Since Conan first started hosting Late Night back in the 90’s, it felt like a different kind of show, almost like a club you were a part of. It wasn’t the typical late night show that consisted of your everyday sketch comedy, desk pieces and forced interviews. Yes, there were nights that Conan came across as business as usual- more often Conan went to bizarre places, that your parents who grew up on Leno and Letterman, didn’t understand. The best shows, however, aren’t the travel shows, or the ‘live at some crazy event’ shows. They’re the episodes with Conan regulars…the guests who are friends with Conan who you always knew you could rely on for a ridiculous and goofy segment. These are the guests that forced you to stay tuned past “The Masturbating Bear”, “In The year 2000” or whatever other bit you loved most because you knew it would be a few minutes of stupid fun.

Norm Macdonald

Any fan of Conan will immediately think of Norm Macdonald at the top of a favorite guest list, because of his bizarre appearances on Conan’s various shows over the years. When Norm is on the couch he uses his bizarre brand of anti-comedy that works even if you’re not usually a fan of the style. You could have a full debate with other Conan fans about Norm’s best appearance. Is it the time he told a moth joke that took about 5 minutes to get to the punchline? OR maybe the time he completely took over Conan’s interview with snowboarder Gretchen Bleiler or when Courtney Thorne-Smith was on and he just threw in digs at her career choices and Carrot Top, too. Norm is basically Conan’s shitty interview savior. When you see Norm is on the show you know it’s going to go off the rails and end up being a segment you don’t want to miss.

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John Krasinski

Obviously people are more comfortable around their friends. While John Krasinski definitely has some memorable bits on other late night talk shows, his appearances on Conan have a different feel. The reason it’s different is because before he was pranking Rainn Wilson on The Office, Krasinski worked for Conan so when he shows up to be on the show it isn’t just your run of the mill interview. Instead you’re watching two friends catching up and doing goofy shit. Conan once said that when they were off air, Krasinski showed him a hilarious impression of a marionette puppet so now whenever John is on the show Conan makes him do the impression with different themes. The two best puppet bits include an incredibly detailed basketball referee impression, and a fisherman. Hopefully this will lead to a string themed dance off since Conan is known for that as well.

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David Bowie

David Bowie is undoubtedly one of the coolest people to ever walk the Earth, which is what made his appearances with the lanky awkward nerd that is Conan O’Brien so funny. It is hard to choose just one of his best moments on the show. Their duet is hilarious, not only because of Conan’s ridiculously self-indulging lyrics, but because Bowie is able to throw in quick one liners with great timing that show you his great comedic side that not everyone is aware of. Another great moment had Conan poking fun at all of the different styles that Bowie has gone through over the years. It is always cool to see someone who was a legend and a serious artist have a lighter side. Getting to see the funny side of someone as mysterious as Bowie was a treat fans would look forward to any time Bowie would grace Conan’s couch.

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Paul Rudd

Every time Paul Rudd is on Conan you know exactly what is going to happen. Paul Rudd is going to promote a clip from his movie, and he is going to promise it isn’t a clip from the movie Mac & Me and then guess what…. he shows the clip from Mac & Me. And sometimes Rudd even says “Okay, here is the real clip” and just shows it again. You would think it would get annoying and old after about 15 years, but it is just as funny every single time.

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Harland Williams

Even for those of you who aren’t fans of Harland Williams’ movies or stand up you have to love his Conan appearances. When Harland is on the show, there’s a vibe similar to the Norm Macdonald style of interview– Harland just spends his time on the couch fucking around. Williams isn’t interested in acting professionally on the couches of late night shows and Conan’s couch is one where you are more than welcome to let loose and have a good time. Back during Conan’s Late Night time on NBC, Harland asked Conan if he ever pretended he was Jiminy Cricket and sang When You Wish Upon A Star…and then proceeded to sing it to the audience. Good dumb fun.

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Jack McBrayer

Another former staff member, Jack McBrayer appeared in over 80 sketches when he worked for Conan between 2002-2004. Even though those sketches were great, it’s always entertaining when McBrayer comes back either as a couch guest or randomly popping in during a segment during the first half of the show. When McBrayer is on the couch, they usually talk about how cheap Jack can be or just stupid silly stuff like McBrayer doing an on-the-spot Bud Light ad. McBrayer’s best appearance has to be when he went to The Weiners Circle– a famous Chicago Hot Dog stand that is famous for berating costumers in Lincoln Park- and ended up bringing Triumph the Insult Comic Dog in for backup. That segment gets watched endlessly, and their chemistry even earned them a show on Adult Swim.

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Abe Vigoda

Abe Vigoda was one of the first guys to become one of Conan’s bizarre regular guests. Some could argue that in the early days, Vigoda was just as important to the show as Andy Richter or LaBamba. To be fair, Abe wasn’t a couch guest, but every time he popped up on the show it was a best of all time moment, and those segments remain the best even after Conan’s 20+ years on different networks and in different time slots. There are too many to list all of them, but some of the greatest segments are when Conan showed a “Vigoda Tree” around Christmas time, the “Vigodal Eclipse”, or even just quick pop ins like “Vigoda with Lime.” Once Conan went to the Stage Deli and Abe just popped in at the end of the piece. His last appearance was both emotional and funny– when Conan and his team moved to LA for The Tonight Show, it was the end of the reign of Abe. No longer could they get a random idea and have Abe pop in three hours later. So when they went to LA, it was time for Conan to set him free. When Abe passed away it was a sad day for all Conan fans who had been wanting one last appearance for a long time.

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Stephen Colbert & Jon Stewart

After Colbert claimed he made Mike Huckabee, Conan claimed he made Colbert therefore he made Huckabee and the battle for “Who made Huckabee?” began. This feud turned into a hilarious rivalry that would span multiple weeks and crossover through all three of the shows. Things really heated up when Colbert got his buddy Jon Stewart in on the action, which all led to a hilarious brawl backstage on the set of Late Night. When Conan went to the 11 o’clock hour, things only got funnier with the duo showing up when Conan returned to New York City when he brought his show on the road. This was just a fun feud that you had never seen before because up until then, the only two real guys in the game were Leno and Letterman and those two weren’t gonna make up any time soon. Getting to see three people all from similar comedic backgrounds just having a good time because they love what they do, was a treat for every late night comedy fan.

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