Late Night & the Endless Election: Top 10 Late Night Political Moments

Liam Cummins
4 min readJan 3, 2021


Published 06/01/2021, updated 07/01/2021

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Late Night has always been close to the edge, but over the past 5 years its seemed America has been too. Welcome to liamcumminsuk, and today we’re looking at the top 10 political late night moments.

For this list, we’re looking at moments from classic late night which sparked a conversation or brought some hope.

Copyright: Vanity Fair

#10: O’Brien on O’Bama

“Late Night with Conan O’Brien”

Barack Obama on “Late Night with Conan O’Brien”

Before Barack Obama went on to win the presidency, he visited the now elder statesmen Conan O’Brien in 2006. Here he dismissed his running for president, but introduced himself to the next generation of voters.

#9: Austerity in America

“Late Show with David Letterman”

David Cameron on “Late Show with David Letterman”

Former British prime minister David Cameron got the world speaking when he visited late night legend David Letterman’s show in 2011. Here he failed a quiz about his own country but played a smooth character.

#8: Boris the Author

“Late Show with David Letterman”

Boris Johnson on “Late Show with David Letterman”

Another British prime minister visiting Letterman, but back then he was simply Boris. Playing his usual charade, Boris won over audiences in America, but dismissed claims he would ever be Prime Minister, ah simpler times.

#7: No He Can’t

“The Late Show with Stephen Colbert”

Joe Biden on “The Late Show with Stephen Colbert”

2016 was a year many would prefer to forget, but before Hillary faced Donald Trump, it was Joe Biden who was expected to take the crown. Biden’s frankness in this clip created a heartwarming piece of television.

#6: The Hair Ruffle

“The Tonight Show with Jimmy Fallon”

Donald Trump on “The Tonight Show with Jimmy Fallon”

Also from 2016, this is just one of Fallon’s faux par during the 2016 election when Donald Trump visited Fallon numerous times. The host just couldn’t resist focusing on the big issues — whether or not Trump’s hair was real. Safe to say, this landed him in hot water.

#5: End of the Road

“The Late Show with Stephen Colbert”

Colbert signs off 2016 election on “The Late Show with Stephen Colbert”

At points in 2016, Colbert seemed to be the voice of the nation but even he was stumped when Donald Trump won the election. The script was thrown out but the Late Show host delivered a sharp monologue. This goes at number 5 for its silent strength, rather than its bite.

#4: A New Light


O’Brien signs off 2016 election on “Conan”

While Colbert grieved, Conan reassured the nation. Moving the conversation on to the beauty of democracy, and the historical context. The Harvard graduate sure does know his stuff and is a master at aiding the country in a crises.

#3: He’s Back

“The Late Show with Stephen Colbert”

John Stewart on “The Late Show with Stephen Colbert”

John Stewart was the host of the Daily Show for over a decade, and was once the voice of the young generation. In this list however, only the Late Night shows count, so good thing Stewart took time to visit his friend Stephen Colbert. Here he delivered a biting rant to the camera around Fox News’ backing of Trump, and the nation backed him all the way.

#2: Jacinda, who?

“The Late Show with Stephen Colbert”

Jacinda Ardern on “The Late Show with Stephen Colbert”

You can see a trend here, Colbert seems to have cracked the political circus.

In 2018 at the height of Donald Trump’s term New Zealand delivered a liberal leader that even America admired. Jacinda Arden proved to the world she was a capable leader with no concern for populism. Now with Covid it’s hard to remember a time when we all didn’t know her name.

Honourable mention: The Darkest Day

“The Late Show with Stephen Colbert”

Colbert talks through his thoughts on the 2021 storming of the United States Capitol

Colbert knows how to lead America at times when it seems leaderless. The coup on the Capitol by domestic terrorists shocked the world, Colbert was angry. He didn't offer hope and the laughs were hollow. This was beyond any attack seen before, it was an attack on the basic right to vote initiated by the man elected to defend it. This can’t make the list, the dark lasting undertones mean this can never be a best moment. But hopeful & different days are ahead.

#1: End of the Night

“The Late Show with Stephen Colbert”

Colbert signs off 2020 election on “The Late Show with Stephen Colbert”

After 3 years of all the Late Night shows grilling the Trump administration, even the viewers were keen to see it end. So with the triumphant return of Joe Biden, Colbert finally got his win. For audience members they were waiting for Colbert’s first word on the victory.

This is top of the list because it’s the beginning of a new chapter for late night, hopefully one wrapped up with joy.

Do you agree with our list? What’s your favourite Late Night moment? Vote below…

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Liam Cummins

Sharing wealth, eating crumpets & watching housewives.