Stephen Colbert is preparing for life after late night — and his next chapter begins not at a desk, but on a crime dramedy. The Late Show host, who will depart his CBS perch when the program ends in May 2026, will guest star in the season 3 premiere of Elsbeth on Oct. 12. For Colbert, the role is both a return to his acting roots and a poignant milestone. But he’s already admitted one aspect of the job was “truly upsetting.”

Colbert Plays Scotty Bristol

In his guest spot, Colbert portrays Scotty Bristol, a fictional late-night host who feels like a playful mirror of Colbert himself. His sidekick is portrayed by Andy Richter, best known for his decades alongside Conan O’Brien. And in a stroke of comedic synergy, Colbert is also joined by longtime collaborator Amy Sedaris, playing Bristol’s head writer.

The setup promises meta comedy: a real late-night icon playing a fictional late-night host on a network drama. But according to Colbert, the experience quickly veered into uncomfortable territory.

The “Truly Upsetting” Seduction

During an interview with Elsbeth star Carrie Preston, Colbert confessed that one storyline was difficult to play out.

“The hardest part for me is that at one point Amy Sedaris, who I have known since I was 24, she’s like my sister. She seduces me at one point. That was truly upsetting.”

For Colbert, the scripted seduction clashed with decades of real-world friendship. He and Sedaris first met in Chicago’s improv scene in the 1980s and quickly developed a sibling-like bond. After more than 35 years of collaborations — from Comedy Central’s Exit 57 to Strangers with Candy — pretending to be romantically entangled on screen was, understandably, awkward.

Still, the moment underscores what Colbert and Sedaris have always embraced: comedy built on the unexpected, even when it makes them (and the audience) squirm.

A Timely Pivot

Colbert’s decision to film Elsbeth came just days after CBS announced that The Late Show would end in May 2026. Rather than retreat, he leaned into a new opportunity, reminding fans that his career extends beyond monologues and interviews.

The timing makes his cameo feel symbolic. Colbert is not fading quietly from the spotlight; he’s testing new waters in scripted television. And for audiences who know him primarily as a satirist, seeing him act again will be a reminder of the skills that launched his career long before The Colbert Report.

Colbert the Actor: A Career Before the Desk

Though best known today as a talk-show host, Colbert spent decades as a working actor and comedian. His Elsbeth cameo is less a departure than a return to form.

Second City Roots: Colbert cut his teeth in Chicago’s famed Second City improv troupe, where he met collaborators like Sedaris and Paul Dinello.

Exit 57 (1995–96): This short-lived Comedy Central sketch show starred Colbert, Sedaris, and Dinello. Though it lasted just one season, it showcased Colbert’s range and offbeat humor.

Strangers with Candy (1999–2000): Colbert played Chuck Noblet, a closeted high-school teacher in Sedaris’s cult comedy series. His dry delivery and absurdity made him a standout.

The Daily Show (1997–2005): Colbert’s big break came as a correspondent, where his “straight man” satire set the stage for his later persona.

The Colbert Report (2005–2014): For nine years, Colbert played a bombastic conservative pundit — arguably one of the most sustained pieces of performance art in TV history. The role earned him critical acclaim, Emmys, and a devoted audience.

With Elsbeth, Colbert is circling back to scripted performance, though this time as himself-with-a-twist.

Why Elsbeth?

On paper, the match makes sense. Elsbeth, a spinoff of The Good Wife and The Good Fight, thrives on quirky, meta storytelling. Casting Colbert as a fictional late-night host is both cheeky and in line with the show’s offbeat tone.

For CBS, it’s also savvy synergy: spotlighting one of its biggest stars in a different format while The Late Show winds down. For Colbert, it’s a way to experiment — dipping back into acting without the commitment of a series.

A Full-Circle Reunion With Sedaris

Perhaps the most significant element of Colbert’s appearance is his reunion with Amy Sedaris. Their partnership spans nearly four decades, rooted in Chicago’s comedy underground and flourishing on stage and screen.

Exit 57: Their first major TV collaboration.

Strangers with Candy: Their cult hit, cementing their comedic chemistry.

Guest Spots: Sedaris has appeared on Colbert’s shows, while Colbert has praised her fearless comedy in countless interviews.

For fans, seeing them together again — even in a “truly upsetting” scenario — is a nostalgic nod to their shared history.

What It Suggests About Colbert’s Future

Colbert has been candid about life after late night. At 60, he’s hinted at scaling back but hasn’t ruled out scripted work, producing, or even returning to voice acting (he voiced Ace in Harvey Birdman, Attorney at Law).

His Elsbeth cameo hints at a future where Colbert dips in and out of acting, leveraging his comedic instincts in one-off roles. It also shows his willingness to surprise audiences — rather than clinging to the Colbert persona, he’s comfortable reinventing himself.

Given the success of other late-night alumni who pivoted (Jon Stewart with The Problem, Conan O’Brien with travelogues and podcasts), Colbert’s future may be just as varied.

What Fans Can Expect in the Premiere

When the Elsbeth season 3 premiere airs Oct. 12, viewers can anticipate:

Meta Comedy: Colbert playing a late-night host — not far from reality, but with scripted quirks.

Discomfort for Laughs: Sedaris’s seduction storyline promises both cringe and comedy.

Rich Guest Cast: With Andy Richter as the sidekick, the episode doubles as a mini late-night reunion.

Cultural Context: Coming months after the announcement of The Late Show’s end, the role feels like a statement about Colbert’s resilience and range.

Conclusion: A Step Into the Future

Stephen Colbert’s guest role on Elsbeth is more than a one-off cameo. It’s a reunion with his oldest collaborator, a reminder of his roots as an actor, and a signal that his post-Late Show career may be just as eclectic as the one that brought him here.

Yes, Amy Sedaris’s scripted seduction may have been “truly upsetting.” But for Colbert, it’s proof that after decades behind a desk, he’s still willing to put himself in uncomfortable, unexpected situations — all in service of comedy.

As he prepares to leave late night, Elsbeth offers a glimpse of what’s next: Colbert, the performer, reminding us that satire was only one act in a much larger career.