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Funniest Conan O'Brien Moments

Tuesday, Aug 10, 2021, 9:23 am

1.Punched by a monkey

You have to admit that seeing anybody being punched by a monkey is funny and the fact it happened live on TV just made it so much better. The best thing is that we can go to YouTube in order to watch it and if you are not too keen on Conan, then you will probably be rooting for the monkey.

2.William Shatner

This was such a funny moment as he invited William Shatner onto his show in order to recite the lyrics from Umbrella by Rihanna. There is just something so, so strange about the entire thing, but then that is what made it so funny.

3.The Tonight Show

He moved to the Tonight Show in 2009 and did a sketch that appeared to show that he forgot it was now on the other side of the country. The sketch involved him running across the country in desperation to get there.

4.The across show brawl

When the writers went on strike in 2008 he decided to do a comedy sketch with Stephen Colbert and Jon Stewart. Basically it resulted in them having a bit of a brawl, which was so funny to watch.

5.Looking like the Finnish President

In 2006 it was discovered that he did actually look like the President of Finland. The problem here is that the President is female, but he still traveled and even did a show.

6.Old style baseball

This is a segment that even Conan thinks is one of his best as he had a shot at old style baseball. It is certainly one that you need to check out as it is one of the best sketches of this style ever.

7.Roberto Benigni

In this segment both Roberto and Conan were thinking about the phrase linked to walking in another person's shoes. However, they decided to take it further and exchanged pants on live TV and when you consider the difference in their size it was harder than you think.


8.Jennifer Garner

Jennifer Garner made the mistake of trying to tell Conan that snuck was not a word. Of course he then pulled out a dictionary and proved it to her before teaching her all about the word.

9.Mr T

In the year 2000 he decided to go apple picking with Mr T. The segment is an absolute classic and it is certainly one of the best that he has ever done.


10.His birthday presents

Perhaps the funniest birthday present he was given came from Will Ferrell. Basically Will decided to give him something Irish, so he rocked up as a sexy leprechaun and it certainly made an impression on everybody.

11.The insult comic dog

This has to be one of the best things that he ever came up with because everybody loves the insulting comic dog. He appeared on the show in 1997 and since then he has certainly managed to become a stalwart.


12.The noose

Conan is known for his humor and when he took over from David Letterman he gave a glimpse of what was to come. The joke was that he was fed up of the apparent pressure on him, so he put a noose around his neck in his office. It was harsh, but also very funny.


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