10. Fan Corrections (“Conan”)
This is always a solid bit due to the fact that the writers have to get extremely creative and witty to continue to prove that Conan is never wrong. This particular clip only solidifies Conan’s greatness, as it shows he still has connections with “The Simpsons,” a show he wrote for and produced for two years prior to becoming the host of “Late Night.” Is there anything he can’t do?
9. Masturbating Bear (“Late Night with Conan O’Brien”/”The Tonight Show”/”Conan”)
What list of top Conan O’Brien sketches would be complete without a visit from our good friend?
8. Actual Items (“Late Night with Conan O’Brien”)
The hardest part of deciding why this bit makes the top 20 is not whether it is funny enough, but rather, what’s funnier? The fact that the “actual items” are clearly made up or Conan’s inevitable Jay Leno impression to kick things off?
7. “The More You Know” PSAs (“Late Night with Conan O’Brien”/”The Tonight Show”)
Just another way for Conan and Andy to crack jokes about a topical issue. And usually, an opportunity to show you what a creep band leader Max Weinberg is. The more nonsensical the message, the better, as evidenced by this clip.
6. Awful Sports Chanter (“Late Night with Conan O’Brien”)
Who doesn’t love a good chant? Or in this instance, a god-awfully long, rambling chant that seems as though it will never end? While the concept alone is hilarious, it is made infinitely better by the constant “come ons,” as if anyone has a clue how to follow along.
5. Staring Contest (“Late Night with Conan O’Brien”)
“Late Night with Conan O’Brien” turned stare-downs into an art form. Numerous bits employed the gag, and with good reason: it’s damn funny. Along with the original “Staring Contest” sketches, Conan and Max’s “Small-Talk Moments” always ended in awkward stare-downs of their own, and the “Hunky Newcomer” bit added cheesy music to the fold. But it was Conan and Andy who started it all. On his last show before leaving, Andy finally won one, retiring the segment with style. Class, on the other hand, is a totally different story.
4. Photo Gallery (“Late Night with Conan O’Brien”/”The Tonight Show”)
A picture is worth a thousand words. These pictures are worth much filthier words.
3. Conan and Andy on the Aisle/Conan on the Aisle (“Late Night with Conan O’Brien”/”The Tonight Show”)
This bit was hit or miss, but when it hit, it hit hard. The “Spider-Man 2” review at the end of this video is among the best, perhaps rivaled only by a review of “The Score.”
2. The Interrupter (“Late Night with Conan O’Brien”/”The Tonight Show”)
If you can honestly sit through this entire sketch and not laugh out loud at least once, then maybe we were wrong and Conan isn’t for everyone. But it’s doubtful.
1. If They Mated (“Late Night with Conan O’Brien”)
The combination of the offspring photo itself and Conan’s horrified reaction nearly every time is what made this classic bit such a success, and one we wish they would bring back.