Stephen Colbert, Donald Trump: The Art of the Funny, Polite, Not Fawning Interview

Stephen Colbert is bringing something new and extraordinarily timely to late-night TV, as he demonstrated in the eagerly awaited “Late Show” appearance by Republican presidential candidate Donald Trump on Tuesday night. Call it the art of the funny, not fawning interview — a chat that conjures laughs without completely sacrificing substance. Without pointing any fingers, some of his competitors should consider taking notes.

Colbert, of course, had a knack for creating amusing exchanges with guests while on “The Colbert Report,” but that was improvising his smug blowhard of a conservative host. In this new venue, he has slowly adapted those skills, punctuated by his discussions this week with two GOP candidates, the other being Ted Cruz on Monday.

In both instances, Colbert managed to actually ask some fairly provocative questions without ever making the exchanges uncomfortable. And when a response from Cruz about gay marriage elicited groans from the crowd, Colbert quickly admonished them, saying, “Guys, however you feel, he’s my guest. Please don’t boo him.”

While it’s unfair and perhaps unnecessary to keep comparing them, Colbert’s visit from Trump stood in stark contrast to the mogul’s appearance on “The Tonight Show” less than two weeks ago, where Jimmy Fallon featured him in a canned segment and then largely giggled his way through their time together at the desk.

By contrast, Colbert had fun with Trump’s brashness (he joked in his opening that he could tell his grandkids he had interviewed “the last President of the United States”), but allowed him to speak his piece. At the same time, he challenged the candidate to state, plainly, after his plunge into birther-ism whether he believes President Obama was born in the U.S., to which Trump simply declined to respond, providing the night’s inevitable headline.

It was, in a way, a win-win for both men. Trump exhibited at least some sense of humor about himself, while still getting in plenty of his talking points. And Colbert didn’t hide his skepticism about some of Trump’s policies — like the proposed wall between the U.S. and Mexico — but kept the conversation light and amusing, not hiding areas of disagreement but being polite about them. Moreover, he doubled down on that by engaging in a detail-oriented discussion about the U.S.-Iran deal with Secretary of Energy Ernest Moniz, before presenting him with a copy of Trump’s signed book.

What seems increasingly clear is that — setting ratings aside — in terms of arriving at a time that maximized his ability to cash in on his unique set of skills, Colbert couldn’t have picked a better moment, with the presidential race, thanks in part to Trump, having become so inexorably tied up in pop culture. And while no one expects a return to the days of Jack Paar or Dick Cavett (who, not incidentally, has wholeheartedly endorsed Colbert), “Late Show” is showing it’s possible to move beyond the typical celebrity guest list and not only generate laughs, but win the next-day news cycle as well.

“I want to thank you for running for president,” Colbert told Trump with mock earnestness. For comics, Trump has clearly been a godsend. Yet even without him, Colbert — in his bid to succeed David Letterman — continues to run his own pretty impressive campaign.

More TV

  • Doctor Who Comic-Con

    'Doctor Who' Star Jodie Whittaker Explains Why Playing the Doctor Is 'Liberating'

    Stephen Colbert is bringing something new and extraordinarily timely to late-night TV, as he demonstrated in the eagerly awaited “Late Show” appearance by Republican presidential candidate Donald Trump on Tuesday night. Call it the art of the funny, not fawning interview — a chat that conjures laughs without completely sacrificing substance. Without pointing any fingers, […]

  • Charmed -- "Pilot"-- Image Number: CMD101c_0494rb.jpg

    ‘Charmed’ Reboot Cast & EPs Talk Original Series, Female Empowerment

    Stephen Colbert is bringing something new and extraordinarily timely to late-night TV, as he demonstrated in the eagerly awaited “Late Show” appearance by Republican presidential candidate Donald Trump on Tuesday night. Call it the art of the funny, not fawning interview — a chat that conjures laughs without completely sacrificing substance. Without pointing any fingers, […]

  • Doctor Who Trailer

    'Doctor Who': Jodie Whittaker Makes Debut as 13th Doctor in Season 11 Trailer

    Stephen Colbert is bringing something new and extraordinarily timely to late-night TV, as he demonstrated in the eagerly awaited “Late Show” appearance by Republican presidential candidate Donald Trump on Tuesday night. Call it the art of the funny, not fawning interview — a chat that conjures laughs without completely sacrificing substance. Without pointing any fingers, […]

  • Watch New Trailer for 'Sons of

    'Sons of Anarchy' Spinoff 'Mayans M.C.' Unveils Intense New Trailer

    Stephen Colbert is bringing something new and extraordinarily timely to late-night TV, as he demonstrated in the eagerly awaited “Late Show” appearance by Republican presidential candidate Donald Trump on Tuesday night. Call it the art of the funny, not fawning interview — a chat that conjures laughs without completely sacrificing substance. Without pointing any fingers, […]

  • Jay Hernandez Comic-Con

    'Magnum P.I.' Cast on the Significance of Reboot Having a Latino Lead

    Stephen Colbert is bringing something new and extraordinarily timely to late-night TV, as he demonstrated in the eagerly awaited “Late Show” appearance by Republican presidential candidate Donald Trump on Tuesday night. Call it the art of the funny, not fawning interview — a chat that conjures laughs without completely sacrificing substance. Without pointing any fingers, […]

  • Lydia Hearst Comic-Con

    Lydia Hearst Defends Husband Chris Hardwick Amid Allegations, Says He'll Be Back on TV Soon

    Stephen Colbert is bringing something new and extraordinarily timely to late-night TV, as he demonstrated in the eagerly awaited “Late Show” appearance by Republican presidential candidate Donald Trump on Tuesday night. Call it the art of the funny, not fawning interview — a chat that conjures laughs without completely sacrificing substance. Without pointing any fingers, […]

  • Disney/ABC TV Group: Peter Rice, Dana

    Disney/ABC TV Group Shakeup: Fox's Peter Rice and Dana Walden Poised to Lead, Ben Sherwood Eyes New Role

    Stephen Colbert is bringing something new and extraordinarily timely to late-night TV, as he demonstrated in the eagerly awaited “Late Show” appearance by Republican presidential candidate Donald Trump on Tuesday night. Call it the art of the funny, not fawning interview — a chat that conjures laughs without completely sacrificing substance. Without pointing any fingers, […]

More From Our Brands

Access exclusive content