Conan O’Brien Has Been Through Hell And Is Living His Greatest Life Now

Sharon Kehoe

Conan O’Brien is one of my favorite people that I’ve never met. I’ve been laughing with this guy for over half my life, and there are some people who – without even knowing them personally – you know are of your kind.

He’s the super smart, incredibly funny guy who never lets an awkward moment go unseen. He’s an improv king who has a vast vocabulary and isn’t afraid to use it. He’s also the most pop culturally savvy over 50-year old who can easily hang with the college kids. He’s an everyman, and although he’s found his fame and fortune, he’s remained a regular guy. I don’t bundle him with the Goslings, Hemsworths, or Biebers. He’s one of us, a normal dude who just so happens to have a television show.

When Jay Leno took down the everyman, sh*t got real. I cried for Conan on that last Tonight Show, because he took one for the team. The uptight older guy pulled the rug out from under our Lego-building, wand-waving, hobbit-loving, pun-wielding, nerdtastic feet. If there was ever anyone who got screwed in the entertainment industry, it was Conan. But he said it himself during his emotional Tonight Show farewell speech, not everyone gets exactly what they want. Watch it below. I’ll wait here, sobbing all over again.

And that’s also what he told the lucky bastards at Dartmouth in 2011 when he gave one of the greatest commencement speeches of all time. (I still hate you, Dartmouth. Just needed to get that out of the way.) Conan took his own shortcomings and told all those graduates that disappointments are inevitable, but not defining.

conan o'brien dartmouth commencement speech

It’s okay to be afraid of failure, but don’t let failure cloud your head devaluing your full potential. Sh*t happens, and for all you know, failure was your greatest moment. Take it from Conan, he has reached new levels of hilarity because he picked himself up and reinvented his comedy.

I’ve never cheered, laughed, and actively supported anyone on TV as much as do Conan O’Brien. Except maybe John Stamos, but I think that’s a given for anyone with a set of ovaries. In celebration of Conan O’Brien, I’ve put together a list of my 10 favorite Conan segments throughout the years, which was extremely hard to nail down, btw. Feel bad for me.

Onward.

Conan, Ice Cube, and Kevin Hart Share a Lyft

conan o'brien ice cube kevin hart lyft

Conan has done two of these now, because the first one was such a massive hit. Conan teaming up with Ride Along stars Ice Cube and Kevin Hart might be the oddest car ride to grace the internet, but goddammit does it work. I hope Cube and Hart keep making Ride Along movies just for these Lyft segments. GIVE ME MORE.

The Masturbating Bear

conan o'brien masturbating bear gif

When I first saw this bear, I didn’t really realize what was going on. What an itch that guy has! All the time! Ah, to be young again. Unfortunately, Conan lost this sketch standard after all the NBC bullsh*t, and now the world is rid of the Masturbating Bear. DAMN YOU, JAY LENO.

Walker, Texas Ranger Lever

conan o'brien walker texas ranger gif

I’ve lost count of how many calories I burned watching Conan pull this lever. Between the insane clips (did anyone realize how awfully amazing Walker, Texas Ranger was?), Conan’s reaction, and the way he played with the audience for more, I could literally watch an entire hour of him just doing this.

If They Mated

conan o'brien if they mated

The most immature recurring sketch Conan has ever done, and it made you laugh from deep in your gut. I remember waiting on the edge of my bedroom carpet, hoping he would have an If They Mated segment on the show. It never failed to pull out the greatest reactions from the audience – and the strangest sounds from me trying to stay quiet in my room, “sleeping,” even though I was silently dying of laughter. Hand over the mouth, not so effective.

Clueless Gamer

conan o'brien clueless gamer gif
conan o'brien clueless gamer lara croft gif

So good, it deserves two gifs. One of Conan’s best segments created for his current show, Clueless Gamer is just plain f***ing genius. I’m not a big gamer, myself, so I feel connected to Coco on this one. His commentary, his lack of knowledge, and his sh*tty playing skills makes this one of his best segments, ever. It’s Conan in his sweet spot, just improvising and making fun of every moment. LOVE.

Triumph the Insult Comic Dog

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BRILLIANT. Everyone should thank Conan for employing Triumph (voiced by Robert Smigel) and giving him a sound stage. If you haven’t watched Triumph at the Star Wars premiere, the VMAs, the Republican National Convention, or in Chicago with Jack McBrayer – just to name a very tiny few – then you haven’t laughed properly yet. GO.

The String Dance

conan o'brien string dance gif

This sorta replaced my favorite “Keep cool, mah babiesss” line Conan would always say after the audience would applaud him in before the monologue (I’m totally showing my age right now), but the String Dance is all that and a bag of FUNYONS. It’s a signature, and a damn good one at that.

That Hair

conan o'brien hair gif

On my bucket list of things to touch.

In The Year 2000…

conan o'brien year 2000

“The future, Conan?” says (insert celebrity name here). This sketch was, literally, before its time – until it was actually the year 2000 and they just kept going with it – and became one of the most beloved. It was just…soooooooo silly. The camera panning work, La Bamba singing SO HIGH, the giggling – gimme it. All day.

Conan Remotes

conan o'brien korea remote

Anytime Conan takes a camera with him and goes somewhere just to mess around, he’s in his zone – the Cone Zone. I would watch a show dedicated purely to Conan going to random places, and this show could last 18 hours. That would be 18 hours well spent. And I’d save them, AND I’d watch them again the next day. Because my life is full and happy. But seriously, this sh*t is always gold, and it only deepens my love for Conan and my goal to meet him someday.

Do you have a favorite Conan O’Brien segment/moment? Share it with us on social at @getfandom!

Sharon Kehoe
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