the north-side folk scene, though the term “folk” never sat quite right with Post. “I didn’t know I was a folk musician until I went to Chicago, and some people at the Old Town School of Folk Music said, ‘Well, you’re a folk singer,’” he told Unterberger. “But there’s a difference between a folk singer who grew up in Chicago and decided to be a folk singer, and someone who grew up in the deep woods, going to those revival meetings and those dances and stuff, and coming straight out of it. We didn’t think of it as folk music.” 

The duo drew good crowds at the Earl of Old Town, the epicenter of the local folk scene, and soon signed with Chess Records subsidiary Cadet. They released one single as Jim & Cathy, 1966’s “Santa’s Got a Brand New Bag” b/w “People Stand Back” (both written by Post), and neither exactly set the charts on fire.

In an attempt to keep up with changing trends, the couple renamed themselves Friend and Lover—Post was the friend, Conn the lover. They released one single on ABC Records (“A Town Called Love” b/w “If Tomorrow”), then went to New York to audition for Verve Records executive Jerry Schoenbaum. “He said, ‘You have to send me a tape, ’cause I never listen to people in person, because I’m affected by the way they look,’ which is kind of strange when you think about it,” Post told Unterberger. “I said to him, ‘Well, why don’t you turn and look out the window, and we’ll sing for you?’” When Schoenbaum turned back around, there was a big smile on his face. The duo ended up getting signed. 

The Verve Forecast imprint sent Friend and Lover to Nashville to record with future star Joe South (of “Games People Play,” “Walk a Mile in My Shoes,” and other soulful pop hits). At the session, the couple cut what would become their only hit, “Reach Out of the Darkness.” The song was inspired by a Central Park love-in they’d attended: “When we left, I had two lines written on a napkin,” Post told Northwest Quarterly magazine in 2008. “‘I think it’s so groovy, now, that people are finally gettin’ together,’ and ‘reach out in the darkness.’” (The record company missed that crucial “in,” which Post and Conn clearly sing in the song, and titled it with an “of.”)

Friend and Lover’s sole hit, “Reach Out of the Darkness”

“Reach Out of the Darkness” is unusual for a rock number—it uses a bass as the lead, and it has no verses. “In musical terms, it’s all choruses and refrains,” Post told Unterberger. “The bass player didn’t have any idea what to play, and I didn’t. You gotta realize, I knew nothing about rock ’n’ roll. I was really in church music and backwoods music; that’s where I grew up.” He ended up humming a line for the bassist to play, which nearly duplicated the melody. Ray Stevens (who’d later release “The Streak”) played keyboards and arranged the strings.

Released in fall 1967, “Reach Out of the Darkness” didn’t become an anthem for a generation until months and months later, in summer 1968. A great deal of dubious lore surrounds the timing of the song’s success. One of my favorite stories, which I can’t verify, concerns a manager or promo man who cranked it from a sound truck near a sit-in to protest the draft at Golden Gate Park (or outside the park’s Kezar Stadium, where thousands of students who’d been arrested at the sit-in were being held). Supposedly this savvy operator also plied Bay Area radio stations with copies of the infectious flower-power tune. 

The song fell off the charts quickly, but it’s had a long life: in the late 80s and early 90s, it was famously sampled by Biz Markie and by the trio Krush, and it’s been used in a long list of movies, commercials, and TV shows, including the original Beverly Hills, 90210 in the 90s and the sixth season of Mad Men in 2013.

On the strength of that hit, Friend and Lover recorded their only album, also called Reach Out of the Darkness, but the sessions suffered from session-drummer snafus and South’s declining interest. Post himself wasn’t a fan of the record, but I enjoy a lot of it—“Ode to a Dandelion,” also released as a B side in 1968, is primo acid folk (long before the genre had a name). I also like some of the Friend and Lover singles that followed, like the driving, psychedelic “Circus” from 1969. Their last release was the soulful “Hard Lovin’” b/w “Colorado Exile,” which came out in 1970, the same year the couple broke up and took the band with them.

Post briefly lived in Colorado and San Francisco before returning to Chicago in the early 70s. In San Francisco, he hooked up with Fantasy Records, which would release his first several solo LPs. The 1972 LP Slow to 20 was the first, showcasing Post’s savvy with blues, folk, and pop. 

Jim Post performing with Steve Goodman and Rita Coolidge at the Earl of Old Town in 1972

During this period Post became one of the leading lights on the Old Town folk scene, alongside Prine, Steve Goodman, Fred Holstein, Bonnie Koloc, and Corky Siegel. His 1973 solo LP Colorado Exile captured the charm of his high, keening voice and his earthy story-songs, with their clever lyrics and countrified tinges—it easily could’ve made him the next John Denver or James Taylor. But Post was convinced Fantasy didn’t promote the album enough. 

The entirety of Jim Post’s 1973 solo album Colorado Exile

He also admitted that he missed some opportunities himself. “Merl Saunders was playing for me, and he said, ‘I played the work tape for Jerry Garcia, and he wants to play on your album,’” Post told Unterberger. “And I said, ‘Well, I already have a guitar player.’” Garcia would release Old & in the Way with a top-shelf bluegrass band later that year, giving Post plenty of reasons to regret his decision. 

Having lost faith in Fantasy, Post moved on after 1974’s Looks Good to Me, and by his own account “gave up on commercial music.” For the excellent 1977 LP Back on the Street Again, he worked with Mountain Railroad Records, based in Cambridge, Wisconsin. The live album, recorded at several northern Illinois venues, features strong, heartfelt originals such as “Walk on the Water” alongside tunes by more obscure contemporaries, among them Dwain Story and Thom Bishop (both previously covered in Secret History). 

The title track of Jim Post’s 1978 album I Love My Life

His second and last release for Mountain Railroad, the 1978 studio album I Love My Life, has a more commercial sheen. Somewhat infamously, it features Post wet and shirtless on the cover (possibly under a waterfall), with his glorious full mustache soggy and drooping and a carefully neutral expression on his face that contrasts hilariously with the title.

In 1979, Post began a relationship with Chicago roots label Flying Fish, but he was also about to open up a whole new path in his career. In the early 80s, he settled in Galena, Illinois, which inspired him to create his first one-man show. Galena Rose: How Whiskey Won the West, which he wrote in 1986, was solo musical theater that presented gritty history and wild folklore in a ground-level view. “More than history, the show is a collection of songs and patter—the kind of music and stage talk that has made Post one of the most theatrical of our singer-songwriters,” Reader critic Hank De Zutter wrote in 1988. “The strength of the show is Post’s cornucopia of original music, a rich, simmering stew.” 

Audience footage of Jim Post performing a song from Galena Rose at the Galena Center for the Arts in 2019

Even opera star Luciano Pavarotti loved Galena Rose. According to Rick Kogan’s obituary for Post in the Chicago Tribune, Pavarotti found him backstage after a show and told him, “You have the voice of an angel. You should have been an opera singer.”

This led to other such productions in the early 90s, such as The Best Damn Songs (Most People Never Heard), a memorial of sorts to his departed folk pals Steve Goodman and Stan Rogers. An Evening in Old Town also paid tribute to Chicago’s bygone folk scene: “Between songs Post reminisces about the early days,” wrote Reader critic Mary Shen Barnidge in 1994, “performing in Old Town clubs in the company of artists whose concert posters and album covers decorate the wall behind him—Steve Goodman, Fred Holstein, John Prine, Thom Bishop, Bryan Bowers, Tom Dundee, humble sideman Stephen Wade, and Bonnie Koloc.”

For his next act, Post created a beloved portrayal of Mark Twain (in Twain’s day, Galena was served by a busy steamboat port on the Mississippi). He wrote Mark Twain and the Laughing River and debuted it with a backing band in 1996; later in its long run, it was usually a one-man show, with just Post’s guitar or banjo and his goose-bump-raising voice. 

Jim Post performs a song in character as part of Mark Twain and the Laughing River.

“The tunes, belted out in Post’s clarion country-gospel tenor, are catchy and charming,” wrote Reader critic Albert Williams at the time. “The hilarious, insightful stories and aphorisms convey Twain’s amusement at the foibles of human nature. . . . Post’s mischievous, slightly show-offy foxy-grandpa persona is irresistible.” He traveled widely to appear as Twain, and the role won him an American Library Association Award in 1997.

That same decade, Post got involved in children’s entertainment. Maureen O’Donnell shared his thoughts on the subject in her excellent Sun-Times obituary: “Performing for kids,” Post said in 1990, “is like performing for happy drunks.”

In the early 90s Post launched the children’s show Cookie Crumb Club at the Organic Theater Company in Chicago, and in the 2000s he wrote kids’ books with his wife Janet Smith (he’d eventually marry four times). Post and Smith also worked together on Breaking the Sounds’ Barrier: Reading by Ear, a series of songs and books designed to help kids learn to read phonetically.

The Jim Post original “Walk on the Water/An Old Story,” from the 1977 live album Back on the Street Again

Post appeared at a concert celebrating the 40th anniversary of the Summer of Love in 2007, alongside the likes of beat poet Michael McClure, Ray Manzarek of the Doors, psychedelic originators the Charlatans, and Country Joe McDonald and Barry “the Fish” Melton (the event spawned a box set of two CDs and two DVDs). Post also continued recording albums—the last was 2009’s Reach Out Together—and even after he stopped adding to his discography, he kept gigging. Over the past two years, though, his health declined dramatically, and he died of heart failure on September 14, 2022, while in hospice in Dubuque, Iowa. 

Post is gone, but his rich body of work and outsize personality live on in his fans’ hearts and record collections. O’Donnell recalls that Post used to end his gigs by reminding the crowd, “If you keep coming to see me, I’ll never get a real job.” He never did—and we were all better off for it.

Special thanks to Ken Voss and Richard Friedman for sharing their knowledge.

The radio version of the Secret History of Chicago Music airs on Outside the Loop on WGN Radio 720 AM, Saturdays at 5 AM with host Mike Stephen. Past shows are archived here.


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An Evening in Old Town

Mark Twain and the Laughing River

Cookie Crumb Club

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