As The Late Show with Stephen Colbert heads into its final stretch, there are plenty of ways to take stock of what made the show special. Chief among them: the sharp monologues and insightful interviews that came to define it. But one of Colbert’s most unsung talents has been hiding in plain sight since the very start—his voice.
Long before he took over the Ed Sullivan Theater, Colbert’s musical instincts were part of his comedy DNA, whether on Strangers with Candy, The Colbert Report, or even earlier on the Chicago stage. At The Late Show, that musicality found a bigger playground—and over the years, it became a recurring delight. Sometimes he stepped into a guest’s world, holding his own alongside major recording artists in surprisingly polished duets. Other times, he leaned into the absurd, teaming up with guests (especially those with a Broadway pedigree) for musical comedy numbers that were as silly as they were technically impressive.
What sets Stephen Colbert apart isn’t just his willingness to sing—it’s the commitment. He doesn’t half-do a song. Whether he’s harmonizing with a pro or belting out a joke premise with full theatrical gusto, Colbert brings precision, confidence, and, yes, a genuinely strong set of pipes.
Looking back, these musical moments form their own highlight reel—one that cuts across formats, musical genres, and tones, but always lands in the same place: a host who seems to be having the time of his life, and inviting the audience along with him. Here are some of our favorites.
Me and Julio Down by the Schoolyard (with Paul Simon)
Paul Simon’s appearance on The Late Show a few weeks back was a fitting bookend to a decade-long relationship that dates back to Colbert’s first week at CBS, when a deadpan Simon played the leader of a Paul Simon tribute band named “Troubled Waters.” The fake band’s appearance gave Colbert the chance to fulfill a dream of performing the whistle solo in “Me and Julio Down by the Schoolyard.” See also: Colbert helps Paul Simon rewrite “The 59th Street Bridge Song (Feeling Groovy)”
Wouldn’t It Be Loverly? (with Matthew Broderick)
As late-night’s premier promoter of musical theater, Colbert performed quite a few Broadway-inspired duets. In a January 2016 appearance, stage veteran Matthew Broderick confessed he’d never been given a chance to indulge his inner Eliza Doolittle, leading both men to take the stage for an “impromptu” homage to My Fair Lady, complete with street urchins tossing rose petals at the duo. See also: Sondheim’s “Side by Side” (with Christine Baranski) and “Matchmaker, Matchmaker”/”Tradition” (with the cast of Broadway’s Fiddler on the Roof).
Anything Can Be a Musical (with Rachel Bloom)
Hot off her 2016 Golden Globes win for Crazy Ex-Girlfriend, song and dance woman Rachel Bloom joined Colbert for an original number about how “Anything Can Be a Musical.” To prove their point, the two performers found a way to plug TV shows on the CW in song.
Button! (with Lin-Manuel Miranda)
For sheer chutzpah, it’s hard to beat Colbert’s pairing with Lin-Manuel Miranda, in which the duo stage a hip-hop musical about little-known Founding Father Button Gwinnett. Sure, Colbert sputters a few of his Hamilton-style rhymes, but “Button!” was about as ambitious as live-to-tape late-night talk shows get.
Fire and Rain (with James Taylor)
Colbert’s duets weren’t all about showing off The Late Show host’s impressive singing voice. His musical guests also got to flex their comedy skills. Check out James Taylor cracking himself up as he describes all the things he’s seen beyond “Fire and Rain.” Taylor’s struggle to keep a straight face is part of the charm. See also: “Good Riddance”-Affordable Lyrics Edition (with Green Day) and “You Can Close Your Eyes” (with James Taylor), in which the duo plays it straight.
Mockingbird (with Carly Simon)
Speaking of James Taylor, Colbert stepped into the mellow troubadour’s shoes himself one night in 2015 when Carly Simon visited The Late Show and agreed to reprise her and Taylor’s 1973 cover of “Mockingbird” with the host.
Me and My Shadow (with James Corden)
When it comes to late-night hosts with musical theater bona fides, James Corden—whose Late Late Show followed Colbert’s Late Show for seven and a half seasons—was in a league of his own. Naturally, the two couldn’t resist leaning into that shared sensibility when Corden visited in October 2015.
What followed was a knowing wink at their back-to-back perch on CBS’s late-night lineup. With plenty of hand-holding, soft-shoe choreography, and playfully theatrical delivery, Colbert and Corden leaned into the idea that one host inevitably trails the other—whether he likes it or not. The result was equal parts Rat Pack homage and network synergy.
That’s the Way That the World Goes ’Round (with John Prine)
When John Prine first appeared on Colbert’s Late Show in 2016, the two teamed up for a duet of Prine’s 1978 classic that was originally released as a web exclusive. At the top of the performance, Colbert—a longtime Prine fan—noted it would be released online “unless something terrible happens and we have to cheer up the world on the TV show.”
Three and a half years later, that offhand line took on unexpected weight. As Prine battled COVID in the early days of the pandemic, Colbert brought the performance to air for the first time, calling it one of the happiest moments he’d experienced on the show. Prine died a week later.
(You Make Me Feel Like) A Natural Woman (with Jennifer Hudson)
When Jennifer Hudson stopped by The Late Show in 2021 to promote her Aretha Franklin biopic Respect, she turned the interview into a masterclass—pulling Colbert and bandleader Jon Batiste into a performance of “(You Make Me Feel Like) A Natural Woman.” Seated at the piano, Hudson demonstrated the difference between her own voice and Franklin’s, explaining that Aretha sang “from the top of her head,” while Hudson’s voice comes “from her feet.”
After toggling between the two styles verse by verse, Hudson brought Batiste and Colbert in for the chorus, where a falsetto Colbert gamely climbed into Hudson’s stratosphere and somehow stuck the landing—earning genuine surprise (and approval) from Hudson.
I’ll Make Love to You (But We Don’t Have To) (with Boyz II Men)
When one thinks of funny musical acts, ’90s vocal harmony group Boyz II Men doesn’t immediately come to mind—which makes it all the funnier when they croon about their weary wives being too tired for sex. The song, “I’ll Make Love to You (But We Don’t Have To),” also features one of Colbert’s best vocal performances, channeling his inner Color Me Badd. See also: “It’s the End of the Year As We Know It” (with Michael Stipe).
A Song About Friendship (with Steve Martin)
But if you’re strictly looking for laughs, old reliable Steve Martin delivers. Even Colbert can’t keep a straight face as Martin plucks his banjo in tribute to his best pal, Stephen … er, Gary.
Feel Good Inc. (with Gorillaz)
When Gorillaz stopped by The Ed Sullivan Theater in 2017 amid the rollout of Humanz, their on-air performance stuck to newer material—but an online bonus clip gave Colbert a chance to jump into one of the band’s biggest hits. Stepping in for De La Soul on “Feel Good Inc.,” Colbert appeared on a video screen behind the band, decked out in a fur hood resembling the one from the original music video.
What followed was a committed (if slightly tongue-in-cheek) turn at the mic, with Colbert gamely tackling the rap verses—subbing in a few of his own TV-friendly tweaks along the way. He may not have the flow of a seasoned hip-hop act, but he more than held his own to the delight of the crowd.
Carol of the Bells (with Henry Rollins)
For those who prefer to rock out, Henry Rollins gave Colbert permission to scream. Bang your head, and while you’re at it, make Rollins’ version of this Christmas classic a holiday standard. See also: “Christmas is Now” (with Norah Jones).
My Kind of America (with Jack Black)
In another of Colbert’s very early Late Show musical bits, the host teamed up with Jack Black to solve a very specific political problem: what happens when candidates can’t get permission to use actual hit songs on the campaign trail? Their answer was “My Kind of America,” a deliberately catch-all anthem designed to be just vague—and just catchy—enough to work for anyone.
What followed was a full-throttle comedy number, with Black bursting onstage in full denim to join Colbert for a rapid-fire rundown of all things vaguely patriotic, from pop culture touchstones to snack foods. Complete with backup dancers, and an over-the-top vocal finish, the performance walked the line between parody and genuine showstopper.
This Year (with The Mountain Goats)
None of Colbert’s musical collaborations have taken on a second life quite like this one. Originally performed in 2019, his onstage team-up with The Mountain Goats resurfaced last summer shortly after news broke that CBS had canceled The Late Show, giving Colbert nine months to, as he put it, “land this plane perfectly” while continuing his nightly focus on Donald Trump and the state of the country.
The context gave added weight to a performance that already meant something to Colbert. Introducing the song at the time, he noted it wasn’t from the band’s current album—he’d simply requested it because it was a personal favorite. About 90 seconds in, Colbert joins John Darnielle for the chorus—“I am going to make it through this year if it kills me”—and never leaves, turning the number into a full-throated duet. What once played as a joyful, slightly unhinged singalong now lands as something more: a defiant anthem that, like Colbert himself, refuses to go quietly.
Rockin’ in the Free World (with Pearl Jam)
If we had to pick one Colbert duet for him to go out on, it would be this—a suitably defiant anthem that pairs the host with one of America’s great rock bands. When Pearl Jam stopped by The Late Show in 2015, they tore through “Mind Your Manners” before keeping the energy up for a cover of Neil Young’s “Rockin’ in the Free World,” with Colbert jumping in on vocals.
It’s the kind of full-throated, slightly ragged singalong that plays to all of Colbert’s strengths as a performer. And in the years since, Young’s song has only grown more pointed as a protest staple, making the performance feel newly resonant in hindsight. If “This Year” is Colbert’s endurance mantra, this is his rallying cry.
The Late Show with Stephen Colbert returns with the first of its final twelve episodes tonight. The show airs its series finale Thursday, May 21, 2026.
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