Conan O'Brien's 10 Most Hilarious On-Screen Moments

The time Conan had Letterman on

The Moment: David Letterman's first appearance on Late Night with Conan O'Brien (Feb. 28, 1994)

The Gist: When O'Brien took over NBC's 12:30 a.m. time slot from David Letterman in 1993, he got off to a very rocky start — dismissed by audiences, derided by critics and expected by most to be fired before the end of the season. When Letterman returned as a guest during his first season, everything started to change. With his trademark blend of sarcasm and Midwestern charm, Dave gave a vote of confidence for the red-haired upstart. Later, on the night of Letterman's retirement, O'Brien gave a heartfelt speech on his own TBS show about that fateful interview: “On February 28, 1994, David Letterman walked onto my set and blew the doors off the place. It's easily one of the happiest nights of my professional life.”

Where You Can Watch: Late Night and Letterman, on Team Coco

The time Conan rubbed elbows with U.S. presidents

The Moment: The 2013 White House Correspondents’ Dinner (April 27, 2013)

The Gist: After hosting once before in 1995, O'Brien returned to D.C.'s so-called “nerd prom” in 2013, where he enjoyed an easy rapport with President Barack Obama. One of O'Brien's most memorable bits was his comparison of the media to a high school cafeteria: “Fox is the jocks. MSNBC is the nerds. Bloggers are the goths. NPR is the table for kids with peanut allergies. Al Jazeera is the weird foreign exchange student nobody talks to. Print media, you're the poor kid who died sophomore year in a car crash. Cheer up, we dedicate the yearbook to you!” If you want to hear more about the Obama/O'Brien bromance, check out the former president's appearance on Conan's podcast from this May.

Where You Can Watch: The White House Correspondents’ Dinner, on YouTube

The time Conan ran across America

The Moment: Conan runs across America on The Tonight Show (June 1, 2009)

The Gist: In one of the biggest controversies in TV history, O'Brien hosted The Tonight Show for seven months before Jay Leno took the time slot back over in a PR disaster for NBC. O'Brien started his short-lived tenure with a perfectly wacky cold open: In preparing for his debut show, he crosses off a checklist. Build set. Write jokes. Get dressed. Brush teeth. Move to L.A.? He looks out the window at the Chrysler Building and realizes he has made a terrible mistake. When he can't catch a taxi, he simply runs across America — through Amish Country, across the diamond at Wrigley Field, in front of the Gateway Arch, past mountain and desert vistas, under the Las Vegas sign, finally smashing through the gate at Universal Studios.

Where You Can Watch: The Tonight Show, on YouTube

The time Conan drove around with Ice Cube and Kevin Hart

The Moment: Ice Cube and Kevin Hart help a student driver on Conan (Jan. 5, 2016)

The Gist: O'Brien teams up with rapper-actor Ice Cube and comedian Kevin Hart to teach his employee Diana Chang how to drive, and foul-mouthed hilarity ensues. They visit a medical marijuana dispensary, buy a piñata, talk with the cops and pick up chicken from Popeyes. Sure, this might not be the best way to master the rules of the road, but you'll wish you had a spot in the backseat just so you could hang out with this surprisingly perfect comedy trio.

Where You Can Watch: Conan, on YouTube

The time Conan hosted the Emmys

The Moment: The opening of the 58th Primetime Emmy Awards (Aug. 27, 2006)

The Gist: In his second appearance as Emmys host, O'Brien started the show with a bang. Donning a tuxedo and sipping Champagne, he chats with the flight attendant, who asks if he's nervous about the gig. “Nervous?” he replies. “What could possibly go wrong?” Cue a dramatic plane crash, followed by Conan washing ashore on the beach from Lost, where he fashions a blow-dryer out of sticks to mend his hairdo. Soon, he's dropping through the island's infamous hatch and into the office from, well, The Office, before continuing through scenes from 24, House, South Park, and Dateline's "To Catch A Predator" segment. Critics called it one of the best awards show openers in years.

Where You Can Watch: The 58th Primetime Emmy Awards, on YouTube

The time Conan was a country singer

The Moment: Conan records a song in Memphis on Late Night (Oct. 17, 1994)

The Gist: In this vintage clip, a fresh-faced O'Brien heads to Tennessee to record a song about being a lonely talk show host at the legendary Sun Studio. Dressed in a cowboy getup, he pens lyrics like: “I'm just another lonely talk show host, trying to get through to a guest / Though Andy's always there for me, my real sidekick's called loneliness.” He's a surprisingly capable guitarist, a skill he has pulled out of his bag of tricks many times over the years — such as when he challenged actor/rocker Jack Black to a guitar battle. (It's later revealed that Slash from Guns N’ Roses has been helping Conan out from behind the curtain on some of his most impressive improvisations.)

Where You Can Watch: Late Night, on Team Coco

The time Conan was a commencement speaker

The Moment: Conan delivers the 2011 Dartmouth Commencement Address (June 12, 2011)

The Gist: A year after the contentious Tonight Show standoff, O'Brien delivered this poignant — and wickedly funny — graduation speech about disappointment, resilience and reinvention. Of course, he infused it with his usual sense of irreverence: “My first job as your commencement speaker is to illustrate that life is not fair. For instance, you have worked tirelessly for four years to earn the diploma you'll be receiving this weekend. And Dartmouth is giving me the same degree for interviewing the fourth lead in Twilight. Deal with it.”

Where You Can Watch: Dartmouth Commencement Address, on Team Coco

Nicholas DeRenzo is a contributing writer who covers entertainment and travel. Previously he was executive editor of United Airlines’ Hemispheres magazine, and his work has appeared in The New York Times, Condé Nast Traveler, Travel & Leisure, Sunset and New York magazine.