If the great songwriters of America all rose from the dead (or wandered over from Bob Dylan’s house) and had a family reunion, John Prine and Jimmy Buffett would be the two weird uncles holding court at opposite ends of the picnic table. One would be fingerpicking his way through a story about a mail-order bride, the other sipping something rum-based and preaching the gospel of flip-flops.

Their music may have landed in different sections of the record store, but both built loyal followings by writing songs that were funny, unpretentious and thoroughly human.

Though they never released an album together, Prine and Buffett were friends, contemporaries and kindred spirits in the alt-country universe. Buffett even released music on Prine’s independent label, Oh Boy Records. And on the cover of Steve Goodman’s 1972 album “Somebody Else’s Troubles,” you’ll spot them side by side at a bar — two artists not yet legends, just guys with guitars and something to say.

“They were goofy outsiders to country music, and always true to themselves,” said Boulder musician Bob Barrick. “Fans of both these guys thrive on authenticity.”

That spirit of authenticity — and a shared love for two of America’s most beloved songwriters — takes center stage at 8 p.m. Friday at the Fox Theatre, 1135 13th St., Boulder. Presented by The Colorado Sound, the double-bill tribute features Jammy Buffet, Barrick’s joyful deep dive into Jimmy Buffett’s catalog, and Illegal Smile, a heartfelt homage to John Prine, led by Boulder musician Derek Dames Ohl. Rounding out the lineup is Denver-based trio Something Slight, whose genre-bending blend of folk, country and Americana sets the tone for an evening of storytelling, nostalgia and sing-alongs.

Tickets are available at z2ent.com.

For Ohl, the Prine tribute isn’t just a one-off — it’s a full-circle moment. The Boulder-born-and-raised singer-songwriter has been weaving Prine’s songs into his sets for years, even during his time with local band Flash Mountain Flood.

“Since I started chasing the crazy dream of being a musician, my sets have been chock-full of Prine tunes,” Ohl said. “Flash Mountain Flood used to play a 20-minute rendition of ‘Angel From Montgomery’ 10 years ago. Anyone who knows me knows I’m a bit obsessed.”

Illegal Smile was born from that obsession — and from a desire to keep Prine’s spirit alive on Colorado stages. The band name, lifted from one of Prine’s earliest hits, captures the late songwriter’s signature blend of mischief and melancholy. And while Ohl fronts the project, it’s very much a community effort, featuring a rotating cast of Front Range musicians (think Flash Mountain Flood, Liver Down the River, Mighty Holler) hopping in for what often turns into a full-on musical circus.

“The band is practically an all-star circus of local musicians from bands you know,” Ohl said.

While the loss of Prine in 2020 at age 73 still stings, Ohl said playing his songs on stage is a way of processing that grief — and inviting others to do the same.

“The hardest part of COVID for me was losing John Prine,” he said. “Now more than ever, I believe people could truly appreciate his catalog, and I’m overjoyed to sing his songs on stage with all my friends.”

Prine’s influence also runs deep in Ohl’s songwriting, which is made up of equal parts wry humor and unvarnished honesty.

“I take a lot of influence from John, and think that most modern songwriters do,” he said. “The art of taking control of a room full of people, with just a guitar and your words, is very special in my book. I truly wonder if this is the path I’d be on if it weren’t for Prine proving it’s possible for anyone to make a living and travel the world with music. Blows my mind to this day.”

If Prine himself were around to catch the show, Ohl suspects he might jump in on “Crooked Piece of Time” — a bittersweet tune that captures the songwriter’s trademark existential shrug.

Meanwhile, Jammy Buffet reimagines Buffett’s catalog for a new generation of Parrotheads, psych-rock lovers, and anyone who’s ever longed to disappear to a beach with no cell service.

“The Jammy Buffet show is, at its core, a party,” Barrick said. “I grew up in Indiana going to Jimmy’s shows at Deer Creek Music Center, and they left an impression. We’re bringing that equal parts hedonistic and romantic energy that Buffett fans know and love into a new generation.”

That energy includes the hits, but Barrick and crew also dig deep into Buffett’s Key West-era catalog, those poetic, slightly weirder tunes that reveal the songwriter beneath the Hawaiian shirt.

“I don’t want to give too much away,” Barrick said, “but our calling card is new arrangements on old classics. ‘Come Monday’ and ‘Son of a Son of a Sailor’ will catch people pleasantly surprised. I’m a mega-fan, myself, so we sprinkle in deep cuts — ‘Woman Goin’ Crazy on Caroline Street,’ ‘Tampico Trauma’—tunes like that.” (From 1976, 1977 respectively.)

The goal, Barrick said, isn’t just to throw a tropical rager (though that’s very much on the table). It’s to share what makes Buffett’s songs tick — sneaky optimism, defiance of seriousness and ability to remind listeners that escapism and emotional truth don’t have to be mutually exclusive.

“I hope folks come away from our show feeling the unencumbered optimism that Jimmy’s songs always give me,” he said.

At first glance, pairing tributes to John Prine and Jimmy Buffett might seem like an oddball move. But for Barrick and Ohl — who have been sharing stages and swapping musical ideas for years — it’s a natural fit. Friday’s show will feature more than a few familiar faces pulling double duty in both Illegal Smile and Jammy Buffet, paving the way for spontaneous crossovers and extended jams.

“We’ve got some tricks up our sleeves,” Ohl said. “Whether you’re wasting away in Margaritaville or fishin’ and whistlin’, it’s safe to say you’re going to have a great time at the Fox.”

Before the Buffett bops and Prine poetry kick off, Denver-based trio Something Slight will warm up the stage with its signature blend of Americana, folk and country. Known for tightly crafted originals and a willingness to push the edges of genres, the band adds just the right dose of fresh energy to an already stacked lineup. It’s roots music with a twist — grounded, playful and right at home in a night full of tributes to musical misfits.

From barefoot ballads to tropical tailspins, Illegal Smile and Jammy Buffet promise a tribute night that’s less buttoned-up memorial, more joyful celebration.

Expect nostalgia. Expect sing-alongs. Expect at least one guy in a Hawaiian shirt yelling “Salt!” at full volume. With two tribute sets that tap into the heart, humor and humanity of American songwriting, the night promises a little something for everyone — plus a few heartfelt tears between the toe-taps.

Doors open at 7 p.m., music starts at 8. All ages are welcome (those under 16 years old must be accompanied by an adult).