Gen Z has discovered why Conan O’Brien was the best late-night TV host of all time

Who is Conan O’Brien? It’s a question that, until last week, many Zoomers and Gen Alphas probably wouldn’t have been able to answer, at least not in detail.

Now, thanks to an episode of Hot Ones – a YouTube series in which celebrities answer questions while eating spicy hot wings – Gen Z is learning a lot more about O’Brien, former The Simpsons writer and host of late night talk show Conan.

Conan O’Brien seems to have just gotten Gen Z’s attention, but he was around long before Hot Ones.Credit: First We Feast/YouTube

During his appearance, which was timed to promote his new travel show, Conan O’Brien Must Go, the comedian transformed into what can be described as an unhinged goblin-man. He guzzled hot sauce from the bottle, spilled milk over his clothes and filled his pockets with half-eaten chicken bones. It was chaotic, unfiltered and nonsensical. In other words, it was Gen Z comedy gold.

The popularity of the clip, and Conan’s other recent media appearances, has led to new fans delving into the archives of his career, discovering his SNL days in the late 1980s, his time writing for The Simpsons, and his first talk show, Late Night with Conan O’Brien.

Here are five of O’Brien’s best moments to date, including this trip to Australia.

Conan goes apple-picking with Mr T

Sometimes, the key to comedy success is simply combining two disparate things. O’Brien mastered this in 2000, when he went apple-picking with Mr. T (The A-Team) to celebrate the arrival of autumn.

Pairing an actor known for his macho bravado with a traditionally wholesome activity was inevitably going to be funny – who wouldn’t laugh at Mr-T shouting at apples to try to get them to fall down?

“I pity the apple that don’t fall down,” O’Brien says.

Conan’s controversial crooner

In 2005, ghost crooner Artie Kendall was introduced to O’Brien’s show. In his soothing 1930s style, he sang incredibly offensive material, once again subverting expectations by pairing two seemingly incompatible things.

Nothing was off-limits – women’s ability to vote, child labour, the Irish. It pushed boundaries without pushing buttons.

Conan in the year 2000

“In the Year 2000” became a regular segment on Conan’s talk show, but one of the best has to be the Larry King special in 2005. The legendary pair prophesize what will happen in the “future”, aka the year 2000, despite it already being 2005.

“Parents will stop telling kids about the birds and the bees when the birds and the bees release a series of bondage porno films,” King says. It’s ludicrous while also sharp-witted and occasionally astute. Jumping from punchline to punchline also offered a simple formula that worked regardless of the guest celebrity.

Conan hosts the Emmys

O’Brien’s opener for the 58th Primetime Emmys is largely considered one of the best in Emmys history, even beating the comedian’s first time hosting in 2002.

Referencing shows like Lost, The Office and House, O’Brien doesn’t shy away from self-deprecatory humour, at one point having his body described by Dr. House as “awkwardly proportioned” and ending the segment by being exposed as a sexual predator in a spoof of Dateline.

Conan goes Down Under

In 2019, O’Brien aired his Conan Without Borders Australia special, which quickly became many Australians’ favourite Conan moment. He learned slang like “budgie smugglers”, kicked the ball around with the Sydney Swans, and becomes a Bondi Beach lifeguard.

There will always be something humorous about watching very American people adapt to culture down under, but O’Brien’s sarcasm and his willingness to look dumb makes his visit a particularly memorable crossover.

Conan O’Brien Must Go will be available to stream on Binge on April 18. His podcast, Conan O’Brien Needs a Friend, is available wherever you get your podcasts.

Find out the next TV, streaming series and movies to add to your must-sees. Get The Watchlist delivered every Thursday.