11. Pale Force
This sketch was created by standup comedian Jim Gaffigan who had many appearances on the show. The writing was done by Jim Gaffigan and Paul Noth. The art, animation, and music for the cartoon were done by Paul Noth. All of the voice acting was done by Jim Gaffigan. Jim Gaffigan would show up on one of Conan’s shows and do a standup routine. He would then introduce a segment of the cartoon. The cartoon depicts Jim and Conan as superheroes who use their pale skin to fight crime. Inevitably, Gaffigan is depicted as a lantern-jawed, brave ladies’ man. Conan is depicted as a frail effeminate scaredy cat with a high-pitched voice who often pisses his pants. Their main villain was Eartha Kitt who was known as Lady Bronze on the show. (Again, Gaffigan did all the voices). The episode would end and Conan would be laughing incredulously, complaining about how he is depicted.
10. The Walker Texas Ranger Lever
This was a very simple bit developed by Conan and his staff. The idea was that NBC had acquired Universal back in 2004 and thus had acquired the rights to Walker Texas Ranger. This gave Conan the ability to show clips of the show “royalty free”. The show had apparently been a lowkey hit at one point but it was definitely goofy. Every time Conan pulled a lever, an out-of-context clip of Walker Texas Ranger would play. The staff did a really great job at picking the strangest clips. Conan would gleefully pull the lever when he felt the show was slowing down. It could have been any show but using clips from a production company known for putting out campy material was a great choice. Also, Chuck Norris’ career was on the decline and action movies were making a cultural shift. Conan’s maniacal face as he pulled the lever was often the best part.
9. Frankenstein Wastes a Minute of Our Time
These sketches were most likely written by Brian Stack although most of the writing was dealing with logistics. It could be that this sketch was also inspired by NBC’s acquisition of Universal which includes their version of the Frankenstein story. Brian Stack portrayed Frankenstein who would randomly interrupt Conan in an excited state. Frankenstein never talked but he would gleefully beckon for the cameraman to follow him. Conan would give the go-ahead and would narrate the action as the camera followed Frankenstein. Frankenstein would travel backstage of the studio and eventually arrive at something really interesting. He would then ignore it and direct the camera to something mundane, excitedly celebrating it. Conan would always be very curious at the start but would berate the monster when he realized that, once again, the big galoot had wasted their time. I also feel like the title was designed to annoy pedants who often “um actually” about the monster’s name.
8. Mick Ferguson, The Guy Who’s Awfully Proud of his Bullet Proof Legs
This sketch premise was written by staff writer Brian McCann during the Late Night days. Brian McCann played the titular Mick Ferguson. The premise was that vaudevillian singer/dancer Mick Ferguson would come out to do a routine about his bullet-proof legs. Inevitably, somebody would somehow shoot him in the heart. He would return several times, each time tasking Conan with making sure he does not get shot. Conan does not do a good job at this mostly because Conan does not seem to care very much. The fun of this sketch is in the variations. The sketch tends to get stranger and stranger as every safeguard fails. These were definitely born out of the years when Conan was left unattended as the network did not seem to actually watch his show.
7. Andy Richter is Crazy
These sketches were most likely written by Andy Richter himself as Andy was an integral part of the writing staff during his tenure on all three shows. It was important to both Andy and Conan that Andy was more than just Conan’s sidekick. Over the years, Andy created a complex and interesting character and that character was insane. His reactions to Conan’s monologues often spiraled into sketches where Andy could show exactly who he is. No two sketches were the same but the recurring glimpses into Andy’s world were always fascinating. A lot of the humor came from how surreal and absurd the sketches were coupled with Richter playing it straight.
6. Artie Kendall the Ghost Crooner
This sketch premise was written by staff writer/performer Brian Stack. Brian Stack performs the character of Artie Kendall. The premise was inspired by the history of the studio where Late Night With Conan O’Brien was filmed. The same studios were used to record and broadcast NBC radio long before there was television. They were also apparently inspired by rumors that radio and film legend Bob Hope had a dark side that he never showed in public. The sketch always begins as Artie Kendall’s voice is heard before he materializes near Conan’s desk. Artie is the ghost of a crooner from the thirties. Conan is amazed and excited to have a piece of history show up and encourages Artie to sing. Artie starts singing short songs that espouse his sexism, racism, and/or classism. After each song, Conan talks about how terrible the lyrics were, getting angrier after each song. This causes Artie to utter a remark about Conan’s “hot Irish temper” and then he sings a song full of the worst Irish stereotypes. This finally causes Conan to shout at him to go. The humor comes from the audacity of Artie’s lyrics coupled with Conan’s outrage and the audience betraying Conan by cheering Artie’s songs.
5. Andy’s Little Sister Stacy
This sketch premise was originally written by staff writer Brian Stack. (It was apparently his first sketch for the show). Amy Poehler plays Andy’s sister Stacy who interacts with Andy Richter and Conan O’Brien. The premise was that Stacy would make an impromptu visit to the show and would somehow make herself known out in the audience. Andy would acknowledge his sister and Conan would welcome her to the show. During her visit, Andy would usually mention her crush on Conan. Conan would be flattered but comment that he was too old for her, already had a girlfriend, liked her as a friend, and so on. Stacy would lose her mind with anger that Conan would not acknowledge her love for him in long fiery speeches. She would also roast her brother for exposing her feelings in the first place. Poehler was so great as this character and a lot of the humor came from the awkwardness from Stacy and Conan.
4. Paul Rudd Shows A Clip From His Work
Paul Rudd has been a guest on Conan’s various shows since 2004 when he was promoting the final season of Friends on which Rudd was a guest star. For all intents and purposes, this bit was conceived by Paul Rudd without Conan’s involvement. That is how they have chosen to portray it and that is how I wish to see it. The premise is very simple. Paul Rudd shows up for his interview on the show and everything goes fine. He and Conan seemed to have chemistry from the very start. When it comes time for Rudd to offer up a clip of his latest project, he cues the clip. Instead of his latest project, the same clip from the ET ripoff/McDonald’s commercial Mac and Me plays every time. This has happened on every appearance Rudd has made on all three of Conan’s shows and it never gets old. He is just so good at making the viewer believe that he is finally going to actually introduce a real clip. Especially as he got involved with huge companies like Disney. He even did it on Conan’s podcast recently. The clip is also really funny out of context.
3. Butterscotch the Clown
This sketch premise was written by Conan writer/performer Andrés du Bouchet. Andrés performs the character of Butterscotch. The premise is based on a real-life news story that came out around the release of IT Chapters 1 and 2 (2017, 2019). Clowns were protesting the movies because they were high-profile blockbusters giving real clowns bad press. In the spirit of fairness and equal representation, Conan offers to let Butterscotch plead his case to the people of the world on behalf of all clowns. Butterscotch has a bouncy demeanor and is very happy to prove that clowns should be loved and not feared. Except, something is off about the clown from the very start. Everything he does is just a bit too strange. His attempts to assuage the fears of children and parents come off as stereotypical signs of a child predator. He lets weird things slip and is generally unnerving. Conan is frustrated and keeps trying to steer Butterscotch in the right direction but ultimately admits each time that Butterscotch is creepy. The humor here for me is the mix of horror and comedy and the surreal props that Butterscotch trots out.
2. Conan The Boss
The premises for these sketches are probably mostly written by Conan O’Brien but seem to largely be improvised. The sketches star Conan himself along with actual members of Conan’s staff. The premises for each sketch probably arose from interactions among the staff. In real life, Conan O’Brien has been the boss on three different shows. He is such a good boss that a lot of people who worked for him followed him from show to show. Many even moved from NYC to Burbank to continue to work for him. In these sketches, Conan usually sets out to do something good for his employees but inadvertently reveals how out of touch he is with his own staff. He comes off as a bully with a heart of gold and an over-inflated sense of importance. A benevolent patron who must deal with his unruly subjects. A lot of the humor comes from Conan’s badgering of his employees until they say something strange and then he pounces on them, ramping up the confusion. The humor for me comes from the absurd dialogue and the knowledge that these are really Conan’s actual staff and not actors.
There are also two notable subsets of this:
Sona Movsesian
Conan’s actual personal assistant since 2009, Sona talks back to Conan like few people can. Her attitude and forthrightness are great to watch.
Jordan Schlansky
A staff member of Conan’s since 1998, he has the innate ability to keep a straight face through just about anything. Encounters with Jordan capitalize on his nerdy obsessions and his cryptic behavior.
1. WikiBear
This sketch premise was written by staff writer/performer Brian Stack. Brian Stack performs the character of WikiBear in all sketches and the sketches ended when he left the show. The premise is that new toys had come out at the 2014 New York Toy Fair. The sketch is actually based on a real toy introduced at that year’s toy fair. WikiBear is a stuffed bear connected to the Internet that can answer questions for kids. In each sketch, Conan turns on WikiBear and tests his abilities. WikiBear is incessantly cheerful and happy to provide accurate facts. Conan asks him about innocuous facts that children might be interested in. After WikiBear rattles off the information, he segues into a much darker subject much to Conan’s shock and horror. The humor for me is the cheerful manner used to discuss dark subjects. Also, WikiBear’s commentary on the flaws of society like “Never Trust a Cop” and “The Wealthy Are Above Morality.”





