The Chicago suburb of Libertyville, Illinois, has produced the likes of Marlon Brando, Rage Against the Machine guitarist Tom Morello, Tool guitarist Adam Jones, politician Adlai Stevenson, and musician Ike Reilly.

Of those names, Reilly is likely the least known, and an upcoming documentary, Don’t Turn Your Back on Friday Night, shines a light on that fact.

“I think he’s the best American songwriter working right now,” Cracker’s Johnny Hickman says in the trailer.

“He’s an artist the world deserves to hear,” says Morello, who is also executive producer of the film and friend of Reilly’s.

And how does Reilly feel when hearing that kind of high praise?

“I have good friends. I think they mean it, but you know. That’s fine,” Reilly said in a phone interview with Whatzup. “There’s plenty in the film to balance it out. Interviews with my own kids will certainly balance out any of the compliments about being a songwriter.”

Along with a preview of what’s to come, the trailer also shows a slew of awards its received from the Toronto Documentary Feature & Short Film Festival, the Malibu Film Festival, and Hollywood Gold Awards, among others.

Don’t Turn Your Back on Friday Night hits streaming services on Tuesday, Aug. 27.

Before that, Reilly and filmmakers will hit the road to show it to audiences, including Thursday, Aug. 22, at Cinema Center. Along with the screening, the night will feature a discussion and performance from Reilly.

Talking music

Known for his straight-forward lyrics that have made him a fan favorite around Chicago and beyond, Reilly’s first playing gig was when he was just 13 years old. 

As he continued to play, he picked up jobs at a cemetery and hotel before opening Diamond City Studios in Libertyville.

Following a break from recording himself, Reilly got back into it. Some demos he recorded began to make the rounds and he was signed to Universal Republic Records, with whom he released Salesmen and Racists in 2001.

His debut was the lone release with Universal, and he’s since released seven albums with Rock Ridge.

Going deeper

So, there you have a little bit about Reilly’s musical journey. However, if that was going to be the extent of Don’t Turn Your Back on Friday Night, the documentary would not have been made.

“I had no desire to make a film about microphone placement or making a record,” Reilly said. “There is a little bit of stuff about the music industry in there, but that stuff is really boring to me.”

Instead, the film is a collection of home videos from as far back as 1965, showing the toll that following a dream can take on those around you.

“Objectively, it’s not a conventional rock n’ roll documentary,” he said. “I think they made it a little bit more profound about alcoholism and religion and being broke. 

“My whole goal was to be original as a writer. When you do that, it can be painful — you have to make sacrifices. We can put together a Clash cover band and go make a lot of money. The reward is the work, the songs, the camaraderie — the loyalty my band has shown me and I’ve shown them. You can wish for something your whole life and then never get into anything. We are very industrious people that have not sought or received the approval of the masses, but I’d put our band up against anyone’s live.”

That band is The Assassination, which includes guitarists Phil Karnats and Ed Tinley, drummer Dave Cottini, bassist Pete Cimbalo, organist Adam Krier, and the three newest members, Reilly’s sons Shane, Kevin, and Mickey on vocals. 

“I guess it’s kind of the like a punk rock folk revue where different people take the lead,” Reilly said. “I think of it as a communal type of thing. We’re a band of the people, ya know what I mean?”

And they’re a band with a very devoted fanbase.

“The people that come to see us, they’re not really passive fans,” Reilly said. “They’re all in. They know every word. It’s kind of a weird cross-section of generations. You’ll see moms and dads with their kids at our shows. It’s like the most unwholesome wholesome environment you can think of.”

Show it all

The devotion to the “lone troubadour” who leads “his greasy band” is clear, as his lyrics don’t beat around the bush. He commonly says, “My songs are either lies or apologies,” and they fit in perfectly at dive bars, such as our own Brass Rail, where he played in February and is featured in the documentary. 

“Some of my favorite footage is from The Brass Rail, to be honest,” he said.

Along with that footage, he also gave the filmmakers plenty more he had accumulated long before every one of our waking moments was being chronicled on our smartphones.

“There was someone always out on the road with us that had a camera, and that was dumb luck,” Reilly said. “It was never for any reason. It was like, ‘Oh, we have a camera. If you’re going to be tuning my guitars, turn it on and film from the side of the stage or bring it to the hotel room.’

“I gave them a ton of footage that people had shot, then they followed us around on the road and in the studio, and some at-home stuff. They found footage of my wife and I together that was in a shoe box on Super 8 film when she was 1-and-a-half and I was 4 — which is just crazy.” 

And while it’s fun to look back on footage, some of it could be difficult to watch, including his battle with alcohol.

“I know the story. Sometimes I don’t want to see it again, but it’s a necessary evil,” he said. “It wouldn’t be real (if we didn’t show it). Everything we’ve done is authentic and real. It was kind of the agreement I had with (co-directors) Michael O’Brien and Mike Schmiedeler: If you’re going to make it, make it about what my songs are about.”

The footage also chronicles his three sons’ involvement in the group, which came about as the family was stuck in quarantine amid the pandemic. 

With venues shut down, Reilly turned to the internet for The Ike Reilly Family Quarantine Hour to make ends meet. The effort went so well that his sons sang on the 2021 album, Because the Angels, and joined the band, having appeared with them during their 2022 performance at Middle Waves Music Festival at Foellinger Theatre.

“I’ve played with these guys (in the band) for 20 years or more. So, it was kind of strange that the kids started playing with us,” Reilly said. “They’ve been around these guys their whole lives. 

“My boys started writing songs and singing. We never pushed them that way at all. It was kind of like osmosis of being around musicians and artists their whole lives.”

Through music, his sons are following Reilly’s advice that we all need an outlet.

“Everyone needs some avenue or some vehicle to help them process things like the contradictions in the world, the injustices in the world,” he said. 

With Don’t Turn Your Back on Friday Night, audiences will see the avenues — good and bad — that they took. And perhaps, they will learn something about themselves in the process. As well as hear some good music.