It was sad to see Conan O’Brien end his 28-year run on late night TV with plans to host a weekly variety show on HBO Max. On the bright side, the extra time does give the 58-year-old, four-time Emmy winner and podcaster more time to hone his acting skills, which he has presented before with cameos in several movies, TV shows, and even video games (namely Halo 4 and Death Stranding, to name a few). Of course, he plays himself in a lot of these appearances, like on 30 Rock, The Office, Family Guy, and his acting debut, which was also his first animated voice acting role.
The Simpsons (Conan O’Brien)
One of Conan O’Brien’s earliest gigs was writing for The Simpsons, which makes his cameo on the long-running animated series (just a year after he took over Late Night on NBC) all the more special. In a Season 5 episode in which Bart (Nancy Cartwright) becomes famous by uttering “I didn’t do it” on Krusty the Clown’s show, he lands a spot as Conan’s guest and prepares for it by studying some intelligent, anecdotal information. However, all Conan wants to hear is Bart’s famous line.
Futurama (Conan O’Brien)
Years later, Conan O’Brien would re-team with The Simpsons co-creator Matt Groening on his second most popular animated series, Futurama, for another vocal cameo as himself. However, as per tradition with the 31st-set Century comedy, only O’Brien’s head (and the head of Max Weinberg) appear in this Season 2 holiday episode because, as he explains to Bender during a set at the Catskill’s Lodge, he lost his “freakishly long legs in the war of 2012.”
Andy Richter Controls The Universe (Freddy Pickering)
One of Conan O’Brien’s first collaborations with Andy Richter after his sidekick left Late Night (before coming back for Conan’s Tonight Show and TBS stints) was on Season 2 of the comedian’s own sitcom, Andy Richter Controls the Universe. In one of his rare TV appearances as someone other than himself, the talk show host turns up the crazy to play the overly narcissistic Freddy Pickering - the wealthy heir to Andy’s company who makes work a nightmare for his colleagues and tempts Andy with the exaggeratedly luxurious life of a manager’s position.
30 Rock (Conan O’Brien)
Before Conan O’Brien wrote for The Simpsons, he wrote (and even appeared in a few sketches) for Saturday Night Live, which makes his dual cameos on 30 Rock - a parody of the behind-the-scenes antics of an SNL-style show starring and created by an SNL alum - all the more special. Both of his appearances (and anytime he is even mentioned on the irreverent NBC sitcom) reference a recurring joke suggesting that O’Brien and Tina Fey’s character Liz Lemon were once romantically involved.
Bewitched (Conan O’Brien)
Conan O’Brien also made a notable cameo as himself alongside another beloved former Saturday Night Live cast member in Bewitched - the 2005 comedy about a disgraced actor (Will Ferrell) who unwittingly casts an actual witch (Nicole Kidman) as his wife on a reboot of the magical sitcom from the 1960s. Spooked to learn he has fallen in love with a real sorceress, Ferrell’s character, Jack Wyatt, later dreams that he makes an appearance on Late Night completely nude (as seen from a green room monitor), much to O’Brien’s horrified surprise.
The Office (Conan O’Brien)
Also appearing in that Bewitched scene as a meta take on the Uncle Arthur character is Steve Carell, whose better known role from The Office cast, Michael Scott, once missed out on an opportunity to meet Conan O’Brien during a visit to Rockefeller Center in Season 2. Michael chases after someone he wrongfully assumes is Tina Fey, only to learn from the documentary crew that O’Brien was walking right the past cameras at that exact moment.
How I Met Your Mother (Bar Patron)
Conan O’Brien also made a blink-and-you-miss-it sitcom cameo on How I Met Your Mother in the Season 7 episode “No Pressure,” as a random guy at MacLaren’s Pub. The host had previously mentioned, when HIMYM cast member Neil Patrick Harris was on his TBS program, that he won a walk-on role on the show at a charity benefit and opted for an uncredited background appearance instead of the chance to formally interact with the main characters. It’s actually much funnier that way, in retrospect.
The LEGO Batman Movie (The Riddler)
You also might not have noticed when Conan O’Brien lent his voice to The LEGO Batman Movie in 2017. He does a pretty good job altering his voice (and laugh) in an especially goofy fashion to play one of the more enigmatic (and red-haired) Batman villains, The Riddler. This would not be O’Brien’s only visit to Gotham City, however.
Batman: The Dark Knight Returns, Part 2 (David Endochrine)
Before voicing The Ridder in The LEGO Batman Movie and voicing himself in the video game LEGO Batman 3: Beyond Gotham, in 2013, Conan O’Brien voiced a character in the second-half of the animated adaptation of Batman: The Dark Knight Returns that could not be more perfect for him: a late night talk show host. Even though Frank Miller obviously modeled David Endochrine (who makes the mistake of inviting the seemingly reformed Joker onto his show) after David Letterman in his original 1986 graphic novel, it is fun and fitting to see his Late Night successor fill the role.
The Mitchells Vs The Machines (Glaxxon 5000)
Conan O’Brien got to play more on the side of villainy in the Netflix original comedy The Mitchells vs the Machines, in which he gives one of his most recent vocal performances as Glaxxon 5000 in 2021. The well-dressed robot makes for a very personable (yet foreboding) host of an informative video the titular family sees as they unwittingly board one of many rockets that intend to eliminate humans from the face of the Earth.
Sharktopus Vs. Pteracuda (Conan O’Brien)
I believe that we have saved the absolute best for last on our list of hilarious Conan O’Brien cameos with his much celebrated role in Sharktopus vs. Pteracuda - a Syfy B-movie of the week from 2014. At first it seems that the host is playing some random rich, ascot-wearing douchebag until his enjoyment of the beach is interrupted by some volleyball players whom he then scolds, using his real name and referring to himself as an icon. His tirade is interrupted by Sharktopus, which shoves its tentacle up O’Brien’s rear-end and out his mouth before taking his head clean off, which the volleyball players then use to finish their game.
As some who faithfully keeps tracks of any and all upcoming Conan O’Brien TV shows, I really hope we have not seen the last of the talk show host’s acting career, whether he is playing some eccentric character in the Batman movies or some eccentric version of himself on TV.
