All the Times Stephen Colbert Went Too Far

Stephen Colbert rose to fame in the late 1990s as a correspondent on The Daily Show. Then, in 2005, he went into perpetual-parody mode as the Fox News-style anchor of Comedy Central’s The Colbert Report.

His notoriety and ability to be inherently likeable, even at his most obnoxious, led to one of the most coveted gigs a comedian can hope for. Since September 2015, he’s been the host of CBS’ The Late Show, and by most accounts it’s been a match made in heaven. As of May 2017, he’s helped boost ratings for the talk show.

Colbert is not the first late-night talk show host to say something controversial. And it’s safe to say he won’t be the last. But he has had his share of “wow, he went there” moments when he pushed guests, and even viewers, outside of their comfort zone.

Here are 13 moments where Stephen Colbert might have gone just a bit too far, ranked from least to most offensive.

13. Insensitivity to the Asian community

A tweet from the Colbert Report twitter account says, 'I am willing to show #Asian community I care by introducing the Ching-Chong Ding-Dong Foundation for Sensitivity to Orientals or Whatever.'

An insensitive tweet from The Colbert Report Twitter account. | The Colbert Report via Twitter

During his time on The Colbert Report, Colbert did an exceptional job of mocking, and thus providing humorous commentary on, over-the-top cable TV punditry. But in 2014, he took his parodying of the right wing news media a bit too far and wound up actually offending an entire community.

When Washington Redskins owner Dan Snyder responded to backlash over his team’s name by creating the Washington Redskins Original Americans Foundation, the Colbert Report’s social media team responded. A tweet from their account said, “I am willing to show #Asian community I care by introducing the Ching-Chong Ding-Dong Foundation for Sensitivity to Orientals or Whatever.”

It didn’t go over well. And though Colbert himself allegedly had nothing to do with the tweet, which many felt was racist, much of the backlash that ensued was directed at him. But despite a #CancelColbert campaign, Comedy Central did not, in fact, take him off the air.

12. Interviewing Julian Assange

Julian Assange smiles during an interview on 'The Colbert Report.'

Julian Assange on The Colbert Report | Comedy Central

Colbert spent years interviewing political figures on both sides of the aisle. That’s likely a large part of what helped him land his gig on Late Night. But in some cases, he booked guests on The Colbert Report that were a bit too controversial.

In 2011, he sat down for a conversation with WikiLeaks founder Julian Assange. Their conversation was, in and of itself, a lightning rod for debate. Assange has long been critical of the United States federal government and its diplomatic methods, and he didn’t hold back during his conversation with Colbert.

However, Assange is not without his own skeletons. He’s been accused of rape and sexual assault. So it’s worth examining whether Colbert should have given him a platform to espouse his views on others’ potentially illegal actions when he’s currently hiding out to escape prosecution for his own.

11. Making Barney Frank uncomfortable

Barney Frank being interviewed at the Brookings Institute.

Barney Frank | Chip Somodevilla/Getty Images

One of The Colbert Report’s most popular segments was also one of its most obscure. In “Better Know a District,” he profiled and interviewed the various congressional regions of the United States — often to hilarious results. But when he sat down in October 2005 with Barney Frank, then the representative for Massachusetts’ 4th Congressional District, it got distinctly uncomfortable.

Colbert mocked Frank’s weight and “lefty” tendencies — the former congressman is both unabashedly liberal and left-handed. And he feigned ignorance about the fact that Frank is gay, asking him pointed questions about his wife. Frank seemed unprepared to deal with Colbert’s over-the-top antics and was visibly uncomfortable during the interview.

10. Going soft on Henry Kissinger

Henry Kissinger, wearing a suit, standing in front of a black door.

Henry Kissinger | Leon Neal/Getty Images

In 2016, Jimmy Fallon faced a great deal of backlash for the fluffy interview he conducted with then-presidential candidate Donald Trump. Throughout his time on The Colbert Report, Colbert gave former Secretary of State Henry Kissinger a similarly light treatment — and in retrospect, that was not a great decision.

In a segment featuring numerous other public figures, Colbert danced through Washington, D.C., with Kissinger. In another 2006 segment, he featured Kissinger as a judge in a mock trial.

Kissinger is, to put it lightly, a figure that has deeply divided American opinion. Some feel he was a strong and effective diplomat; others have accused him of being a war criminal. So, given his controversial status, Colbert’s decision to treat Kissinger as cute and cuddly during their interview segment was in poor taste.

9. Interviewing Barbara Lee

Stephen Colbert sits next to a screen that's displaying a photo of Rep. Barbara Lee on 'The Colbert Report.'

The Colbert Report | Comedy Central

When your alter ego is a total egomaniac with absolutely zero sense of political correctness, you’re going to ruffle a few feathers now and then. But Colbert once again got a little too Colbert-y when he interviewed Rep. Barbara Lee for his “Better Know a District” series.

While the representative did an admirable job of going with the flow, Colbert asked Lee awkward question after awkward question relating to her race. He asked her about her “urban” background and the Black Panthers. Lee, who represents California’s 13th Congressional District, was mostly unimpressed and obviously uncomfortable during parts of their exchange. The tension between the two was so apparent that the entire segment felt decidedly unfunny.

8. His Bill O’Reilly send-off

In some ways, Colbert owes his career to Bill O’Reilly. After all, his Colbert Report character was obviously inspired by the former The O’Reilly Factor host. So it was a no-brainer when he devoted a piece of his Late Night monologue to sending off O’Reilly after he was fired from Fox News following allegations of sexual assault.

Colbert didn’t exactly put the “good” in “goodbye” during his send-off though. He held no punches in assessing O’Reilly’s impact, calling him “a self-righteous landfill of angry garbage.” O’Reilly’s detractors would argue his vitriol made him a prime target for this level of criticism. But his supporters were at the very least miffed that Colbert was kicking their guy while he was down.

7. Rallying for extreme viewpoints

Stephen Colbert and Jon Stewart stand side-by-side, holding microphones and waving to the crowd, at their rally on the National Mall.

Stephen Colbert and Jon Stewart | Win McNamee/Getty Images

One of the things fans liked best about The Colbert Report was the frequent back and forth between Colbert and his Daily Show counterpart, Jon Stewart. So when the two hosts announced events in Washington, D.C., viewers were especially excited.

The 2010 event, Rally to Restore Sanity and/or Fear, was designed to point out the extremes in varying viewpoints in United States politics. And while it drew more than 200,000 people to the National Mall, not everyone was impressed by the outcome. Bill Maher felt the joint rally created a false sense that the left and right were equally to blame for the discord in American politics.

6. Interviewing Robert F. Kennedy Jr.

Robert F. Kennedy Jr. sitting at a table during an interview on 'The Colbert Report.'

Robert F. Kennedy Jr. | Comedy Central

During his time on The Colbert Report, Colbert often asked some pretty direct questions to his interview subjects. And while that was sometimes perceived as refreshing, given the softball questions some mainstream journalists were prone to asking, it sometimes made for exceedingly weird situations.

That was definitely the case when he interviewed Robert F. Kennedy Jr. in 2006. The activist and author faced off with Colbert to defend his Rolling Stone article that claimed George W. Bush had stolen his 2004 election. Colbert turned the tables on Kennedy Jr. and asked him whether his uncle, John F. Kennedy, had stolen his own electoral victory. The uncouth question clearly caught Kennedy Jr. off guard and was seen by some as crossing a comedic line.

5. Debating with Mandy Patinkin

Mandy Patinkin, looking unamused, during an interview on 'The Colbert Report.'

Mandy Patinkin | Comedy Central

By the time The Colbert Report closed up shop in 2014, most of the series’ guests knew what to expect when they sat down for an interview. They would be asked blunt questions, it would be uncomfortable, and it was all in the name of comedy.

Unfortunately, in 2012, actor Mandy Patinkin didn’t get that memo. And as a result, things got heated between him and Colbert when he sat down for an interview. Patinkin was visibly tense while Colbert grilled him about his progressive politics, and he even accused Colbert of peddling propaganda. Colbert, to his credit, never broke character, but maybe he should have for the sake of Patinkin’s blood pressure.

4. Filing for a super PAC

Stephen Colbert holds his ear like he's trying to hear what someone is saying to him.

Stephen Colbert | Alex Wong/Getty Images

In 2011, Colbert announced he would be forming a super PAC, Americans for a Better Tomorrow, Tomorrow. Though the name of his political action committee was humorous, its intent was anything but. In reality, Colbert hoped to use the super PAC to teach viewers, and Americans at large, about the extraneous power these types of committees can have in our political system. And it seemed to work.

But Colbert’s super PAC also tested the limits of American election law, according to some experts. The committee in charge of approving the PAC, the SEC, struggled to figure out where The Colbert Report and its host began and Viacom, the corporation that owned the series, ended. Colbert’s seemingly simple request was, in fact, a big deal for those who had to figure out how to make it work.

3. Hosting the White House Correspondents’ Dinner

The White House Correspondents’ Dinner is a time-honored Washington, D.C., tradition. It allows for a night of fun, frivolity, and a whole lot of lighthearted roasting of the president and other major political figures.

In 2006, Colbert hosted the event in character as his Colbert Report alter ego. And in his 20-minute speech, he didn’t hold back when it came to going after then-president George W. Bush, his policies, and the media in general, all while the targets of his jokes sat a few feet away from him.

The speech became the subject of numerous debates among pundits and online. Some felt he took his remarks too far, while others praised his bold, no-holds-barred approach.

2. Testifying to Congress while in character

In 2010, Colbert appeared before the Senate Judiciary Committee. In retrospect, they probably shouldn’t have been surprised his Colbert Report alter ego showed up in his place.

Colbert testified, in character, on behalf of an initiative for migrant farm workers, and many of the people in the room were not amused. In response to his sarcastic and uber-conservative remarks, which mentioned everything from bikini waxes to colonoscopies, some felt he had taken his act to the extreme in a setting that’s allegedly reserved for the utmost decorum.

1. Going after the president

Colbert hasn’t been shy about his disdain for President Donald J. Trump. And the president has been the frequent butt of his jokes since he took office. But during Colbert’s May 2, 2017, monologue, his ire toward the man in the Oval Office took a turn into NSFW territory.

Colbert was miffed that Trump was dismissive of his friend and colleague, John Dickerson, during an interview. So he unleashed a litany of insults in his defense. In addition to calling the commander in chief a “pr*cktator,” he said, “The only thing your mouth is good for is being Vladimir Putin’s c*ck holster.”

The comment drew gasps from the audience — and an immediate and widespread backlash. Some felt it wasn’t just inappropriate, but homophobic, and a #FireColbert campaign began on social media. Thus far, his place at The Late Show seems to be pretty secure.

Read More: 25 Most Controversial TV Show Moments of All Time

Follow Katherine Webb on Twitter @prufrox.

Check out Entertainment Cheat Sheet on Facebook!