Actor John C. Reilly Brings “Mister Romantic” To The Country-Folk World With Sierra Ferrell

Your favorite Step Brothers legend is trading in the drums for a microphone.

John C. Reilly, the same actor who brought legendary characters like Dale Doback, Cal Naughton Jr., and of course, Dewey Cox to life, is stepping into a new role. But this time, he’s not playing a character in a comedy. He’s performing under a new musical persona: Mister Romantic.

And he’s not just dabbling. Reilly has quietly been carving out a name for himself in the folk and Americana space, blending his lifelong passion for music with a fresh creative chapter.

Singing With Sierra Ferrell at Lollapalooza

In one of his latest surprise appearances, Mister Romantic joined none other than Sierra Ferrell, one of country’s most beloved rising stars, for a stripped-down, a cappella performance during the opening of Lollapalooza in Chicago.

The unexpected duo delivered a raw, melodic moment that had fans doing a double take.

Watch the performance here:

@lifewithavr DALE?!?!? Is that you?!?!? INSANE way to kick off Lollapalooza 2025!!! @Sierra Ferrell is INCREDIBLE #catalinawinemixer #johncreilly #sierraferrell #countrymusic #countrymusicconcert #concert ♬ original sound – Arden

Another angle:

@fabuloussofie At first I thought it was Bill Murray, but no it’s only John C Reilly. Amazing! #sierraferrell #johncreilly #lollapalooza #concert @Sierra Ferrell @metrochicago @Lollapalooza USA ♬ original sound – Sofie.Cassin

If Dale Doback told us one day he’d be singing folk music with Sierra Ferrell, we probably would’ve never believed him.

Turns out, he wasn’t joking, and it wasn’t Brennan who’s “voice is like a combination of Fergie and Jesus,” it was Dale’s.

While the Sierra Ferrell feature has shocked fans, it’s not the first time Mister Romantic has turned up in the music world. Reilly recently appeared at the Newport Folk Festival, performing Bob Dylan’s “Maggie’s Farm” alongside Margo Price and Jesse Welles. Another unexpected collaboration that just worked.

Watch the Newport performance:

It doesn’t stop there. Reilly was recently announced as the keynote speaker at this year’s AmericanaFest in Nashville, further cementing his place within the broader Americana community. What began as a side project is quickly becoming something much more rooted and respected.

Debut Album: What’s Not to Love?

With all the buzz, Mister Romantic recently dropped his debut album, What’s Not to Love?, a collection of timeless classics including covers of “La Vie En Rose” by Edith Piaf and “Moonlight Serenade” by Glenn Miller.

It’s not your typical country record, but it leans into the romantic, old-world spirit that lingers around traditional folk, jazz, and Americana influences.

Upcoming Tour Dates

Mister Romantic is also hitting the road, with shows scheduled in California, London, and Reilly’s hometown of Chicago:

October 10 – Los Angeles, CA @ The Palace Theatre

October 13 – Livermore, CA @ Livermore Valley Arts

November 18 – London, UK @ Soho Theatre Walthamstow (Sold Out)

November 19 – London, UK @ Soho Theatre Walthamstow

December 4 – Chicago, IL @ The Downstairs Theatre at Steppenwolf

December 5 – Chicago, IL @ The Downstairs Theatre at Steppenwolf

December 6 – Chicago, IL @ The Downstairs Theatre at Steppenwolf

John C. Reilly has always been full of surprises. And this chapter feels personal, honest, and straight from the heart. Mister Romantic might be new to us, but it’s clear he’s been in the making for a long time.The post Actor John C. Reilly Brings “Mister Romantic” To The Country-Folk World With Sierra Ferrell first appeared on Whiskey Riff.