From JFK To Obama, Trump, And Kamala — The Mixed Results of Presidential Candidates in Late-Night TV

Presidential candidates have been reaching out to voters through late-night comedy shows for 64 years, projecting more down-to-earth versions of themselves while mixing in softened, more conversational takes on their stump speeches. Like conventions, debates, and October surprises, late-night appearances are just a part of the cycle now, but are they actually effective at humanizing politicians or swinging votes?

In honor of Kamala Harris’ continuation of this tradition with her recent appearance on The Late Show with Stephen Colbert, it’s worth exploring those questions and seeing how much things have and have not changed in this weird dance between candidates and late-night hosts. 

Candidate John  F. Kennedy visits Jack Paar’s Tonight 

Any list like this needs to acknowledge the firsts. Here, then-candidate John F. Kennedy lasers in on the audience of Jack Paar’s Tonight, answering questions and showcasing the easy charm that won him an election and a legacy as one of America’s smoothest politicians. While 1960 is a very different time with very different rules of the road for political discourse, it all feels just a little familiar, like a congenial and stealthy campaign ad. 

Dick Cavett Grills Vice President Gerald Ford

At the other end of the spectrum, this 1974 Dick Cavett interview is palpably uncomfortable. The legendary host pressed freshly minted Vice President Gerald Ford on whether he thought Richard Nixon had done anything wrong before asking if he would offer Nixon clemency at some point. Ford looks nauseated by the prospect of even having to utter an answer. Eight months later, he would be president. A month after that, he’d pardon Nixon. 

Bill Clinton Briefly Becomes Cool on the Arsenio Hall Show 

Bill Clinton went on the Arsenio Hall Show in 1992 and later won the presidency by virtue of his cool sunglasses and saxman skills. That’s the Cliffs Notes version, but the truth is, that moment is merely an easy-to-remember symbol of Clinton’s sustained outreach to young voters who felt abandoned by old-guard politicians. His charm that shone through in appearances on MTV News is the real reason he won (with an assist from Ross Perot). Self-deprecating and genuinely engaged in Hall’s line of questioning about the Los Angeles riots and racial inequality, Clinton is actually believable when he talks about reconnecting people to the American Dream. Modern politicians should take note when they say the same thing…32 years later. 

Barack Obama Slow Jams the News

Obama sexifiying news reports about student loan interest rates is the spiritual successor to Clinton saxifying Arsenio Hall’s show. It’s probably the second most effective candidate appearance in late-night history. More silly and surprising than funny, it’s a peak pop culture moment for a president who understood the power of viral content and created a brand for himself that is still paying dividends. 

Obama Talks Legacy With Jon Stewart 

The Presidential King of Late-Night, Obama was the first sitting president to guest on one of these shows (Jay Leno’s Tonight Show). He was also everywhere during his two terms, pushing his agenda with appearances on Comedians In Cars Getting Coffee, Between Two Ferns, and the more mainstream late-night shows. But it was on Jon Stewart’s version of The Daily Show where he shined brightest, particularly in a 2015 appearance near the end of both of their (original) runs. 

There’s nothing particularly showy here, just a good conversation with a host who has the audacity to ask real questions (and follow-up questions) to a president who, while typically defensive about his record, seems to also demonstrate some frustration and acknowledge the limits of time and good intentions when running up against bureaucracy.

Biden Shows His Heart To Stephen Colbert 

Joe Biden was not a candidate at the time of this appearance, so it’s a bit of a cheat. But it’s the way we get into the whys of him not running that makes this stand up, and it helped create the base of his supporters in 2020 who felt that Biden really cared about them. Here, Biden is talking about the death of his son Beau in a forum with Colbert, a comic who, like Biden, is deeply attuned to the pain of grief. Whether you like or loathe Biden, if you can still see humanity in politicians (yuge if), then you’ll see it on display here and feel a twist of the heartstrings.

Fallon Sells Out For Silliness with Donald Trump 

In the weeks leading up to the 2016 election, Donald Trump needed to find a way to upend characterizations of him formed by things like what people heard him say with their ears and saw him do with their eyes.

You know, “the Fake News.”

To do this, he submitted to an appearance on Jimmy Fallon’s Tonight Show.

It did not go well.

By way of playful hair tousles and softball questions that gave Trump a platform to air his grievances and peddle his bullshit, Fallon went from politically inconsequential to a lightning rod with a quickness–the embodiment of the “accidentally became important at work and it’s ruining my life” meme. 

He lost viewers and the lead in the late-night wars, and in 2018 seemed bothered by both having done it and by people’s reaction and inability to let it go. In years since, Fallon has had the occasional politician on and told the typical jokes about Trump in his monologue. No one cares. 

Kamala Harris Has a Beer with Colbert In a Yawn-Inducing Late Show

Much anticipated, Harris/Colbert this week felt like a missed opportunity to build on some of the better examples from this list. There were no surprising moments, no realness, and certainly no challenging questions about the war in the Middle East or any other topic. Only the talking points were respected, not the audience, as the two engaged in a painfully awkward beer together, self-satisfaction emanating through both sides of the desk by the end. 

This list reveals, I think two things. First, politicians who can comfortably stand down, be real, and make fun of themselves have an inside track on doing something remarkable for an audience that craves authenticity. Second, our reasoned and funny nightly political observers need to commit more to making people in power feel a little less comfortable more often.