We’ve Got A File On You features interviews in which artists share the stories behind the extracurricular activities that dot their careers: acting gigs, guest appearances, random internet ephemera, etc.

Earlier this year, John C. Reilly announced his debut album as Mister Romantic. For fans, it might’ve seemed like another project in a vast and multi-faceted career, but for Reilly it was the culmination of a yearslong dream to concoct a Vaudeville-esque show featuring many of his favorite songs. While Reilly has often been busy with music extracurriculars on the side of his already insanely busy acting schedule, What’s Not To Love? is the first time he’s made a full-fledged album for a personal project. This one is, fittingly, close to his heart.

Last month, the Mister Romantic show rolled through Franklin, TN, near where I live in Nashville. It’s a bougie suburb, and the Franklin Theatre convinced Reilly to split his two shows between afternoon and evening, since late-night events can’t really draw a crowd in that town. So at 4 p.m., I took a seat up in the balcony and watched the Mister Romantic performance unfold.

While Mister Romantic ostensibly presents a concert — backed by piano, sometimes guitar, upright bass, cornet, and violin while performing the American standards (and some later songs, too) from What’s Not To Love? Reilly does not perform as himself, however — he created a full-fledged character. The premise: Mister Romantic lives in a box, gets let out to perform a gig, and the only way he doesn’t have to go back in the box is if he can find someone to love him forever in the span of the show. This leads to a lot of spontaneous audience interaction as Mister Romantic/Reilly rushes into the crowd and excitedly (and maybe eventually desperately) interviews audience members to see if they could fall in love. At one point he came up to the balcony and was dangerously close to talking to me, but he instead picked a woman a few rows ahead, who was with her boyfriend, which led to a prolonged riff on love triangles.

“That guy owns the theatre, turns out,” Reilly says with slightly widened eyes and a dry, gruff chuckle when calling from Los Angeles. Apparently the dude wasn’t too put out, since he went backstage and said hello afterwards.

The Mister Romantic concert is both heartwarming and hilarious, and you should check it out if it’s ever near you. But this interview franchise was designed a long time ago to feature artists who had all sorts of odds and ends in their career. John C. Reilly is pretty much the king of that. Along with his calling cards like Paul Thomas Anderson’s ’90s films or Will Ferrell’s 2000s movies, Reilly has been involved in a truly daunting amount of art over the last several decades. Sure, he has iconic roles aplenty, but did you remember he was also in, like, Days Of Thunder? I didn’t. The man’s IMDB page is full of revelatory reminders, and that’s before you get to the array of musical activity he’s fostered in parallel to his film work.

On the occasion of What’s Not To Love?, out today, we caught up with Reilly to talk about how the project came to fruition as well as musical highlights from across his career — from singing bluegrass, to Walk Hard, to music moments in his filmography both iconic and obscure.

Mister Romantic’s What’s Not To Love? (2025), Singing “Mister Cellophane” In Chicago (2002), John Reilly & Friends (2010s), Playing Oliver Hardy In Stan & Ollie (2018)

You wrote that the Mister Romantic show emerged as a response to a tumultuous stretch of years. The idea was to spread “love and empathy,” and that the show came from both a place of “hope and despair.” You’ve had music endeavors throughout your career, but why did the impulse culminate in this character and show this time around, using these old standards?

JOHN C. REILLY: These are beautiful songs to me, songs I’ve loved for a long time. One of the things that triggered me wanting to do this kind of music and this kind of show was when I played Mister Cellophane in Chicago. That helped me rediscover how much I loved doing musicals. This music is in the wheelhouse for this sort of vaudeville performance. Though you’ll notice on the album, there’s quite a spread. It’s not just old stuff. We do Tom Waits. There’s an Eddy Arnold song, “You Don’t Know Me.” There’s variety, but the band and I came up with these arrangements that make them feel part of this Mister Romantic world even though they’re from different eras.

I had a bluegrass band for a long time as myself. There was something about it that was always a hard sell for audiences. You could tell sometimes people came out to see the bluegrass band because they were fans of Step Brothers. They weren’t fans of bluegrass. I realized I had to make sure people understand what it is they are coming to see. So creating a theatrical experience was something I was comfortable in and I felt communicated what Mister Romantic was.

Love songs are just the quickest way to touch people. You asked why I chose this kind of music, and the project defined itself, in a way. After Chicago, I was collecting songs for a long, long time. I have a pretty demanding day job, so a lot of things pushed it off. I didn’t have the full body of songs. I wanted every song to feel as inspired a choice as the rest. It took time for all these different songs to speak to me in this way.

The Tom Waits thing was interesting to me. He’s always had this out-of-time quality to his songwriting, and some of his songs have indeed become standards. But at the same time his own music can be more difficult than some of the other source material you’re working with here.

REILLY: He’s one of my all-time heroes. As a songwriter, as a modern artist, he has very few peers in terms of his ability to write stuff that feels like standards. His songs feel like they’ve always been here, somehow, even though they’re new songs. I don’t use a time period criteria. If something touches me and it has an eternal melody and something about it is unforgettable, and it feels emotionally in tune with where Mister Romantic is during every show, then I add it to the list. “Johnsburg, Illinois” is one of the all-time great love songs. When he does sing a love song, he really wears his heart on his sleeve. He’s very romantic. Think of a song like “Ruby’s Arms.” He explores being in love or wishing he was in love a lot in his music, so he was a natural fit.

You did have these other musical projects. You were singing in movies. You had the bluegrass band and did an NPR Tiny Desk. At one point I wondered: Why now? You’ve never made a full album for any of your other projects.

REILLY: The project wasn’t dreamt up to make an album, actually. It wasn’t part of the plan for me. The show is this crazy thing, with improvisations and crowd interactions and pantomiming. The music is the underpinning of the whole thing. In order to keep the momentum for a show going, to be able to tour and take it places, you do kind of need a calling card. I realized an album would be a great way to introduce people to the world and get them interested in coming to see the show.

I’d always been a little intimidated about making a record of my own. I’m not comfortable with this “actor sings your favorite songs” kind of thing. I didn’t want it to seem like a vanity project or some random thing where I’m doing cover songs. I wanted it to feel like a project that could stand on its own, an interesting exploration.

It takes a long time to have the courage to record yourself. Doing something for a movie, or a Tiny Desk — it’s less pressure, you’re putting yourself out there less. To produce an album, put it out to the world and say “This is how I sing,” it takes a lot of courage and time to get to that place, or to even find what that voice is. A lot of my life I’ve been someone who imitates people, whether it’s playing characters or when I was younger learning to play music and sing. I’d try to be like Bob Dylan, or try to be like Van Morrison, or try to be like Elvis Costello. It’s almost an apprenticeship in your mind, working through who your heroes are. After a while, you start to realize even if I tried to be Tom Waits it doesn’t sound like him anyway, so I might as well embrace who I am and bring my own interpretation to it.

The other thing that led me to making the record is I played Oliver Hardy in a movie called Stan & Ollie. He had one of the most beautiful voices I’ve ever heard. When he was younger, he had aspirations to be an opera singer, I think. When I was researching that part, I was looking for more of his music. He was singing for the movies, they must have recorded it. It’s not there. There’s only four songs or so, and it’s all from movies. I thought, what a shame. He’s such a hero of mine and here I can’t access one of his greatest talents. I thought, in case anyone’s interested in you as an artist or singer, you should leave this behind. Other people who did do that who really inspired me were people like Burl Ives, an actor who passed on so much music. It wasn’t just wanting to leave a part of myself behind, but also pass these songs along.

One of the big inspirations was Harry Nilsson’s record A Little Touch Of Schmilsson In The Night, this amazing covers record he did against the advice of the producer he worked with. He said he wanted to do all these classic songs he remembered from his childhood, mostly from the movies, and the producer was like “OK, good luck with that.”A number of the songs I sing as Mister Romantic, I learned from that record. One of the first songs I collected, I think the very first one where I thought this character could sing this song, was “What’ll I Do.”

I had noticed a lot of your bigger musical endeavors were from the 21st century. I know as a teen you had a band called Shark Fighter with your brother —

REILLY: You do have a file on me.

I don’t lie. So there are some musical moments in the ’90s, but I did want to go back to Chicago — was that really a fundamental pivot point not just about that style of performance but also wanting to do music more overall?

REILLY: Not so much. I was already doing music before that. But it was more like sitting in with friends at [the Los Angeles club] Largo. Chicago made me rediscover how much I loved that type of performance — very presentational, trying to connect with the audience, heart on your sleeve, very sincere. A lot of the different musical projects after that kind of culminated in Walk Hard. It wasn’t so much that I chose music, but people started to know I did music or that I could sing, so projects started asking me to do music.

When Walk Hard came along, I realized I had all these different songwriters and musicians I collaborated with. I was often rehearsing or doing a benefit and I thought I should join this all together. I should create something myself so it was central to my life. That’s what the instinct to start John Reilly & Friends was. Mister Romantic was the next thing I wanted to do.

But it’s not like I only listen to music from the 1930s or something. I’m super into hip-hop, I love newer folk and country music. I have broad musical tastes. But this is the current passion. The show was born out of joy and despair. Part of why I chose these songs was because I was looking for things that conveyed empathy or talked about love. If that was one of the big impulses to do the show, I needed to find songs that reflected that.

To me, they’re songs that reflect some sort of eternal human condition or wisdom. It’s reaching back into a different part of formative American art, but it’s like looking back to Greek mythology. We’ve always felt this way.

REILLY: My music company, the entity I run things through, is called Eternal Magic. I’m kind of fascinated by the eternal qualities of some music and why some songs survive and other songs are just contemporary. Out of all the millions of songs written and sung, how did “Amazing Grace” make it all this time? I think it’s not only the storytelling and words of these songs, but literally the chemistry of the notes. If this note follows that note and is resolved with this note, then it makes you feel like this. To me, that’s pure magic. There’s no explaining that in a logical way. Music just circumvents our brain and hits us right in the chest. I’ve always been captivated by that idea and exploring it.

Walk Hard: The Dewey Cox Story (2007)

Obviously this was going to come up, as this other moment where you created a music character. That movie has had a very enduring lifespan. It shows up on TikTok, a different generation has discovered it.

REILLY: I was at a Lakers basketball game one time and Glenn Frey was sitting a few seats away from me and he was like, “Walk Hard, man, that movie’s a documentary. If you think it’s crazy what you did in that movie you should’ve hung out with us in the ’70s.” I think a lot of musicians relate to the experience that character has even though it’s a satire, over the top. They just screened it in LA, and I went by and did an impromptu Q&A. Man, that movie had a lot of production value. Gospel choir and an orchestra and Don Was and Eddie Vedder? That movie is more well-done than it had any right to be — for a comedy, especially.

I wish Walk Hard had done better in the initial box office. We all had so many hopes and dreams poured into that movie. And months and months and months of songwriting and recording long before we started shooting. But what’s happened with that movie, is it’s now this cult phenomenon. I guess I could’ve had a box office success that weekend or you can have a cult movie people are obsessed with, and I’ll definitely take the cult movie option. We still keep talking about wanting to do a Dewey Cox concert tour.

Jack White also cameos as Elvis. You mentioned earlier, ginning up the courage to record yourself. You did some songs with Jack a few years after Walk Hard, too.

REILLY: That was with the bluegrass band, I did a few 45s for Jack’s label. He did drum on one song. We recorded at his house. We felt incredibly lucky. We hadn’t recorded anything with that band yet and it was a dream to get down there and work with him.

I met Jack before Walk Hard. I heard he was doing “Mister Cellophane” in concert with the White Stripes. I went and saw it, I think they were doing it as an encore. We hit it off. We have similar pasts — both grew up Catholic in big Irish families, he’s from Detroit and I’m from Chicago. We’re still very close friends. I was just working with him on something recently that’s going to be a big splash, I think.

The reason I asked him to be Elvis is I feel Jack is the last rockstar, in a way. When you see him in concert it’s like seeing Jimi Hendrix or something. There’s just not many people that can do that. I felt if anyone was anywhere near Elvis these days, it’s Jack White.

“Boats ‘N Hoes” In Step Brothers (2008), Rapping “Boats ‘N Hoes” And “Gin And Juice” With Snoop Dogg And Will Ferrell (2023)

You’ve also had a lot of rap moments in your career.

REILLY:“Boats ‘N Hoes.”

Of course. You also appear on an A$AP Mob mixtape. I was even watching your “freestyle” over Kanye and Common’s “Southside” on Sway.

REILLY: I was just doing this Sugarhill record I had when I was 12 or 13. I was really into hip-hop and funk when I was that age. I would listen to the vinyl and take a cassette recorder and hold a microphone up to the speaker and transcribe lyric by lyric. Then I memorized that whole song.

I found this video of you and Will Ferrell rapping “Boats ‘N Hoes” with Snoop Dogg, as well as “Gin And Juice.”

REILLY: That was for Will’s benefit, Cancer For College charity. He asked Snoop. I think they already knew each other. He already had a nickname for Will; he was like, “What’s up Baby Boy?” When he walked up for rehearsal, right before we did it he goes, “I fuck with both y’all.” I was like, “Damn! That’s so cool.” He really carries himself in this beautiful, elegant way — he’s such a cool guy, he’s so friendly. Rappers seem to love me. Rappers and surfers. I don’t know why that is. [Laughs.]

So did you and Will have to rehearse “Gin And Juice” with Snoop?

REILLY: I can’t speak for Will, but I know that song top to bottom already. For the amount that Snoop smokes, it’s really impressive he can remember all those words. It’s almost like a superpower. How do you do that? If I had even a puff of weed all the words would immediately go out of my head.

Playing An Older Mike D In Beastie Boys’ “Make Some Noise” (2011), Miming Leon Michels’ Saxophone Part In Molly Lewis’ “Oceanic Feeling” (2021), Performing As Jon Spencer Blues Explosion In “Talk About The Blues” (1998)

You mentioned John Reilly & Friends or Mister Romantic as you really creating your own space for music. I’d noticed this funny mini-thread where you’ve been in several music videos where you’re pretending to be another musician. It goes all the way back to Jon Spencer Blues Explosion’s “Talk About The Blues,” where you and Giovanni Ribisi and Winona Ryder perform as the band. You also stand in for Leon Michels and do a sax part while dressed as a king in Molly Lewis’ “Oceanic Feeling” video —

REILLY: I don’t remember half this stuff, this is amazing.

I have my ways. But every now and then the internet lies to you — I did one of these with Bonnie Raitt where we ran into something where she was like “I don’t think that actually happened.”

REILLY: She’s another one who loves Walk Hard! I was on A Prairie Home Companion with her once and standing backstage with her. She didn’t know I was there and turned around like, “Dewey Cox! Oh my god, me and my band are obsessed.” She’s always been a hero of mine too.

One of the other videos was Beastie Boys’ “Make Some Noise” in 2011.

REILLY: I was good friends with all three of those guys. I’m probably closest with Mike D. That was just a friend gig.

There were so many different actors in that video.

REILLY: I think it was all shot in one day. It was the only piss fight I’ve ever done. [Laughs.] Sometimes when you do this job every once in a while you find yourself like, “What am I doing? This is my day, I’m peeing at other people while they pee at me.” It’s really absurd. I’m good friends with Jack Black, too, and we were just laughing ourselves silly that day.

Did it feel different when you were in the Jon Spencer video? You were established by then, but not so involved in music publicly.

REILLY: I think that was also a friend thing. Actually, Mike Diamond knew those guys, and they thought I looked a bit like Russell [Simins]. I was a fan of the band, too, but it was just kind of random I was the right height.

Singing The Human League’s “Don’t You Want Me” In Cyrus (2010)

My editor wanted me to ask you about this one. It’s one of those sad-funny scenes that turns poignant.

REILLY: This was hard. In the movie, all the sudden I start singing to the whole party and it’s this cringe-y moment for the character. But as an actor — the room was full of people I didn’t know, all these extras standing around, so it was totally cringe-y for me too. I couldn’t believe I had to do this in front of all these people. That song is such an earworm. If you even think about that song all the sudden you’re running through it in your head.

Another ‘80s thing you called back to was Wreck-It Ralph singing “Never Gonna Give You Up,” which is obviously a meme. I know the Stones were huge for you when you were a kid in the ’80s, but do you have any attachment to those big ’80s hits or synth-pop?

REILLY: Oh, sure. But yeah the Stones… People in my neighborhood were calling me Mick for a while because all I was listening to was the Stones. Some Girls, that’s the record I really liked. I really liked disco as a younger kid when I was growing up in Chicago, in the South Side. I used to dance in the kitchen. Then all the sudden it became uncool. “Disco sucks!” Some part of me was like, “I wish it was cool to dance again”. I think that whole movement was started by guys who couldn’t dance. [Laughs.] When I heard Some Girls, that was the Stones acknowledging disco was cool, and it made rock ‘n’ roll sexy and danceable again. It was life-affirming that the Stones did that.

Singing Aimee Mann’s “Wise Up” In Magnolia (1999), Cameo In Fiona Apple’s “Across The Universe” (1998)

There’s this moment towards the end of Magnolia where the reality of the film breaks a bit, and each of you are singing part of Aimee Man’s “Wise Up.” Do you remember how Paul presented or prepped you guys for this idea?

REILLY: It was in the script. I’m friends with Aimee, and I was very close with her and Michael Penn back then. It was all part of the crew. We were all obsessed with Aimee’s music already. It wasn’t such a departure to me. Paul said we’d each sing a part of this. It wasn’t confusing.

How did you feel when you first saw the sequence finished in the movie?

REILLY: It was so effective. The song wasn’t written for the movie, but it somehow encapsulates what a lot of the characters are feeling in that movie. I wish I could remember what it felt like to see Magnolia the first time. It’s obviously such a big part of my life. That character was based on some improvisations I did when Paul and I were making these cops videos. They almost feel like family memories to me as opposed to a work memory. I think Paul also shot the video for Aimee’s “One” at the same time as we were making that video.

Funnily enough the next thing I was going to ask was about you being in Fiona Apple’s “Across The Universe” video, which was directed by Paul.

REILLY: That was a little Easter Egg. A run-on part as it were.

He just asked you to ransack this soda shop?

REILLY: We were super close — Paul and I still are. Someone like Paul asks me to do something, I’ll do anything. I’ll come be Herman Munster for a day. [Reilly is referring to his uncredited cameo in Anderson’s most recent film, Licorice Pizza —Ed.] He’s one of my best friends, and I think he’s the greatest living director in the world right now. Why wouldn’t you say yes? It’s not like he asks me to do stupid shit. It’s always an inspired choice, and he always picks you for a reason. I was hanging around with Paul and Fiona a lot at that point. I was probably going to visit the set anyway, so why not?

Let’s go back to Aimee Mann for a second. Nine or 10 years later, you were also in her Christmas Carol spoof as the Ghost Of Christmas Future.

REILLY: Was I? We filmed that?

It’s on YouTube.

REILLY: I remember touring with Aimee’s Christmas show. We went on the road with her. I guess I’ll have to look that one up. [Laughs.]

[Laughs.] Maybe we’ll have to skip that one if it’s lost to the archives.

REILLY: I’ve had a busy life.

The Studio Sequence And “Sister Christian” Scene In Boogie Nights (1997)

When you talk about hanging with Fiona, or playing at Largo, this is what you were talking about with music in the ’90s? You’d just sit in and jam with people around town?

REILLY: I think the first bit of music I did in a movie was in Days Of Thunder, actually. I’m sitting there noodling on the guitar. I’m not sure if the sound ended up being my actual guitar-playing or dubbed it in later.

You do that again in the ’80s studio sequences in Boogie Nights.

REILLY: “You got the touch!” Yeah. It’s really the cocaine section of that movie. [Laughs.] The characters get deep into the snow there. All that stuff in the recording studio was improvised. Paul would have sections in the script that would say, “Now the guys try to get the tapes back from the studio.” All that stuff, like when I’m going, “Nick, he says he wants more bass!” I think Michael [Penn] was so freaked out by the end of that because he didn’t know what was coming out of these characters, they’re so insane. There’s a whole section on the DVD called the John C. Reilly Files that was all crazy improv takes we did.

What about the song you’re sitting there writing?

REILLY: Paul wrote the lyrics to it, and I wrote the music the night before. So we weren’t improvising there. I still get tiny amounts of money for that song. I’ll get a check from BMI for like 18 cents from “Feel The Heat.” But, it is on the soundtrack, you know?

Boogie Nights also has the infamous “Sister Christian” scene. Sometimes you read interviews with people where they’re like, “We didn’t know it was going to be that song.”

REILLY: No, no. Any good director knows to figure that out beforehand. You can always spot it in movies when people are not quite dancing to the right beat. Paul completely designed everything that’s in that movie. All the music was figured out ahead of time, including the music that plays during my magic act.

What you might not know was that room was rigged with something like a thousand squibs. It’s the bullet hits they put on the wall to look like something’s been shot. In the movie we run out and he follows and shoots at the car and that’s the end of that scene. But what happened in the script, and what we filmed, is we run outside, he shoots at us, and he goes back inside and gets an M-16 and then cops arrive as it switches from “Sister Christian” to “99 Luftballons,” and the cops perforate the house with gunfire. It was almost a Scarface moment.

Filming that scene had this crazy powder-keg feeling because the guy is lighting off real firecrackers, and you never quite know when they’re going to go off, so all our reactions are very real. But also, we’ve been warned over and over, “Don’t touch the walls, don’t do this, don’t do that,” because the whole place is rigged with gunpowder. [Laughs.] It gave it this really edgy feeling from the beginning.

Mister Romantic is out today via Eternal Magic.