Culture
John C. Reilly talks Chicago, John Prine, Americana, seizing “courage” to release debut album at 60
By: Ian Saint
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NASHVILLE, Tennessee (WOUB) — John C. Reilly is reputed for blockbuster historical films like Gangs of New York and Chicago, the Jazz Age musical centered in his hometown. Today, the EGOT nominee performs The Great American Songbook on tour as Mister Romantic; whose debut album, What’s Not to Love, was released last year.
Reilly subsequently hosted the 2025 Americana Music Honors & Awards at Nashville’s Ryman Auditorium, followed by Americanafest’s keynote conversation with Jack White — where they spoke with WOUB’s Ian Saint about The White Stripes’ Rock & Roll Hall of Fame induction.
Americanafest 2026 takes place in Nashville from September 15-19. PBS will televise their award ceremony later this year.
A transcript of Saint and Reilly’s 2025 Americana Honors red carpet interview, edited for length and clarity, follows.
Ian Saint: How does hosting Americana Honors at The Ryman feel?
John C. Reilly: The staff behind the scenes here is incredible. With a bill this big, it’s amazing that this thing comes off every year. I’ve been here before — I gave Album Of The Year to John Prine (in 2019). That was an incredible honor to give him. This time I’m like the rodeo clown, just keeping the thing moving. And I get to do a couple songs with a couple of people. It’s great to mix it up with all these musicians: John Fogerty, Emmylou Harris, Dawes, Daniel Lanois…. It’s an incredible cast. It’s a big honor to even be in the same room as those kinds of people.
Ian Saint: Something I’ve always admired about your career is how many extensions you’ve embraced — a wide stylistic range of films, TV, theater, and now a music album. I think it’s easy for folks to get discouraged from trying new things publicly, with social media and comparison games.
John C. Reilly: A big, core belief of mine is that everyone should do everything artistic that they want to do, or that they feel they have inside them. Even if it doesn’t end up going out into the world or whatever. Like, if you’re a garbage man and you’ve got a poem in your head, write a poem — it can only make the world a richer place.
Ian Saint: Your debut album came out the year you turned 60. How does it feel to have this new extension of your wide career at this stage of your journey?
John C. Reilly: So many of us get (lost) in our own heads. It took me a long time to get the courage to make this record; but if you can just get past that, and not hide your light under a bushel, it’s a good thing for the world for all of us to express ourselves in that way. So yeah, the record coming out was a huge moment for me personally, and for the band. It’s been about three years that we’ve been doing Mister Romantic, and it’s a really great taste of the show — (although) the album is its own experience.
Ian Saint: Are there particular songs you’ve noticed resonate with audiences in ways that surprise you?
John C. Reilly: Well, every song resonates with the audience because the songs I picked are these eternal melodies that are so beloved — you know, songs by Irving Berlin, Nat King Cole, Frank Sinatra, Tom Waits, Louis Armstrong. That said, a lot of younger people in the audience have never heard them before; so that’s a really exciting part, sharing the music with the next generation of people that might’ve just come to the show because I was in Stepbrothers or something. The songs that really stick with people, I think it depends on what moment you’re in your life — I can see different people connecting at different moments. The show is mostly about falling in love or trying to connect with other people.
Ian Saint: Which one personally resonates most with you?
John C. Reilly: I really, really love “I’ll Be Seeing You.” I always get really emotional when I sing it. There’s something so beautiful and timeless about it. “I’ll be looking at the moon, but I’ll be seeing you.” It’s so romantic.
Ian Saint: How was presenting John Prine with Album Of The Year in 2019?
John C. Reilly: I’m glad he lived to receive that, only six months before we lost him to COVID-19. I’m from Chicago, where John was a postman for a while, and he got his start in those folk clubs around Wells Street and North Avenue. So for me, it was like shining light on one of the good guys. Also, it wasn’t just a legacy artist who made great records in the past — that last record he made (Tree of Forgiveness) is one of my favorites. It was a huge honor just to meet the guy, you know, in any context; but I got to stand on stage and say, we appreciate you — that was a special moment.
Ian Saint: I was just in Chicago for the Oasis reunion, and it was one of five consecutive nights of Soldier Field shows. A jazz festival was going on simultaneously; and I was so impressed by how both vibrant and orderly the city was — odd to juxtapose that impression with the president sending the National Guard there. What is something about Chicago that you’d like more people to know?
John C. Reilly: I didn’t leave Chicago until I was 22, other than little car trips with my family. To me, it’s one of the crown jewels of America. New Orleans and Chicago, in my mind, are competing for the most amazing, unique places in America. I think most people that come to Chicago are shocked by two things. (First,) how nice people are — there’s this Midwestern folksy charm, and lack of pretension to people in Chicago that’s just wonderful. It’s not so aggressive as New York City, and not so spread out as Los Angeles.
Of course everyone’s heard about the wind in Chicago, but I think what really surprises people is that lake view — like an inner coast, a coastal city in the middle of the country. People hear “lake” and think it’s this little circular thing you can swim across, but Lake Michigan is massive. (First-time visitors remark) “Gosh, it looks like the ocean” — but you don’t taste salt when you swim there.
Ian Saint: I always say, seeing that extraordinary lake view is what makes connecting at O’Hare worthwhile — because it’s not O’Hare’s punctuality.
John C. Reilly: There’s great hot dogs in O’Hare.
Ian Saint: That’s funny. I’m grateful I caught the Oasis reunion in Chicago, rather than NYC and LA — although I love all those places — for the traits you perfectly describe. Chicago really embraced Oasis with citywide fervor.
John C. Reilly: Yeah, because NYC and LA get so many great acts — they’re like, “We had Frank Sinatra here last week.” I find in smaller places, even Chicago, the audience is more excited you’re there.
WOUB’s CREATE channel airs Travels With Darley’s “Chicago Architecture & The Magnificent Mile” on Tuesday, September 29 at 10am, 5pm, and 11pm.