As of the time of writing, comedian and television host Conan O‘Brien is age 61. Statistically, he’s close to the end of his natural lifespan. To the generation that grew up alongside him throughout the various cable networks that broadcasted his shows in the Philippines, it’s a grim reminder that the needle on his cultural marker has moved. I count myself among those who no longer see him as the disruptive late-night comedy maverick, but an elder statesman of comedy.
There is an audience that knows him more for his podcasts and viral clips than for shows like Late Night with Conan O’Brien or The Tonight Show with Conan O’Brien (he was even a sketch comedy writer for Saturday Night Live). After all, Conan O’Brien Needs a Fan has featured more than its fair share of Filipino guests. Though “goofy dad” seems to be a more appropriate descriptor — familiar and comforting, jokes are still landing even if the edges have dulled. With his gig hosting this year’s Academy Awards poised to dot the I’s on this shift, it feels appropriate to roll out a requisite list of Conan moments to show how resonant his comedy and hosting have endured over the years.
Here they are, in no particular order.
The Best ‘Hot Ones’ Episode of All-Time
The most recent of O’Brien’s moments, it’s a great introduction to the full spectrum of O’Brien’s comedy. In a guest spot that became increasingly unhinged as the interview went on, it’s a gut-busting reminder to see how far O’Brien will go to commit to a bit. Rolling out Doctor Arroyo only serves to show that O’Brien’s comedy works best when he’s surrounded by off-beat characters and straight men. He was also medically compromised after the interview, which is icing on the cake.
Conan > carpool karaoke
Arguably the spot that defined his TBS run online, the driver’s license segment is the perfect storm of elements. From his down-for-anything staff member Diana Chang, to Cube and Kevin Hart being perfect foils to O’Brien’s dopey straight man and the inadvertent quest for Popeye’s chicken, it’s a zany road trip movie compressed into a light night segment.
Death Stranding
Appearing in Hideo Kojima’s star-studded video game Death Stranding was the inevitable culmination of O’Brien’s “Clueless Gamer” segments. Playing a bunker-dwelling NPC who married a cosplayer, O’Brien’s wandering MC bequeaths protagonist Sam Porter Bridges a wearable item called the “Otter Hood.” It was a surprise cameo that was both baffling and fitting for O’Brien’s and Kojima’s brands of weird.
51 Seconds of Madness
During the writer’s strike between 2007 and 2008, O’Brien kept the show going on sheer comedy gumption alone. That entire period of Late Night with Conan O’Brien can easily make several lists a couple of times over for the sheer audacity of its skits and segments. While most were throw-it-against-the-wall-and-see-what-sticks type of madcap comedy, it’s the running jokes that resonated the most. O’Brien eventually beating the record of spinning his wedding ring is the perfect encapsulation of that period, turning a throwaway bit into something that everyone became invested in week after week. It’s also a reminder that O’Brien takes care of his own, and does it in a way only he can.
Norm Macdonald & Courtney Thorne-Smith
Norm Macdonald has been a staple guest on O’Brien’s shows for a long time. O’Brien is always eager to give Macdonald a wide berth, and willingly be his punching bag. The purest distillation of this dynamic happens when the Melrose Place actress Courtney Thorne-Smith stops by to promote her movie Chairman of the Bored with comedian and actor Carrot Top. Macdonald inserts himself into the interview, much to O’Brien’s chagrin, and tears into Throne-Smith’s leading man. It’s a delight to see O’Brien manage both his guests because it all goes comedically awry.
Old Timey Baseball
This is one of the best segments of the Late Night with Conan O’Brien era, with the DNA for the material eventually evolving into Conan O’Brien Must Go. This makes the list because of O’Brien’s chemistry with Nell Del Giudice, the period actor in the segment. Del Giudice’s commitment to her bit throws O’Brien off his game, and it’s a delight to see him match her energy as the segment goes on. O’Brien wears the “Old Timey” title well, leaning hard on the mannerisms and slang to really crank everything up to eleven.
Farewell Show
Speaking of the needle moving, this was the big one. With an entire generation cheering him on, O’Brien finally landed his dream gig hosting The Tonight Show. Tragically short-lived due to a whirlwind of factors, O’Brien’s heartfelt sendoff speech truly felt like the end of an era. While he says many goodbyes before finally retiring from the late-night hosting format, it’s this one that hits the hardest- sad but eternally optimistic.
Songwriting for David Bowie
O’Brien is at his best when the unexpected happens. Bringing attention to O’Brien musicality, the guest spot has singer-songwriter David Bowie performing a song O’Brien wrote. When O’Brien’s G string breaks, the host and guest relationship dissolves, and the spot becomes two personalities riffing off of each other. That obscure videogame Omikron The Nomad Soul makes an appearance just sweetens the deal.
Grammar-Off with Jennifer Garner
While it’s great that O’Brien got his flowers for his comedy, it is easy to forget how brilliant of a host he is. When actress Jennifer Garner calls him out for using the word “snuck,” O’Brien immediately self-deprecates and acquiesces to its non-existence. O’Brien is only biding his time, though. While he mounts Garner’s comeuppance, it’s not mean-spirited or ill-intentioned. O’Brien mounts it in such a way that she’s not embarrassed, proving he’s one of the best to ever do it.
