Depending on how you want to look at it, Reilly has been working on Mister Romantic since the pandemic, the mid-2000s, or the age of eight. Growing up in Chicago, he regularly starred in musicals as a kid. “That’s all I did,” he says, “just one after the other.” After high school, he was accepted into the acting program at DePaul University and shifted gears: “I just decided, like, Oh, that’s not what serious actors do.”
In his 20s and early 30s, Reilly established himself as an everyman with gravitas, with key roles in hit indies like What’s Eating Gilbert Grape and Boogie Nights. Then he was cast in Chicago to play Amos, a.k.a. Mister Cellophane. His soulful performance earned him an Oscar nomination.
“I realized, Wow, I can already do this—I grew up doing this—and not only is it worthwhile and a valid thing to do, but you have to be pretty fucking talented to do this,” Reilly says. “It’s not something that every dramatic Method actor can do. It gave me this deeper appreciation for it.” When filming finished, Reilly felt incomplete. He couldn’t just jump from movie-musical to movie-musical—they don’t make enough of those, though he’s long dreamed of playing Sweeney Todd—and he had a thriving film career. He’d awakened this quiet side of himself, and had nowhere to put it.
Even as he became John C. Reilly, screen star—taking on Adam McKay’s studio comedies Talladega Nights and Step Brothers, leading a parody classic in Walk Hard, letting his freak flag fly in Tim and Eric Awesome Show, Great Job! as the unhinged newscaster Dr. Steve Brule—he started focusing on music. He formed a few bands, and at one point, sang Irving Berlin’s 1923 heartbreaker “What’ll I Do” at the Largo. He was moved by the experience of performing a song about eternal love, the same way he felt doing “Mr. Cellophane” in Chicago. So he collected songs like it, one by one, and built a set list. Two, actually.
Reilly had to wait, though, to finish the biggest acting commitment of his career. For two seasons on HBO’s Winning Time, he played the lead role of Lakers owner Jerry Buss, a process that took longer than he expected due to COVID delays. He filmed the second season finale (which turned out to be the series finale) on a Friday early last year, and performed his first show of Mister Romantic that Monday. “It’s the longest I’d ever been employed by anyone, and I was really itching to just be free again and express myself,” he says. “And also, I just felt like the world had gotten so hard to deal with. I felt like there was this real crisis of empathy, or lack of empathy.”
Reilly carries an earnestness that’s exceedingly unusual in Hollywood. “All I’ve ever known how to do is be sincere with my acting, and it’s never let me down,” he says. “You might not like what it is, but you can’t say it’s not real. You can’t say it’s not true.” This goes even for his silliest characters, like Walk Hard’s Dewey Cox or Tim and Eric’s Steve Brule. It’s a way of getting out of his own way. “I’ve always been someone who doesn’t really like myself, my own personality, my own thoughts. I’m always more comfortable hiding behind a character.”