Sat. Aug 9th, 2025
alert-–-late-night-gone-woke:-cringiest-moments-of-hosts-who-prioritized-liberalism-over-laughs-as-stephen-colbert-sackedAlert – Late night gone WOKE: Cringiest moments of hosts who prioritized liberalism over laughs as Stephen Colbert sacked

The curtain has fallen on Stephen Colbert’s Late Show, sparking more buzz than one of his fiery Trump monologues.  

Depending on who you ask, Colbert was either a fearless truth-teller crushed by corporate politics — or a comic who let the jokes slide in favor of political lectures, and the ratings suffered as a result.

CBS pointed to declining ad revenue after 10 seasons, while critics claimed the host prioritized preaching over punchlines.

Fans, however, praised him as a clever satirist caught in the crossfire of CBS and Paramount’s $8-billion merger — a convenient pawn in the network’s effort to appease President Donald Trump.

Back in the day, Johnny Carson kept late night an equal-opportunity laugh zone so as not to alienate potential viewers – a tradition Jay Leno carried on and who just recently weighed in on Colbert’s exit by asking, ‘Why shoot for half an audience? Why not try to get the whole?’ 

With that in mind, Daily Mail is revisiting late night’s cringiest ‘woke’ moments — when the jokes took a backseat to ideology.

The recent cancellation of Stephen Colbert 's The Late Show has prompted a firestorm of debates at the cross-section of entertainment and politics - as to whether the late night landscape punted on profits over political correctness

The recent cancellation of Stephen Colbert ‘s The Late Show has prompted a firestorm of debates at the cross-section of entertainment and politics – as to whether the late night landscape punted on profits over political correctness

The sentiments against President Donald Trump over the past decade have consumed many of the comics working the evening hours. Trump pictured at the NATO Summit on June 25

The sentiments against President Donald Trump over the past decade have consumed many of the comics working the evening hours. Trump pictured at the NATO Summit on June 25 

 

Stephen Colbert pushes the vaccine

Colbert was no stranger to left-leaning politics dating back to his time on The Daily Show before taking over David Letterman’s coveted 11:30 spot for CBS in 2015.

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In his 10 seasons – which spanned from Trump’s declaration he was running in 2016 through now – he devoted significant chunks of his show to political chatter, with some now saying it might not have made for the best business move.

The partisan politics dripped into the booking of guests as well, as he had on left-wing media personalities such as Anderson Cooper – 21 times – as well as Joy Reid, Rachel Maddow, Jake Tapper and George Stephanopoulos.

Amid the divisiveness of the coronavirus vaccine mandates under then-President Joe Biden, Colbert steered his show toward activism in taking a direct approach in telling his viewers to get vaccinated.

When Biden forced federal employees to be vaccinated or risk losing their jobs, Colbert said, ‘Good! Good, I say! Finally, the federal government has reached the high standard of audience for a comedy show.’

The most egregious instance appeared to be a June 2021 sketch titled The Vax-Scene, in which the late night host took a Schoolhouse Rock approach to persuading his viewers to get the jab.

Colbert starred in a June 2021 sketch titled The Vax-Scene, in which the late night host took a Schoolhouse Rock approach to persuading his viewers to get vaccinated

Colbert starred in a June 2021 sketch titled The Vax-Scene, in which the late night host took a Schoolhouse Rock approach to persuading his viewers to get vaccinated 

When then-President Joe Biden forced federal employees to be vaccinated or risk losing their jobs, Colbert expressed his approval on the air

When then-President Joe Biden forced federal employees to be vaccinated or risk losing their jobs, Colbert expressed his approval on the air 

 

Jimmy Kimmel cries over Trump’s 2024 win 

Kimmel rose to stardom decades back on Comedy Central’s The Man Show – a program choc full of blackface skits and misogynistic humor.

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But he’s seemingly reinvented himself as a teary-eyed social crusader over the past decade with Trump taking over the U.S. political discussion, frequently getting emotional and preachy during his monologues.

It marked a far cry from the brilliant, brash entertainer who proved his razor-sharp wit on many occasions prior to on his ABC late night show.

The softening shift also appeared to mimic a career path previously taken by  one of Kimmel’s closest friends and show business heroes, radio icon Howard Stern. 

Kimmel’s political views were on naked display on the November 6, 2024 edition of Jimmy Kimmel Live, in the wake of Trump’s dominating victory over Democratic challenger Kamala Harris.

He said:  ‘It was a terrible night for women, for children, for the hundreds of thousands of hard working immigrants who make this country go, for health care, for our climate, for science, for journalism, for justice, for free speech.

‘It was a terrible night for poor people, for the middle class, for seniors who rely on Social Security, for our allies in Ukraine, for NATO and democracy and decency.

Kimmel continued: ‘And it was a terrible night for everyone who voted against him. And guess what? It was a bad night for everyone who voted for him too. You just don’t realize it yet.’

The emotional host wrapped up in declaring that ‘it was a really good night for Putin and for polio and for lovable billionaires like Elon Musk, and the bros up in Silicon Valley, and all the wriggling brain worms who sold what was left of their souls to bow down to Donald Trump.’

Kimmel's political views were on naked display on the November 6, 2024 edition of Jimmy Kimmel Live, in the wake of Trump's dominating victory over Democrat Kamala Harris

Kimmel’s political views were on naked display on the November 6, 2024 edition of Jimmy Kimmel Live, in the wake of Trump’s dominating victory over Democrat Kamala Harris 

Fallon later said of the gag: 'I didn't do it to humanize him. I almost did it to minimize him'

Fallon later said of the gag: ‘I didn’t do it to humanize him. I almost did it to minimize him’

 

Jimmy Fallon grovels over Trump bit

Jimmy Fallon, one of Carson’s successors, has not generally been geared towards political messaging, but even he got caught in the fray in 2016 during Trump’s first presidential campaign against Democrat Hillary Clinton.

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When Trump appeared on The Tonight Show in September of 2016, Fallon kept the banter light with the Republican presidential candidate and even moussed his hair at one point.

Polls said that appearance was a huge win for Trump, who upset his heavily-favored opponent two months later. 

Fallon had to humiliatingly walk back his actions in an interview with The New York Times five months after Trump took office in May 2017. 

‘If I let anyone down, it hurt my feelings that they didn’t like it. I got it,’ Fallon told the paper. ‘I didn’t do it to humanize him. I almost did it to minimize him.

‘I didn’t think that would be a compliment: ‘He did the thing that we all wanted to do.”

Fallon called himself a ‘people-pleaser’ and said he was upset at the reaction to his softball interview with Trump.

‘If there’s one bad thing on Twitter about me, it will make me upset,’ he said. ‘So, after this happened, I was devastated. I didn’t mean anything by it. I was just trying to have fun.’

Seth Meyers secured his place in the ‘woke late-night’ hall of fame in March 2023, targeting Republicans

Seth Meyers secured his place in the ‘woke late-night’ hall of fame in March 2023, targeting Republicans

 

Seth Meyers’ brutal swipe at Republicans

Seth Meyers earned his spot in the ‘woke late-night’ hall of fame in March 2023, when he took aim at Republicans for what he saw as their endless search for ‘some new culture war issue’ — this time, washing machines.

The former SNL writer rolled clips of Fox News commentators fuming over eco-friendly appliance regulations, before quipping that the only real kitchen crisis was that ‘dishwashers are too quiet now.’

He accused Republicans of having ‘no discernible policy agenda aside from whining about wokeness — a term they can’t even define.’

At the time, Florida Governor Ron DeSantis had been railing against an ‘oppressive woke-ocracy,’ a phrase Meyers joked ‘probably gives you strep throat’ just saying it — and was clearly too much of a mouthful for Donald Trump to pronounce.

From there, he mocked GOP attempts to connect the collapse of Silicon Valley Bank to ‘diversity,’ scoffing, ‘I’m tired of all these radical leftist banks. If a bank can be woke, then literally anything can be woke.’

Fast forward to November 2024, and Meyers had a mini on-air meltdown after Trump’s election win. 

‘I don’t think Donald Trump is a good person — in fact, I’ll go as far as to say he’s a bad person,’ he said. ‘Now, in my defense, I’m only basing that on everything I’ve ever learned about what makes someone good or bad.’

He wrapped the segment with biting sarcasm: ‘All hail our powerful and benevolent leader.’

 

Where it all began: The 2011 White House Correspondents’ Dinner 

While Trump’s flirtation with the presidency dates back at least four decades, many attribute his attendance at the 2011 White House Correspondents’ Dinner – and humiliating jokes lobbed in his direction – as the real as trigger to him officially entering the political arena about four years later.

It was there that then-President Barack Obama torched his unlikely successor with the series of sharp jabs after Trump had been a thorn in his side with his birther claims.

‘Donald Trump is here tonight,’ Obama said as Trump silently absorbed the abuse while in the audience. ‘Now I know that he’s taken some flak lately. But no one is happier – no one is prouder – to put this birth certificate matter to rest than The Donald.’

Obama continued, ‘And that’s because he can finally get back to focusing on the issues that matter: Like, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?’

In May of 2011, then-President Barack Obama mocked the idea of Trump being presidential timber, pointing to his work with faded stars on The Celebrity Apprentice

In May of 2011, then-President Barack Obama mocked the idea of Trump being presidential timber, pointing to his work with faded stars on The Celebrity Apprentice 

Trump silently absorbed the abuse while in the audience, with a number of analysts saying the evening inspired his unlikely campaign four years later

Trump silently absorbed the abuse while in the audience, with a number of analysts saying the evening inspired his unlikely campaign four years later 

Obama mocked the idea of Trump being presidential timber, pointing to his work with faded stars on The Celebrity Apprentice.

‘All kidding aside, obviously we all know about your credentials and breadth of experience,’ Obama said. ‘For example … no seriously, just recently, in an episode of Celebrity Apprentice, at the steakhouse, the men’s cooking team did not impress the judges from Omaha Steaks.

‘And there was a lot of blame to go around, but you, Mr. Trump, recognized that the real problem was a lack of leadership, and so ultimately you didn’t blame Lil Jon or Meat Loaf, you fired Gary Busey!’

He added, ‘And these are the kinds of decisions that would keep me up at night. Well handled, sir. Well handled.

Late Night host Seth Meyers also might have provided some grist for Trump’s political mill with a sharp crack that left Trump reeling in the crowd.

‘Donald Trump has been saying that he will run for president as a Republican – which is surprising, since I just assumed that he was running as a joke,’ Meyers said. 

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