Colbert's brutal takedowns revealed ahead of Prince Harry interview

The savage on-screen takedowns that will have the palace bracing for disaster: FEMAIL reveals acerbic late-night host Stephen Colbert’s most BRUTAL moments ahead of interview with Prince Harry – from mocking Trump to slamming ‘racist’ Monarchy

  • Stephen Colbert, 58, as the king of late night, is spoiled for interview choices
  • But tonight he’ll be sitting down with one of the most famous: Prince Harry
  • Known for his cutting wit, Colbert is the only US late night host to interview royal
  • FEMAIL looks back at Colbert’s scathing – and sometimes awkward – moments 

As the king of late night, Stephen Colbert has been spoiled for interviews, but he has just sat down with one of his most famous subjects yet: Prince Harry.

Known for his cutting wit, the 58-year-old host of The Late Show With Stephen Colbert gave us a taster of what to expect, showing us that no one, not even royalty, can dodge his silver-tongued gibes, including the Duke of Sussex, who has penned an explosive memoir, Spare, that has sent shockwaves across the palace.

Previewing the interview, which will air tonight, Colbert teased Harry’s appearance on Monday night, with the comedian comparing the royal’s life to Harry Potter and joking the new book is available as a royal commemorative plate.

After playing a clip where Harry describes his pain at William trying to avoid him at Eton, the Late Show presenter quipped: ‘That’s heartbreaking. To be rejected by his older brother at school even though that magic hat sorted them into the same house. What do you think? Hufflepuff? Gryffindor?’

Prince Harry, Duke of Sussex, is seen leaving The Late Show With Stephen Colbert on Monday night

Harry also downed tequila shots during the interview, which will air tonight

In a trailer for tonight’s show, Stephen Colbert appeared more focused on poking fun at Harry and his bitter rift with his brother, William, and scathing gags about Britain and the royals including the late Queen. Harry also downed tequila shots during the interview.

Fans attending the recording at the Ed Sullivan Theater told DailyMail.com the Duke of Sussex answered a series of questions from the late night host in his Colbert Questionert segment.

Just hours before the much-anticipated interview airs, FEMAIL looks back at the scathing – and sometimes awkward – moments from Colbert, including his brutal political takedowns to his hilarious reaction to Meghan Markle’s Oprah interview.

The Late Show host lampooned Donald Trump, even before he was president

Before he was President, Trump appeared on The Late Show in 2015 where Colbert first struck a reconciliatory with the would-be Commander-in-Chief.

‘I also want to apologize to you because I said a few things about you over the years that are in polite company perhaps are unforgivable,’ the host says.

To which Trump responds: ‘Almost… and some nice things.’

But Colbert disagrees, saying: ‘I don’t remember saying anything nice.’

Trump appears on The Late Show in 2015. During the interview, Colbert could not maintain his composure

Offering Trump an olive branch, Colbert also provided the former President with the opportunity to apologize for his wrongs. ‘Uh no,’ Trump responded

https://youtube.com/watch?v=Ns7ocpRhDD8%3Frel%3D0%26showinfo%3D1%26hl%3Den-US

The audience bursts into applause and laughter.

Offering Trump an olive branch, Colbert also provides the former President with the opportunity to apologize for his wrongs.

‘Uh no,’ Trump responds.

The pair then move onto immigration and the border wall issue.

‘We have to have a border, and in that wall, we’re going to have a beautiful big, fat door,’ Trump says.

The audience can’t contain their amusement and neither can Colbert who loses his composure at his guest’s declaration.

Later in the interview, Colbert asks him a question that will be ‘the last time you ever have to address this question if you hit the ball.’

In another biting commentary on the former President, Colbert compared the then Republican presidential candidate to a Nazi in 2016

https://youtube.com/watch?v=Eh_GFkdxwbQ%3Frel%3D0%26showinfo%3D1%26hl%3Den-US

‘There’s like sauce all over my hands, this meatball is so big,’ the host continues.

‘Barack Obama, born in the United States?’

Will Stephen Colbert and Prince Harry bond over shared experience of losing their parents at a young age?  

Stephen Colbert’s father and two brothers died in a 1974 plane crash when he was aged 10.

He opened up about his experience of grief with CNN anchor Anderson Cooper, who also lost his father at the age of 10, in a moving interview in 2019.

Cooper said he had been reflecting on his grief after his mother, Gloria Vanderbilt, had died earlier that year.

‘You wrote me a letter after my mom died,’ he reminded Colbert during the interview. 

‘In it you said, “I hope you find peace in your grief.” One of the things I’ve been thinking a lot about is how we don’t really talk about grief and loss. People are not comfortable talking about it.

‘You’ve spoken very publicly about what you experienced as a kid — a lot of it I didn’t know. I think a lot of people don’t know. So if you don’t mind, I wanted to talk to you a little about it and sort of how it has shaped who you are now.’

Speaking about his grief, Colbert said: ‘You become a different person. I was personally shattered, and then you kind of reform yourself in this quiet, grieving world that was created in the house.

‘It became a very quiet house and very dark, and ordinary concerns of childhood suddenly kind of disappeared… I had certainly a different point of view than the children around me.’

Stephen Colbert and Anderson Cooper spoke about grief in a 2019 interview

Colbert then mimes throwing his metaphorical meatball into the air before the audience cheers again.

Trump, who appears unamused, says: ‘I don’t talk about it anymore.’

In another biting commentary on the former President, this time a reaction to Trump’s response following the 2016 Orlando gay nightclub shooting that killed 49 people.

Colbert compared the then Republican presidential candidate to a Nazi after Trump made a speech criticizing then President Obama’s reaction to the horrific tragedy.

‘We’re led by a man that either is not tough, not smart, or he’s got something else in mind… There is something going on,’ Trump said during the speech.

Colbert said he considered himself one of those ‘people’ before making his way to a chalkboard and drew out a ‘Figure-It-Out-Atron’ to work out what Trump was getting at.

The host wrote the words Muslim, Bad Thing, Not Smart, Radical Islam, Something Going On, Inconceivable, Obama, Trump in a clockwise configuration on the chalkboard.

Then after a short monologue he connected several of the words to create a swastika shape.

Editing responses from the then president’s 2017 Face The Nation TV appearance about his first 100 days in office, Colbert skewered Trump in a parody interview where the host asks: ‘Sir, you’ve been in office for a 100 days, what do you think people are saying about you?’

The President has then been edited to respond: ‘People are asking is he sane? I have no idea.’

Colbert adds: ‘You don’t know if you are sane or not?’

To which, Trump says: ‘I don’t know, I mean we’ll see.’

The video then cuts to Colbert who begins speaking about North Korea, asking: ‘Are you afraid you might start a nuclear war?’

Trump’s response: ‘I was all set to do it. In fact I was going to do it today, I was going to do it as we’re sitting here, I would have had to delay you.’

‘Do you understand the ramifications of a nuclear holocaust?’ Colbert asks.

‘No’ is Trump’s edited answer.

‘All of life on earth would be wiped out,’ Colbert says, ‘You know that would also include your golf courses.’

‘I would not be happy,’ Trump says.

Colbert also skewered Trump in a 2017 parody interview, which edited from his responses


Trump (left) shoots back his edited responses in the parody interview with Colbert (right)

The host then asks Trump what his stance of NAFTA and Medicare, which the edited response is: ‘I’m not going to touch it.’

His final question in this round quickfire of queries is: ‘An unsuspecting woman’s behind?’

‘I will touch that,’ Trump is edited as saying.

And finally he’s asked how he thinks his first 100 days are going: ‘It’s hurting the country.’ 

Searing farewell to Bill O’Reilly, who largely inspired The Colbert Report, after he was fired by Fox News

O’Reilly and Colbert had a contentious relationship. The latter partially based his satirical and titular character of The Colbert Report, his Comedy Central show that ended in 2014, on the former Fox News host.

When Fox News announced in 2017 they would be firing O’Reilly over accusations of sexual harassment, the comedian could not resist poking fun at the news.

‘Bill and I did not see eye-to-eye on anything. I’ve done my share of jokes about him, I also stole his microwave once, it’s a true story, you can look it up,’ Colbert began his monologue.

‘He’s been a guest on this show and I take no pleasure in his downfall. I’m not going sit here and publicly gloat.’

When Fox News announced in 2017 they would be firing O’Reilly over accusations of sexual harassment, the comedian could not resist poking fun at the news

‘I take no pleasure in his downfall. I’m not going sit here and publicly gloat,’ Colbert said as he asks for the cameraman to pan away, presumably to celebrate off-camera

He then asks a member of his staff to take the camera off him ‘for a second.’

The audience is heard cheering, presumably to Colbert reacting off-camera to O’Reilly’s sacking.

When the camera pans back, the host continues: ‘We all saw this coming at us like an old man cornering an intern in the break room.’

But Colbert announces the return of a familiar face: ‘Here’s the thing, I owe a lot to Bill O’Reilly. I spent over nine years playing a character based largely on him and then 12 months of therapy to de-bloviate myself.

‘So tonight, we at The Late Show are proud to issue a statement from Bill O’Reilly’s biggest fan, conservative pundit Stephen Colbert.’

https://youtube.com/watch?v=ZbYpi_WbfkI%3Frel%3D0%26showinfo%3D1%26hl%3Den-US

O’Reilly appeared on The Late Show in 2016. Colbert says he based his character on The Colbert Report on the former Fox News anchor

Colbert then appears onscreen as the character ‘Stephen Colbert.’

‘Shame on you. You failed Bill O’Reilly. You didn’t deserve this great man. All he ever did was have your back — and if you’re a woman, you know, have a go at the front too,’ he says.

The character continues by inviting O’Reilly to join him and former The Daily Show host Jon Stewart to ‘come live in a mountain cabin.’

He ends with ‘stay strong, Papa Bear’ while pretending to hold back tears.

No one is safe, not even his own network, CBS, is immune to being the butt of his jokes

Last year CBS News was slammed after announcing ex-Trump aide Mick Mulvaney had been hired as a paid pundit for the network.

Upon hearing the news, Colbert said it ‘rocked his socks off.’

‘Recently my network has gotten a lot of criticism, much of it from itself, because CBS News hired the ex-president’s former chief of staff Mick Mulvaney to “provide political analysis across the network’s broadcasts and platforms,”’ he said.

‘For more we got to The Late Show’s own media analyst, Stephen Colbert. Stephen, your thoughts?’

The camera then cuts to another angle of Colbert, with the text graphic: ‘Stephen Colbert, Late Show Media Analyst.’

Last year CBS News was slammed after announcing ex-Trump aide Mick Mulvaney had been hired by the network. It had Colbert asking: ‘What the f***?’

‘What the f***?’ is how he simply responds, clearly shocked by the revelation.

‘Back to you, Steve,’ he manages to say before returning to his monologue.

Colbert continues: ‘I for one can’t wait to hear Mulvaney’s trenchant and objective political analysis, considering that back in 2020 he suggested that coronavirus was the “media hoax of the day”… and just days after the election he announced, “if he loses the former president will concede gracefully,” adding: “He’ll fight hard to make sure the results are fair, and in the end he’ll accept the result whatever it is.”

‘Is Mick Mulvaney psychic? Get this man to Vegas. He’s Nostra-dumba**.

‘So obviously, I’m just joking, but why would the Tiffany Network’s venerable news division put this craven toady to a tyrant on their payroll?’

Colbert, citing news reports, said it appeared the network wanted to appeal to Republicans.

‘[CBS is] reworking our programming in the hopes of cosying up to the GOP, so get ready for our new spring lineup: Young QShaman, Bob Restricts the Reproductive Rights of Abishola, and Blue Bloods,’ he quipped.

Colbert ‘bans’ Kanye West after multiple scandals

The host began his monologue back in October last year with a ‘big announcement.’

‘After much though and soul-searching, I, Stephen Colbert, am banning Kanye West, from the Ed Sulllivan Theater,’ Colbert says, feigning solemnity.

He goes on to joke: ‘I have to, I have to, line in the sand. In fact as host of The Late Show, my jurisdiction extends into the northern half of Times Square and I am banning Kanye from coming north of Bubba Gump Shrimp… stay out of Times Square, he’s been creeping out the Elmos and they’ve seen a lot already.

The host began his monologue back in October last year with a ‘big announcement’ before he said he was banning disgraced Kanye West from the Ed Sullivan Theater 

‘I’m also ending all of our high-profile collabs, including but not restricted to our collection of spreadable jams, Strawbeezy Jelleezy,’ Colbert joked

Another parody collaboration, Ye And Phen Sing Fiddler On The Roof

‘I just want to point out that this next part is the courageous part, I’m also ending all of our high-profile collabs, including but not restricted to our collection of spreadable jams, Strawbeezy Jelleezy, and I’ve decided not to release our duets album, Ye And Phen Sing Fiddler On The Roof.

‘I know this has been too long and I have no excuses for why I didn’t do this before except perhaps that he has never been on this show, we have never asked him to be on the show and I am not sure he knows that I have a show.

‘But I had to do it now because I was afraid he would just show up at any moment because that’s what he did yesterday.’

The last part is in reference to West being escorted of Skechers headquarters after turning up to pitch his Yeezy shoes unannounced.

Colbert’s painfully awkward interview with Casey Affeck

In a 2016 clip that made it to air, Colbert calls Affleck out right off the bat for his outfit, with a sarcastic: ‘Thanks for dressing up.’

The interview only went downhill from there, as Colbert said he couldn’t tell whether the casual outfit was the ‘least celebrity thing to do or the most celebrity thing to do.’

Affleck initially tried to play it off, telling Colbert he looked good.

In a 2016 clip that made it to air, Colbert calls Affleck out right off the bat for his outfit, with a sarcastic: ‘Thanks for dressing up’

The comment was only meant to be ‘playful ribbing’ but Affleck did not take it that way

Colbert thanked him before backpedaling, telling him he wasn’t saying he didn’t look good.

‘It was just some playful ribbing,’ Colbert responded.

Perhaps trying to drown out the awkwardness, Affleck reached for a mug on the table to take a drink of water and he asked if it was for him.

‘Let’s find out,’ Colbert joked, before reaching to point out his own mug of water underneath the table.

When Affleck ultimately decided not to take a sip, Colbert called him out saying: ‘It’s just water, did you want something better than water?’

https://youtube.com/watch?v=09H3uJc9fI8%3Frel%3D0%26showinfo%3D1%26hl%3Den-US

Colbert went on to say that Affleck looked like ‘a street corner Jesus’

Sources told DailyMail.com at the time more awkward moments had been cut from the final interview

Affleck passed and the conversation turned back again to his outfit.

‘How long are we going to talk about this?’ Affleck said in frustration.

‘Until I get to my joke,’ Colbert said.

‘Does it always take this long?’ the star asked.

‘It’s not a joke though,’ Colbert said as he went in for the punch line. ‘You really look like a street corner Jesus.’

The joke finally got a laugh from Affleck and the audience, but Colbert still wasn’t done as they were about to start talking about Triple 9.

‘I think we should probably end up fighting at the end of the show – like bare knuckled boxing,’ Colbert stated.

‘I don’t want to do that,’ Affleck said. ‘You want to fight me?’

‘No – it feels like this is where it’s going,’ Colbert responded. ‘I’m wearing glasses so you could probably throw a punch at me.’

Colbert finally let the topic go as he moved on to Affleck’s new movie which comes out on Thursday.

But the awkwardness didn’t end there. While launching into the topic of Affleck’s new film, he openly admitted he only watched an hour and 10 minutes before he had to stop and help his son with a science project.

Sources told DailyMail.com at the time more awkward moments had been cut from the final interview.

‘Royally f***ed up’: Shock over Meghan Markle’s revelations about the royal family in Oprah interview

Perhaps Colbert won Harry over with his scathing assessment of the royal family after Meghan Markle’s 2021 interview with Oprah?

‘Like everyone else I watched Oprah’s bombshell interview with Harry and Meghan, and if you didn’t catch it, let me tell you my lords and ladies, things got real, real quick,’ Colbert started his monologue following the airing of the sit-down.

The video then cuts to a clip of Meghan detailing how she tried to get help for her deteriorating mental health, but was told no, before going to human resources.

It then cuts back to Colbert eating popcorn out of a teapot, saying: ‘Hold up, you’re saying Buckingham Palace has HR? How long has that been around? Because you think someone in human resources might have stepped in to tell Henry VIII that chopping off your wife’s head could be interpreted as a hostile work environment.’

Perhaps Colbert won Harry over with his scathing assessment of the royal family after Meghan Markle’s 2021 interview with Oprah?

Later Colbert discusses what he describes as a ‘troubling conversation’ when Meghan revealed a member of a royal family was concerned about the color of his skin

https://youtube.com/watch?v=avktSv68q6M%3Frel%3D0%26showinfo%3D1%26hl%3Den-US

The Late Show cuts to a clip where Meghan says she didn’t do any research about marrying into the British royal family.

‘What? Let me introduce you to this thing called Google,’ Colbert expresses in disbelief getting out his laptop.

‘It’s full of useful information, it turns out your husband knew Princess Di, that might have been a hint that this would be a rough gig.

He quips: ‘Also while you’re Googling you might want to try the combo: Andrew, island and Epstein. It will give you an idea of what the royal family is okay with.’

Harry and Meghan spoke to Oprah in 2021 about their life inside the royal family

Later Colbert discusses what he describes as a ‘troubling conversation’ when Meghan revealed a member of the royal family was concerned about the color of Archie’s skin.

‘What? And let me just add, huh?’ Colbert reacts.

‘I’m gonna go out on a limb here and say that there is a possibility – just a possibility, mind you – that this medieval selective breeding program might be racist.

‘It’s never good when the British ruling class think that someone’s skin is too dark. They steal their land and make them play cricket.’

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