Stephen Colbert (Communication ’86) has long gravitated toward what one of his friends called “playful danger.”

He leaned into this instinct for the past decade on CBS’ “The Late Show with Stephen Colbert,” which he recently announced would go off the air in May 2026. Colbert catapulted the late-night talk show to the top of its timeslot’s ratings and became known for regularly roasting President Donald Trump.

Colbert has reveled in the president singling him out. When Trump first dismissed him as a “no-talent guy” in 2017, the host pressed his fingertips together and cackled. When Trump did it again a year later, Colbert called out the president for not saying his name.

On July 18, the morning after the show’s cancellation was announced, Trump lobbed a similar insult his way.

“I absolutely love that Colbert’ got fired,” the president wrote on Truth Social. “His talent was even less than his ratings.”

This time, network TV’s top-rated late-night host lifted a finger in the air, raised his voice and asked, “Would an untalented man be able to compose the following satirical witticism?” He then turned to a camera labeled “Eloquence Cam” and said, with lower volume and a more curt tone, “Go f–k yourself.”

Anne Libera (Communication ’86), Colbert’s former classmate and roommate turned close friend, said moments like these reflect Colbert’s love of “playful danger” and the audacity to “take a chance and to see what happens.”

“He’s really willing to say, ‘What happens if I just do this, and/or what happens if I let go and speak from my heart?’” Libera said.

Colbert’s sharp wits and compassion have driven his decades-long comedy career, according to several peers and one professor who saw him display those traits at Northwestern. His show’s abrupt cancellation signals an uncertain future for late-night television and political comedy as a whole, but Colbert maintains the final word on his path forward.

Intelligent ‘enthusiast,’ meet ‘high-status idiot’

For more than a decade, Colbert satirized conservative cable news hosts by pretending to be one of them. He called his character, who shared his name, a “well-intentioned, poorly informed, high-status idiot.”

But before Colbert played “high-status idiots” on TV, he played a similar character at least once at NU.

As a senior in the play “Terry Won’t Talk,” Colbert chomped on a cigar and donned a blue blazer with gold buttons to play a manipulative high school principal. The production’s director, Aaron Posner (Communication ’86), said Colbert’s character resembled the conservative pundit he would eventually play on two Comedy Central programs: “The Daily Show,” where he served as a correspondent from 1997 to 2005, and “The Colbert Report,” which he hosted in character from 2005 to 2014.

The production “was sort of metatheatrical, and it was very playful, and it was building off of who the actual people were,” Posner said.

Posner called the real Colbert an “enthusiast,” evident in both “The Colbert Report” and “The Late Show.” Colbert shed his conservative alter ego when he moved to CBS, swapping ironic satire with broader jokes and more sincere interviews. His fictional equivalent remained in an unhappy marriage, but the real Colbert brightens up smiling whenever his wife, Evie, makes recurring appearances on “The Late Show.”

Posner said the comedian could get away with playing “idiot” and “a–hole” characters because he’s smarter and kinder in real life.

“What has allowed him to be such a brilliant talk show host is that he’s actually interested in things and in people and in the world,” Posner said.

Several peers said Colbert combined his inquisitiveness with a sharp memory to discuss topics he found interesting at length. Ayun Halliday (Communication ’87) — who dated Colbert in college and now writes and acts in New York City — said her then-boyfriend would sometimes engage in extended conversations at parties on arcane topics like the fourth dimension.

According to Libera, Colbert displayed an especially profound “love of language,” and he understood how people manipulate it for their own purposes. She cited his debut “Colbert Report” episode in October 2005, during which the fictional Colbert pontificated about an invented word: “truthiness.” In character, Colbert decried the divide between “those who think with their head and those who know with their heart,” proclaiming the truth comes not from books but from the gut.

The American Dialect Society and Merriam-Webster declared “truthiness” the word of the year in 2005 and 2006, respectively.

After Trump’s first election in 2016, Oxford named a similar word of the year: “post-truth,” referring to times when “objective facts are less influential in shaping public opinion than appeals to emotion and personal belief.”

Colbert jokingly lamented on “The Late Show” that “post-truth” ripped off “truthiness.”

A new era of political comedy

In his July 14 monologue, Colbert blasted his parent company, Paramount Global, for paying what he called a “big fat bribe” to Trump: a $16 million settlement in a lawsuit over a “60 Minutes” interview with then-Vice President Kamala Harris.

The settlement paralleled one in December between Trump and ABC News, and it came while Paramount sought federal approval to merge with Skydance Media.

“I don’t know if anything will ever repair my trust in this company, but just taking a stab at it, I’d say $16 million would help,” Colbert said in his monologue.

Two nights later, Colbert learned the company was canning his show. His final episode will air in May, and CBS will retire the “Late Show” brand.

CBS said in a July 17 statement that the cancellation was purely a “financial decision,” not influenced by “performance, content or other matters happening at Paramount.”

While Colbert outrates Jimmy Kimmel and Jimmy Fallon at 11:35 p.m., his show lost about half its advertising revenue from 2018 to 2024, and an anonymous CBS source told the New York Post that the show lost between $40 million and $50 million.

Some politicians and entertainers still raised eyebrows.

After Sen. Adam Schiff (D-Calif.) ended an interview with Colbert by turning to the camera and telling Trump to “piss off,” the lawmaker posted on X: “If Paramount and CBS ended the Late Show for political reasons, the public deserves to know. And deserves better.”

Comedian Jena Friedman (Weinberg ’05) sat on a panel for Colbert’s 2016 Election Day special, processing Trump’s unexpected first win on live television.

“As long as Stephen Colbert is on late night, as long as people like him are able to critique the administration freely and brazenly, we’ll be OK,” she recalled thinking at the time. “Our democracy might survive.”

Friedman said she has long felt comfortable exploring controversial topics, including while appearing on programs like Colbert’s. In a 2023 “Late Show” interview, she made a joke about Jeffrey Epstein that she said would “give Stephen something to cut” in editing. To her shock, the final episode kept the joke.

But Friedman self-censors more of her material now. She said Colbert’s cancellation would create a “chilling effect” on freedom of expression, and she called it a “bummer” that networks would take “fewer risks” on comedians like him.

“I’ve always believed that comedians are canaries in the coal mine of democracy,” she said. “When your comedians feel like they can joke about anything, that’s a sign of a healthy democracy.”

Colbert boasted in his July 21 monologue — the first after the fateful announcement — that “the gloves are off.” That monologue racked up about 11 million YouTube views as of Monday evening, and it became Colbert’s most-watched on the site since Jan. 6, 2021, when he lambasted Trump’s response to the attack on the U.S. Capitol.

In 1992, Johnny Carson’s final “Tonight Show” episode attracted an estimated 50 million viewers — a number no one has since replicated live. However, audiences no longer have to tune in to late-night programs before they fall asleep. Comedians can now reach a broader audience when clips from their shows get posted online, said Michael Schneider (Medill ’95), executive editor of TV at Variety.

“There’s no limit to how many people can tune in, and that’s why Colbert, Seth Meyers (Communication ’96), Kimmel, Fallon — they all still have a tremendous impact on popular culture and on the dialogue, and that’s why they’re still so hated by the politicians who they’re skewering,” Schneider said.

The Federal Communications Commission approved the Paramount-Skydance merger on July 24, just weeks after the former company’s settlement and Colbert’s cancellation.

Schneider, Friedman and Colbert’s NU peers all said the “Late Show” host can carve out new opportunities after leaving CBS. However, Schneider said the Trump administration has displayed a willingness to “weaponize” the FCC and other federal agencies against select comedians and journalists.

He also expressed concern about corporations choosing to “bend the knee” to the administration, prioritizing “business” over “free speech.”

“Daily Show” host Jon Stewart, who worked with Colbert on the Comedy Central program for several years, echoed that worry on his July 21 episode.

Stewart brought out a gospel choir at the end of his monologue to sing, “Go f–k yourself.” The same night Colbert directed that message at Trump, Stewart addressed Paramount — the parent company of both CBS and Comedy Central.

Saying ‘yes, and’ to comedy career

When Libera first met Colbert, she thought he hadn’t quite stepped out of his comfort zone. Colbert transferred to NU after two years at Hampden-Sydney College, and Libera recalled telling him that he behaved “as though his clothes were a little too tailored.”

Colbert initially aspired to attend New York University’s Tisch School of the Arts and become a dramatic actor. But life sent him down a different path.

Theatre students took classes under professors like Ann Woodworth (Communication ’75, ’79), studying everyone from Greek playwrights to William Shakespeare to Anton Chekhov.

Colbert’s former roommate Christopher Baker (Communication ’85) now applies those lessons as a director, playwright and professor at the University of Massachusetts Amherst. He said Colbert applied the lessons about dramatic acting in a more comedic context.

“‘The Colbert Report,’ if it was to be successful — he had to understand, ‘How can I maintain this not only for a whole episode, but for a whole season and more? What is the long arc of all of this?’” Baker said.

In addition to acting in plays, Colbert showcased his improvisational skills on campus with the group No Fun Mud Piranhas. He performed alongside peers like “Friends” star David Schwimmer (Communication ’88) and Alan Goldwasser (Communication ’87), who now runs a consignment business, bigalgie Vintage.

Goldwasser noted one performance at an Evanston bar where the group performed a Harold routine, acting out a series of scenes that build on and eventually connect with each other. Colbert brought that night’s routine together by imitating the popping of a wine cork, and Goldwasser recalled the “spontaneous laughter and applause” that followed.

“That’s Stephen: just very quick, very smart, and that’s exactly what you want,” Goldwasser said.

Baker said Colbert possessed the “perfect personality” for improv because he embodied the idea of “yes, and,” through which an improviser accepts and builds on other improvisers’ ideas instead of rejecting them.

The emerging comedian applied this mindset even outside of improv performances: Baker said the “optimistic” Colbert would brainstorm ideas for collaboration and build on peers’ comments by saying, “Oh, that’s a great idea, and…”

Libera helped Colbert land a post-college job working the box office at The Second City in Chicago, where she now serves as director of comedy studies in addition to teaching at Columbia College Chicago and NU. She said Colbert mastered two different sides of effective improv: talking out his own ideas and listening to others’ ideas.

As an effective listener, he can “reflect” others’ comments back at them — a skill he often practices in “Late Show” interviews, Libera said.

Colbert joined The Second City’s touring improv company in 1988, where he met performers like Steve Carell, Paul Dinello and Amy Sedaris. After Dinello and Sedaris cast Colbert in the sketch comedy series “Exit 57,” the comedian told Posner on a bus ride to The Second City that he planned to move somewhere bigger: New York City. At the time, Posner thought Colbert was an “idiot” and feared the Big Apple would eat him alive.

“Exit 57” only lasted 12 episodes. “The Dana Carvey Show,” another program featuring Colbert, lasted seven. But those short-lived stints preceded Colbert’s runs on “The Daily Show” and beyond, and Posner said he was “thrilled” Colbert proved him “utterly wrong.”

“He had the goods to back it up, but a lot of people don’t even have that kind of confidence or that kind of clarity of sight that he did,” Posner said.

Responding to hardships and hatred

Woodworth remembered Colbert putting on a “constant comic performance” during class, in the hallways and on various stage productions. But she said he, like other students, struggled in class to grasp the tragedy of shows like “Hamlet” and “Medea.”

Colbert himself faced a tragedy growing up: A plane crash in 1974 killed his father and two of his brothers when he was just 10. Afterward, Colbert sought to cheer his mother up by making her laugh.

Woodworth described him as someone who faced an “unimaginable crisis” in childhood and later carved out a life “with grace and with sensitivity and humility.”

Colbert recorded a video for the 2020 graduation at NU’s Qatar campus, coinciding with the end of Woodworth’s time teaching there. Several of his peers have similarly remembered him as compassionate and generous, both during and after college.

Colbert’s ability to focus on specific people sometimes diverted him socially, but Halliday, his ex-girlfriend from college, said it also made him a better friend.

“More than most straight white guys in 1987 that were his age, he had some emotional intelligence and ability to support others,” Halliday said. “That could be a thing where he kind of lost track of time or whatever, and he would stay with these friends for a really long time.”

Colbert visited Woodworth when he served as NU’s Homecoming grand marshal in 2006, and he named her during a 2018 NU event as someone who changed his life. Now, Colbert prepares for another change in his life — and though Woodworth recognized the pain he may have felt losing a job he loved, she said “The Late Show’s” cancellation could be “one of the best things to happen to him.”

She said Colbert can use his talents outside of a late-night formula she views as “tired.”

“I just feel like there’s something more or something bigger or something greater, something more impactful, waiting for him,” Woodworth said.

Colbert could follow the lead of David Letterman, his “Late Show” predecessor, or of Conan O’Brien, another talk show host forced out in controversial circumstances. Both hosts followed up their network TV runs by growing beards and starting new shows.

Or Colbert could follow his own alter ego’s lead and run for president. That character launched and quickly ended a presidential campaign in the 2008 cycle.

But Posner — currently a director, playwright and American University professor — predicted the real Colbert is thinking about ways to support other people, not himself. He recalled a 2009 interview with Colbert that raised funds for Two River Theater, a nonprofit organization where Posner previously served as artistic director.

Posner said he has spoken with Colbert about “what Trump’s hatred for him might accomplish in the world.” He views his peer and friend as a “hero,” saying Colbert has used his platform to promote hope, connection and kindness.

With CBS axing “The Late Show,” Posner joins Colbert’s other friends and fans in awaiting his next move.

“It just feels obvious that this was an act of aggression, and I will be eager to see how Stephen meets it: probably with an act of compassion, not for Trump but for the world,” Posner said.

Email: [email protected]

X: @edwardsimoncruz

Bluesky: @edwardsimoncruz.bsky.social

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