How Late-Night TV Has Loved Lampooning Donald Trump


Late-night TV is going live again after tonight’s third and final presidential debate, in which Donald Trump is expected to go full Drain the Swamp, while Hillary Clinton affects warmth and transparency.

Late night shows have played a very different role this election cycle than in cycles past. Gentle political comedy is out, particularly in this later, general election period, as Jimmy Fallon learned when he mussed Donald Trump’s hair on The Tonight Show. Blazing, mostly Trump-bashing, editorializing is in, among the many shows now hosted and written by Daily Show alums, and a former Saturday Night Live Weekend Update writer-anchor.

Trump bashing is a real Sophie’s Choice, as Stephen Colbert has noted. If the first presidential candidate to generate his own comedy gets elected, it’s the greatest gift for late-night TV. On the other hand, if Trump is elected (a path that’s looking increasingly remote with this morning’s new polling), it may not be so good for the country, Colbert has acknowledged.

Walking up to tonight’s third and final debate, take a look at some of late-night’s biggest swings at Trump, the presidential candidate that reality-TV made:

Jimmy Kimmel Reads Bedtime Stories To Trump

“The Dr. Seuss parody was my idea,” Jimmy Kimmel says of Trump’s first visit to his ABC late-night show as a presidential candidate.

“I was reading ‘Oh The Places You’ll Go’ to my daughter, over and over, every single night.” That got Kimmel thinking you could say most anything to Trump, so long as the word “Winner” was in it. Kimmel and his writers began working on Winners Aren’t Losers, before they even knew they could book Trump. “I figured he’d be on the show eventually and wanted to have it ready when he did. We wanted it to rhyme well, and for the drawings to look like a real children’s book.”

Trump did not know about the book in advance of his Jimmy Kimmel Live appearance. “Generally we don’t run questions or anything of that sort by politicians,” Kimmel says. “We always do with celebrities, but never politicians. That’s part of why it’s a lot more fun to interview somebody that’s running for office.”

The day of Trump’s guest gig, Kimmel held the book for the end of the interview, because “reading a book for three minutes is a long chunk of an interview,” especially if it’s not well-received by the guest, the late-night veteran notes. After asking Trump some pretty biting questions about his campaign promises to build that wall, etc., Kimmel sent a canary down into the coal mine, asking Trump if he was aware the screenwriter of Back To The Future Part II had based his bully Biff Tannen character on Trump.

“I love that!” Trump beamed. “Where’s my cut? I want a cut!”

Taking that for an all-clear, Kimmel introduced the book, which Trump predicted would be a bestseller, after hearing the opening:

Winners aren’t losers. They’re winners – like me!

A loser’s a loser. Which one will you be?

Winners do deals and winners get rich!

While sad little losers just sit there and bitch.

Kimmel to this day is not sure if Trump got the dig, or simply did not care. “It’s one of the great mysteries of Donald Trump. I’m not sure he knew the Comedy Central roast was a roast,” Kimmel jokes. “The headline is what’s most important to him in all cases. Any time the title of the book is ‘Winner’s Aren’t Losers,’ that’s where it stops for him.”

Stephen Colbert Diagrams Trump’s Orlando Attack Response

Colbert clobbers Trump at the top of his Late Show nearly every night, while still trying to book him on the show with taunts, calling the candidate a coward and a chicken for declining Late Show‘s invitations to appear. The New York Times‘ former media reporter Bill Carter recently pronounced, speaking for us all, Colbert’s show to be much improved since he’s cut loose with election-cycle commentary, reminiscent of his Colbert Report self. His Trumpiness takedown of the candidate on Late Show remains the best explanation yet televised of the improbable success of the candidate’s White House run to date. But maybe most impactful, Colbert’s episode after the Orlando nightclub shooting, in which he diagrammed how Trump used the national tragedy to score political points. Cooked up in the writers room, the former CBS News exec who now show-runs the program first saw the comedy bit in the re-write room. And the CBS Decency Police, who were given a heads up, sent up no red flag, to the happy surprise of at least this TV columnist and the 8 million who have viewed it to date:

Samantha Bee Explains Brexit To Undecided Voters

Samantha Bee’s showrunner Jo Miller hesitates when asked what segment on her show she thought rose to the top, Trump-wise, describing Full Frontal as a “running narrative” in which the  “conversation about Trump runs through our show.” But she points to the ‘Oh Shit Brexit’ episode that premiered on TBS right after UK’s Brexit vote to leave the EU. “This is the one where we explained why it’s not enough for Trump to lose, it has to be a 50-state ass-whipping, a repudiation of Trumpism,” Miller explains:

Seth Meyers Offers Trump Lead In ‘Chicago President’

Meyers has carved out his own Taunt Trump niche in late-night. He famously banned Trump from the show Meyers acknowledged Trump has never shown any interest in appearing on, after Trump had banned some reporters from his rallies. That was followed by an episode in which Meyers tempted Trump to drop out of the race with an offer to star as Pretend POTUS in a new NBC primetime drama. NBC execs with whom we spoke insist Meyers’ A Closer Look segments are not intended as a counterweight to Fallon’s candidate-friendly late-night bits, rather are an extension of Meyer’s well honed brand:

Trevor Noah And Lindsey Graham Talk Trump

What happens when you throw a busted presidential candidate with a caustic wit, an imploding political party and nothing to lose into a late night-TV show? If it’s South Carolina Sen. Lindsey Graham visiting Trevor Noah’s The Daily Show, he blows the place up.

Noah set up Graham’s appearance, during the primary election cycle, with a segment in which he demonstrated how the Republican Party’s relationship with Trump actually is a rom-com storyline: The party thinks it hates Trump, but he’s actually the man of its dreams. After what remain the most gob-smacking late-night interview of this election cycle, the two men played Compliment Donald Trump Pool:

and here they are playing pool:

Jimmy Fallon Tousles Trump’s Tresses

Although Jimmy Fallon gets rave reviews for his impersonation of Trump on Tonight Show, especially when Trump and Hillary Clinton paid primary-season visits, his more recent Trump hair-mussing bit made headlines and triggered a national conversation about the responsibility, or not, of late-night hosts when interviewing the polarizing candidate.

Most of Fallon’s late-night colleagues defended his choice. Colbert said the gag would have been a terrible mis-step for his show, but it was true to Fallon’s program. Kimmel speculated that Fallon’s gag would not have caused such a kerfuffle had he tousled Trump’s tresses six months earlier, when TV critics and political pundits were far less undie-bunched about Trump’s shot at the White House. But one late-night exec, who asked not to be named, called it a “misstep” and a “5-minute interview to get the [hair-messing] punchline,” while another called it “awful” and put Fallon “squarely into” company of Lorne Michaels and Jeff Zucker among TV industry notables who helped Trump get this close to the White House:

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