One of the biggest moments in Stephen Colbert’s life and career will forever be a choice somebody else made for him.

Following his July 17 revelation that CBS was canceling “The Late Show with Stephen Colbert” after one more season, headlines blazed about Colbert. Was the show canceled because late night TV is a relic of the past? Was the cancelation politically motivated? What does this mean for the future of the industry? What does it mean for Stephen Colbert?

The highly successful and popular comedian, 61, has been an institution in late night TV for nearly three decades, starting in the weird world of sketch comedy and eventually making his way to a desk first occupied by the legendary David Letterman. Over his career he has mocked President George W. Bush to his face at an infamous White House Correspondents Dinner, held a Washington, D.C. rally with friend and colleague Jon Stewart, published books, hosted award shows and the Kennedy Center Honors, won 10 Emmy awards, two Grammy Awards and five Peabody Awards. He has even gotten his own Ben & Jerry’s ice cream flavor.

Colbert may only have 10 months left at CBS hosting “Late Show” in the iconic Ed Sullivan Theater, but that doesn’t mean the prolific entertainer is likely done. Here’s a look back at his career, personal life and biggest moments.

How did Stephen Colbert get started in comedy?

Colbert got his start in Chicago’s Second City Comedy Troupe, which also was the launchpad for such famous faces as Tina Fey, Amy Poehler, John Candy, Steve Carrell, Mike Myers and many more. Colbert was a member of the group in the late 1980s and early 1990s, and met comedians Amy Sedaris and Paul Dinello, with whom he would later work on Comedy Central series “Exit 57” (1995-1996) and “Strangers with Candy” (1999-2000). He auditioned for “Saturday Night Live” twice but never made the cut (you can find footage of his auditions in the recent Peacock documentary “SNL50: Beyond Saturday Night”).

‘Stephen Colbert’ joins ‘The Daily Show’ and ‘The Colbert’ Report

His big break came when he joined the cast of “The Daily Show” in 1997, while it was still hosted by Craig Kilborn. When Jon Stewart took over as host in 1999, it became more overtly political. Colbert soon developed a character for himself, a parody of conservative political pundits loosely based on Bill O’Reilly, then on Fox News. He was a staple on “Daily” until 2005, when the popularity of his character led to the creation of spinoff “The Colbert Report.”

Colbert hosted “Report” from 2005-2014 as “Stephen Colbert,” in his trademark frameless spectacles and with a fierce commitment to never breaking character, no matter what news he was covering. It more directly satirized elements of cable-personality news opinion shows like “The O’Reilly Factor,” “Hannity” and “Glenn Beck” that dominated Fox News in that era.
While he hosted “Report,” Colbert’s fame and popularity surged and led to some of his biggest career moments. In 2006 he was asked to host the White House Correspondents Dinner, and used that platform to lambast the president and the media that were gathered in front of him. “I stand by this man because he stands for things,” said Colbert, in his character as his pundit persona. “Not only for things, he stands on things. Things like aircraft carriers and rubble and recently flooded city squares. And that sends a strong message, that no matter what happens to America, she will always rebound – with the most powerfully staged photo ops in the world.”
In 2010 he and Comedy Central colleague Stewart each held rallies in Washington, D.C., aimed at satirizing Glenn Beck’s “Restoring Honor” rally. Stewart hosted the “Rally to Restore Sanity” while Colbert’s event was the “March to Keep Fear Alive.” The events were eventually merged into the “Rally to Restore Sanity and/or Fear,” attracting an estimated 215,000 people, according to CBS News.

Colbert took over for David Letterman in 2015

But “Stephen Colbert” was left behind and the real Stephen Colbert emerged in 2014, as CBS announced that David Letterman would be retiring from his desk at “The Late Show,” which he had manned on the network since 1993. The former Comedy Central star made the move to network TV in 2015, when the first episode of “The Late Show with Stephen Colbert” aired on Sept. 8.

Colbert’s version of the show was, unsurprising to anyone who had followed his career, far more overtly political than Letterman’s iteration. While the original “Late Show” host had a fascination with celebrity and Hollywood, Colbert kept his monologues largely focused on Washington and world events, though his guests were mostly the usual parade of actors, musicians and directors hawking their latest projects. He was able to wrangle far more politicians, lawmakers and newscasters to his couch, including Sen. Adam Schiff, D-Calif., who was a guest on the July 17 episode in which Colbert announced the fateful cancelation news.

Colbert’s political slant was often a boon to ratings and publicity for CBS, which frequently gave the host special live shows and specials on the network and sister premium network Showtime coinciding with big political events, including the Democratic and Republican National Conventions and election nights. During the early days of the COVID-19 pandemic, Colbert remained an active host, initially for surreal audience-less episodes at the Ed Sullivan Theater, and then from his home.

Colbert’s personal life has included grief, love and faith

Colbert, who was born the youngest of 11 children from a devout Roman Catholic household, has been open about his faith throughout his time behind the desk. He met and married his wife of 31 years, Evelyn “Evie” McGee Colbert in 1993, and the pair share three children: Madeleine, Peter and John. Evelyn has been a feature on “Late Night,” particularly during the COVID-19 pandemic and around major holidays.

The comedian lost two of his older brothers and his father in plane crash when he was just 10. The 1974 accident killed over 70 passengers. “There’s this big break in the cable of my memory at their death. Everything before that has got an odd, ghostly tone,” Colbert told Anderson Cooper in 2019.

What does ‘The Late Show’ cancelation mean for Colbert’s future?

Colbert himself had very little to say about the decision by CBS and its parent company, Paramount. “It’s not just the end of our show, but it’s the end of ‘The Late Show’ on CBS. I’m not being replaced. This is all just going away,” he said after audible boos from his in-studio audience, going on to thank the audience and many people involved in making the show. “Let me tell you, it is a fantastic job. I wish somebody else was getting it, and it’s a job that I’m looking forward to doing with this usual gang of idiots for another 10 months. It’s going to be fun!”