It’s not quite clear how Conan’s next comedic foray will pan out; the comedian is set to host a weekly variety series on HBO Max but details are scarce. Regardless, there’s ample reason to be excited about Conan’s next steps given that he and his writing staff have produced countless memorable interviews and recurring and one-off bits over the decades. Conan has hosted three late-night shows spanning thousands of episodes since 1993 and much of his material has been digitally preserved and is neatly categorized on YouTube and Conan’s own website. Conan has been behind countless memorable interviews, one-off and recurring bits, and other hilarious clips throughout the last quarter century of late night TV. It’s a lot to take in, so here’s but a sampling of some of Conan’s greatest bits over the years:
Old-Time Baseball
Conan’s 2004 sojourn to a New York park to play old-timey baseball is one of his most well-known clips and a personal favorite of the comedian. Conan referred to the clip as his favorite during his final “Late Night” episode; at the time he stated that, “I’ve told the staff, ‘When I leave this earth, at the funeral, just show this because this pretty much says what I’m all about.’”
Triumph the Insult Comic Dog at the “Attack of the Clones” Premiere
Triumph the Insult Comic Dog, puppeteered and voiced by Robert Smigel, has appeared in a variety of bits on Conan’s shows over the years. The character’s insult comedy at a premiere of “Star Wars: Attack of the Clones” in 2002 is by far its most famous appearance, and for good reason. Simply put, the segment is 11 minutes of nonstop hits —“You look like some kind of super nerd! It looks like you were built in a laboratory out of parts from lesser nerds!” Smigel doesn’t miss a beat when interacting with the superfans outside the theater who are surprisingly good-natured despite the insults being lobbed their way.
Jordan Schlansky’s Elitist Espresso Machine
Some of Conan’s most popular recurring bits center around the comedian’s interactions with his show’s employees, particularly those including Jordan Schlansky, Conan’s famously eccentric associate producer. The segment, centered on a $500 espresso machine, is the perfect encapsulation of why Schlansky is one of Conan’s most popular employees to spotlight:
Ice Cube, Kevin Hart, Conan, and a Student Driver
It’s Ice Cube, Kevin Hart, and Conan O’Brien, an obvious recipe for success and made for Conan’s most-watched comedy video on YouTube (it’s his channel’s second most-watched video, behind Disturbed’s performance of “The Sound of Silence” in 2016.)
Steven Yeun and Conan Visit a Korean Spa
Conan is hardly the only celebrity who has built a public image as a goofy and awkward everyman, but he pulls the shtick off better than practically all of his contemporaries. This is best exemplified in Conan’s myriad segments where he ventures outside the studio to participate in all sorts of activities, such as when he joined “The Walking Dead” and “Invincible” star Steven Yeun for a hysterical trip to a Korean spa, where the duo strip and Conan wails in over-the-top agony while getting a full body scrub and submerging himself in freezing water (well, 61 degree water, close enough).
Conan Visits Haiti
Conan has created several “Conan Without Borders” episodes where he travels to other countries to riff with people on the streets and learn about their culture. Conan’s trip to Haiti was inspired by former president Donald Trump referring to the country as a “shithole,” and Conan’s episode-length response made for one of his most heartfelt (and still very funny) international segments. Conan’s jokes with a local musician score plenty of laughs, as does a genuinely touching scene where Conan eventually wins over a crowd of locals who are initially skeptical of an American traveling to their country with a camera crew.
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