The Best Dark Humor Jokes from Late-Night Hosts

Late-night shows, of course, are marked by darkness just by virtue of the hours that they air. But sometimes, that darkness isn’t just literal — it’s also woven into the jokes and segments of the shows themselves. And so, here are 10 times late-night hosts got as dark as the midnight hour during which they toil on television…

10 Stephen Colbert

“A U.K. Medical practice mistakenly texted its patients that they had ‘aggressive lung cancer’ when they meant to text ‘Merry Christmas.’ Honest mistake — we’ve all done it. Still not as bad as a week later, when they accidentally mailed a letter saying, ‘We have your family in an abandoned shed in the woods. You will never find them— Oops, we meant Happy New Year!’”

9 Conan O’Brien

This segment with a dog trainer and a German shepherd named Ginger takes an unexpectedly dark turn:

8 Seth Meyers

Meyer’s trailer for the most Oscar-worthy movie ever made is definitely scathing, but it’s not exactly wrong either.

7 John Oliver

Oliver turned his thirst for Adam Driver into a brilliant running gag throughout all of 2020, exclaiming all of the increasingly disturbing things he’d like the actor to do to him — e.g., “Step on my throat, you rudely large man,” and “Choke slam me to hell, you nasty shed.” But it all came to a head at the end of the season, when Oliver got a surprise FaceTime call from the man himself.

6 Seth Meyers and Amber Ruffin

From Late Night’s “Jokes Seth Can’t Tell” segment, where Meyers sets up the joke and writers Amber Ruffin and Jenny Hagel tell the punchline for him:

Meyers: A Texas sheriff has placed cardboard cutouts of officers holding radar guns on the side of several roads to deter speeding.
Ruffin: And even one of those managed to shoot a Black guy.

5 Colin Jost

From Weekend Update: “Startup airline Boom Supersonic is hoping to eventually fly passengers anywhere in the world in four hours or less for just a hundred dollars. So, get ready to fly fast and cheap on the only airline named after the sound of an explosion.”

4 Seth Meyers

“DC Comics has put out a new issue titled Batman: Damned #1 that appears to show Bruce Wayne’s penis exposed. I just have to say I’m glad his parents aren’t alive to see this.”

3 Conan O’Brien

Hunter S. Thompson refused to come to the studio for an interview, and instead invited O’Brien to shoot guns and drink. The result is one of the craziest “interviews” in late-night history.

2 Michael Che

From Weekend Update: “The CIA is marking its 75th anniversary by launching a podcast, and because it’s the CIA, they’re launching it directly into an Afghani wedding.”