Feb 19 2009 10:48 PM ET

Conan O'Brien: Five memorable moments from 'Late Night'

Categories: Television

When Conan O’Brien leaves for Los Angeles after this Friday’s show, he’ll be ending a 16-year-run on Late Night that produced some of the funniest moments in recent TV history. To mark the occasion, we put together a list of five of Conan’s greatest hits. Check them out, and be sure to give us your picks!

5. December 1998. An impromptu game of “Suck and Blow” results in a quick kiss betweenConan and supermodel Rebecca Romijn. Realizing what he’s just done,Conan gives a triumphant fist-pump, throws his chair into the air,and then falls to the floor. Wouldn’t you?

4. January 2008. With the writers strike in full swing, a bearded O’Brien dons a glittery jacket and a cowboy hat for a full-band rendition of “Blue Moon” — all to prove that he can still put on a show without his usual staff of jokesters. As if we ever doubted him.

3. April 2002. Conan’s visit to Martha Stewart’s Westport, Conn., compound (whichhe described as “something a Bond villain would have inside avolcano”) gives a chance for the comedian to run havoc in Martha’sperfectly organized studio. Who else could get the domestic diva to eatcheese whiz off her own hand?

2. March 2006. After joking about his uncanny resemblance to Finnishpresident Tarja Halonen, O’Brien finally travels to the Scandinaviancountry to come face to face with his doppelganger. The resulting show is one of the greatest — and weirdest — moments in the history of late-night TV.

1. October 2000. An apple-picking trip in upstate New York with Mr. T provides a solidfive minutes of mind-bending hilarity. One highlight: Conan points outan apple with a bee in it, and Mr. T immediately swings into action,smashing it with his elbow and growling, “T one, bee zero.” We pity thebee that messes with Mr. T.

Your turn, PopWatchers: What are your favorite Conan moments?

Comments (1-30) of 194 Add your comment

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  • dazzlefresh

    Any of the amazing Walker Texas Ranger Lever segments. Always cracked me up.

  • Rahul

    I loved when Triumph harassed the geeks on line waiting for Star Wars. Also when Conan switched clothes with a much shorter guest during a show; can’t remember who exactly that was though.

  • mv

    A long time ago.. It was one of his very first shows.. Conan and Andy decide to drive around New York to see if anyone of watching his show.. So Funny!

  • Secondrink

    I loved Conan with Ted Nugent. It’s a blend of Conan playing guitar in Memphis and indiscriminantly shooting things with Hunter S Thompson. What’s not to like?

  • galtwish

    Conan O’Brien on a firing range with Hunster S. Thompson in upstate New York. They drink Chivas and shoot the NBC corporate logo. It ends with Conan towering over a FAO Schwartz bear that is burning from being hit by a flare.

  • ct

    I loved the night that Conan had an audience made up entirely of kids. I remember Dave Foley was a guest and he looked either surprised or slightly annoyed at the constant low chatter coming from the audience that wasn’t paying any attention. pure genius.

  • Dave

    I remember when he put in the zip line and started every show by sliding down the line. Every show, he would keep trying to one up his zip line entrance.

  • Kathie

    Andy Richter goes to a KISS convention. I had refused to watch Conan until I saw this remote. Haven’t missed an episode since.

  • Chaddogg

    Conan goes to Ireland to his ancestral home….I saw it in a bar, and couldn’t hear it, but the whole thing was RIDICULOUSLY funny to watch. Wind was blowing in gale-force gusts….him discussing famous Irish people in America like Shaquille “O’Neal”….amazing.

  • Meier

    Rahul, I think that was Roberto Benigni.

  • Stewart

    The funniest of all time was the show when he showed clips that could not previously be aired, and he showed the clip of Walker, Texas Ranger where Walker told a young Haley Joel Osment that he had AIDS. That still to this day is the funniest thing I have ever seen. EVER
    Clip below
    <embed src="http://www.videovat.com/videoPlayer.swf" quality="high" wmode="transparent" flashvars="videoId=967" width="424" height="373" name="videovatPlayer" align="middle" allowScriptAccess="always" allowFul

  • Anonymous

    A haunting song dances in my mind: “In the Year 2000…In the Year 2000″ (Higher pitched on the repeated verse!)

  • Tom

    if i had to choose one, it would be when he went to a recreation of an old-timey baseball game and played in it

  • Anonymous

    Triumph the Insult Comic Dog heckling the Star Wars fans…makes me laugh just thinking about it.

  • H

    Stewart!!! That Walker clip is definitely my favorite one. The music right before Haley speaks and the face his makes were just so funny. I remember watching it with my roommate, and we laughed until we cried HARD. I recorded the replay on tv the next day with my handheld camera and still watch it sometimes.

  • Sharon

    The clip which shows Conan being coached to be a department store Santa Claus is hilarious! It was from about 8 or so years ago.

  • Anonymous

    Triumph at the Star Wars convention….Another really fun one was when Conan went to Truck Driving School.

  • maryb

    This is an oldie, but when they do the “we are the world” like benefit song and Sting shows up. Genius.

  • Cristin

    My favorite sketch was when Ben Stiller was a guest, probably back in 1996 or 1997, and he started performing songs from Jesus Christ Superstar with Janeane Garafolo as Mary Magdalene and Andy Richter as an apostle.

  • julie

    My favorite Conan moment? It didn’t air, but here it is: The first time I saw the show taped live, and Conan came out for his preshow warm-up, he got in my face and did his trademark tiger growl, then pretended to spar with my husband over me. I was a puddle on the floor at that point, and needed to be mopped up. *happy sigh*

  • May

    I like these 2 the best: one where he’s starting a boy band (Backstreet Boys or N’sync like band) & one where he’s comparing his Ford Taurus with Ferrari or Porsche.

  • steve in SD

    5 Andys singing Boyz II Men. Classic! Don’t forget the weeklong 10th anniversary celebration of Dirty Dancing! Conan would randomly insert a clip of “Nobody puts baby in a corner” in the show. Hilarious

  • FabK

    Quackers the S*** eating Duck! Not so much Quackers, but Conan’s reaction. Loved it!

  • jasmine

    One word: Pimpbot

  • ayale99

    The Walker Texas Ranger lever! Conan would pull the lever to show another ridiculous Chuck Norris action scene. Classic.

  • G

    Conan at trucking driving school is still my favorite. Conan Playing Old Timey Baseball is a close second!

  • Sharlin

    I loved it when Triumph was at the Star Wars premiere. Another was when conan went to some Texas city where his show was like at 3 AM and trying to see who knew about him and stuff. I think it was at an airport. It was hilarious, lol.

  • JCJ28

    The trip to Ireland and his ancestral castle was amazing.

  • Samantha

    Its time for Conan to move on.He wants to do other projects.

  • Ken B

    Conan visits Old Time Base Ball at Old Bethpage Village Restoration on Long Island. He absorbs the period jargon and dons a uniform and the fun runs a full 8 minutes.

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