
Steve Wynn/Photo: Guy Kokken
In his song “Tell Me When It’s Over,” Steve Wynn questions the statement that “it’s a waste… not to learn from mistakes.” He was already challenging the impact one decision, or mistake, can have on the trajectory of a life in a song written in his twenties, and appearing on the first Dream Syndicate album. Like one of his songwriting heroes Ray Davies, Wynn was already an old soul in his youth pondering choices he, or those in his life, have made.
Fast-forward, after writing more than 300 songs and performing thousands of live shows in more than twenty-five countries as part of The Baseball Project, solo or with his Miracle Three, Wynn continues to look back, asking “What if I changed that one thing, would my life be different.” Always a storyteller—Wynn was an award-winning sports journalist all the way back in high school—his memoir “I Wouldn’t Say It If It Wasn’t True” (Jawbone Press) provides an entertaining and thought-provoking self-analytical ride-along with his life and career through the 1988 breakup of The Dream Syndicate.

Steve Wynn, “I Wouldn’t Say It If It Wasn’t True”
Wynn had “thought about writing a book” or more accurately, had “always wanted to have written a book.” Unfortunately, making thirty-three records and writing all of those songs “got in the way.” Faced with the pandemic and hanging out in his house in Jackson Heights, Queens “with a lot of coffee and time on my hands” he was able to set his life to words at the speed of 2,000 to 4,000 words a day. In addition, he and his wife and bandmate, drummer Linda Pitmon, provided a musical lifeline through live-on-the-web performances—many of which are still up and worth watching. (One to check out on YouTube is his and Pitmon’s version of the Velvet Underground’s “Rock and Roll” with special guest Jason Victor).
Among many enchanting stories shared in the book, he crossed the country by bus to meet and drink heavily with another cult artist and musicologist, Alex Chilton, and credits Bruce Springsteen with convincing Wynn that he could have a future as a rock ‘n’ roll storyteller:
“It was revelatory. All of Bruce’s patter and storytelling felt like it was conjured in real time, as though the giant arena was a backlit coffee house where Bruce was talking to a handful of friends, while the music itself was larger than life: mythic, heroic, with arrangements that jolted the system with surprise. It was an I didn’t know you could do that experience.”

Steve Wynn, “Make It Right”
Wynn’s own performances as a solo artist with nothing more than an acoustic guitar are incredibly intimate. Given the power of many songs in his repertoire, it is surprisingly satisfying how well Wynn comes across as a lone troubadour. As he explains it, when he plays solo he is “jamming with the audience… feeling them every second [he’s] onstage. There’s a push and pull to what I’m doing and how I sing and play that feeds off what I perceive they’re feeling.” Coming to The Hideout on October 20, Wynn will not only share his book, but will share his first solo album in over a decade, “Make It Right” (Fire Records).
He found himself “writing and recording songs inspired by the memoir I was putting together. With each chapter, I would get ideas for songs inspired by the deep dive into my past and vice versa. So, while the book is not intended to be ‘a sonic counterpart,’ the songs share similar autobiographical theme: ‘how we think about people, why do you make the decisions you do, jealousy, and pride.’ The album is like a Venn diagram inhabiting the overlapping questions of “Would I do anything differently” and, what would Wynn do if he could? Thankfully, Wynn comes from the old school of creating whole albums with an A and B side—taking listeners from Santa Monica (where he grew up) to Roosevelt Avenue, Queens (where he lives today). The new album has an arc and feeling many albums don’t have today—where all songs are equally important and make you a traveling companion.
Between California and New York is, well, Chicago, and Wynn is no stranger here. His grandfather’s brother had a clothing store in Chicago—Jack Robbins Clothes of Distinction. And, back in 1982, he played his first show at Tut’s (Belmont and Sheffield, upstairs where Milio’s Hair Studio is today) with The Dream Syndicate, and performed both solo and with several of his bands over the years at multiple places, including a faux Hideout internet show. Part of his mantra is also to bond with the city in which he is performing, “understanding the groove and speed of the terrain.” Just like his relationship with an audience, he “jams” with a city, feeling the push and pull with and against the elasticity of a bustling metropolis.
At the upcoming Hideout event, Wynn will jam with the city and audience as a triple threat—it will be a night of storytelling and songs—with reading and a Q&A, facilitated by Chicago indie-guitar hero Rick Rizzo of Eleventh Dream Day, who, hopefully, will join in for a song or more. You can expect to hear music Wynn wrote from the age of nine—the first song he wrote—through the end of the Dream Syndicate in 1988, as well as cuts from the new album.
Wynn’s Instagram handle is “Cultartist” which kind of tells you a bit about how he perceives himself on the spectrum of rock stardom. But, new cult members are welcome, and you don’t need to be familiar with his résumé to have a blast at the Hideout, reading his new book or listening to his new album. As he puts it, “new fans come along all the time. Younger people discover [me] on Spotify as a cult artist for everybody.” Wynn views his book, life and music is for everybody—anyone that fell in love with a song that rings true or has any love of music.
You won’t need to learn from any mistake if you check out his current album, memoir or Hideout show.
Steve Wynn reads and performs on Sunday, October 20, 8:30pm at the Hideout Chicago, 1354 West Wabansia, hideoutchicago.com. (21 and over.)
Bart Lazar is a Chicago-based independent music journalist, vinyl DJ, playlist creator and concert producer. Bart has a monthly residency at Sportsman’s Club where he educates hipsters on fifty years of independent music. In addition to Newcity, Bart’s writing can be found on his blog, www.oldpunksrule.com and his book “Declaration of (Dis) Interest” is available on Amazon. By day, Bart is a partner at Seyfarth where he is one of the nation’s leading advertising, data privacy and intellectual property attorneys. Contact: bljet331@gmail.com


