On the left is a photo that purportedly features a young Conan O’Brien doing lord knows what. After it was posted on the HollywoodReporter, he Twittered about it, which people seem to be taking as confirmation that it’s him, although personally I don’t take Twitters written by comedians (much less comedians with extra time on their hands) to be a reliable source for FACTS. But it’s probably him. Doing normal 18-year-old stuff? Meanwhile, on the right there is a photo of American Idol’s Simon Cowell preparing to board a yacht (via JustJared), hopefully so that he can sail out to the middle of the ocean and throw himself in because WHAT IS GOING ON WITH THE HAIR ON HIS BODY? Both of these pictures are such mysteries! Caption them!

Winner will receive special mention in this week’s Monsters’ Ball.

Comments (140)
  1. Being white is hard.

  2. PICTURED: The Evolution of Man

  3. Obviously, Simon Cowell doesn’t use Edge shaving gel.

  4. Young Conan about to look to his left and receive the inspiration for Masturbating Bear.

  5. Mr. Cool Grass Skirt has nothing on Mr. Cool Reflective Sunglasses.

  6. Simon Cowell goes on yet another foreign holiday open thread OR comedians being young and awkward

  7. I have a bad feeling about the dude standing behind Conan.

  8. Simon Cowell really isn’t subtle in his attempts to be cast as the next Punisher.

  9. Dude your hair’s all pitchy dawg
    -Jay Leno

  10. TBS Very Unsettling.

  11. Ode to thee, pale boy
    Still years from your fame and the
    May you dream of success
    In a friendlier television cove
    What dost thou hold?
    A crown of laurels?
    Lest the Big-Chinned one wrest it from thee.

    Ode to thee, dour man
    Acid of tongue and puffy of
    May you dream of addled women and cartoon cats
    And strange large men who say Yo Dawg.
    What dost thou see?
    Reflected in your eyes?
    It is the specter of fame, rapidly fading from thee.

    • Smart host, to slip betimes away
      From stages where glory does not stay,
      And early though the laurel grows
      It withers quicker than your show.

  12. Actually everything about these pictures makes me uncomfortable.

  13. I didn’t know that Young Conan was friends with Young Cary Elwes.
    However, I had already guessed that Simon Cowell would look like just as much of a smug asshole without a shirt as with one.

  14. I asked Charlie about the hair pattern & he said it’s called a sodding strip.

  15. Face Off Two: 2Facer 2Offer

  16. We’ve got to go gayer.

  17. “so then the other hand will pull like this and we’ll call it goatse” -young Conan

    Yuck. Sorry

  18. Three men and a baby.

  19. That’s not how you’re supposed to do a landing strip. :(

  20. Cowell spotted young Conan through a distant window and smiled creepily. The mustachioed man owed him a favor and it was time to collect.

  21. Anybody else see a really creepy face out of Simon’s body hair pattern? *shudder*

  22. “Thanks for making my body look like less of a nightmare next to yours, Simon!” — baby Conan

  23. “Eww”
    - Alan Ball

    [picture on right]

  24. Simon Cowell put Miracle-Gro on his happy trail and it became a happy field


  25. Pictured right: Simon Cowell in good spirits and surprisingly good health after being run over by a car directly down the middle of his torso.

  26. Coming this fall on Mtv, The Lorry Shore.

  27. This picture of Conan was actually taken last week.

  28. Hidden due to low comment rating. Click here to see

  29. “hey, dudes! let’s party!”

  30. You know what’s going here? RIM JOBS.

  31. I’m Team Rococo.

  32. After abruptly leaving Conan O’brien’s Off Broadway production of Taming of the Shrew, Simon Cowell appeared to be in a jovial mood just a day later. When asked why he left Simon said, “You should have seen the costume they wanted me to wear. I simply refuse to look that ridiculous.”

  33. In Conan’s limbo, he’s given the keys to The Tonight Show at age 18 and goes on to host until he’s an old man.

  34. PICTURED: All of your boyfriends.

  35. In Transformers 2, three little boys (left) transform and merge to form Doucheinator (right)

  36. “No one will notice my drooping moobs if I just give my gut a mohawk.” – Simon Cowell

  37. Forever shackled to the ratings of a fickle American public.

  38. The infamous “before and after” ad that led to Glenn losing Dexatrim as a client.

  39. I was hoping to get the inside scoop from you, Gabe.

  40. Some people will do anything to cheer up Keanu:

  41. I think we can all agree Gabe made this week’s caption contest to difficult. I have NO idea where to begin to summarize into a monsterish caption because I am dumbfounded by the awesomeness of both those pictures.

  42. As he stepped back from the long embrace, baby Conan was mortified to realize that in the heat of passion his body glue had come undone and his faux chest hair, used to accent his budding masculinity, was now stuck to Simon’s broader, tanned torso…

  43. Pubescent, bare chested Conan O’brien grasps the wreath, initiating the bizarre body shaving ceremony still practiced on wealthy business tycoon/douches to this very day.

  44. Hidden due to low comment rating. Click here to see

  45. Pictured, left: dream level three.
    Pictured, right: limbo.

  46. You kids with your internet. Back in the 70s, gay porn was an ART FORM.

  47. Hey, Simon Cowell’s lateral chest hair didn’t make it through to Hollywood. :(

  48. Mediterranean Will Forte looks great in that Conan pic!

  49. PIctured on right: HOPA

  50. “I shall cover it with a shiny shirt.” – Simon Cowell

  51. Ups to briadru4 for the inital keanu photoshop

  52. Right: a flat-topped, smug jackass who, when he’s not boring the shit out of me with his glorified karaoke contests, spends his days lactating on the French Riviera.

    Left: An American idol.

  53. this is the weirdest thing that has ever been created that made a lot of people go “wow, wish I’d thought of that.” i love it.

  54. What is this, i can not understand this, what he want to prove,


  55. The guy behind Conan looks like the guy Jake from Almost Twins on Funny or Die.

  56. I can’t even comment because I am stunned into silence by what looks to be a picture of my brother at around age 14. I swear to christ I have pictures of him with the exact same haircut and facial expression as Conan in that picture. There’s still a resemblance now, but back then the two of them could have been twins.

    This is not even supposed to be funny or commented on, I just had to tell someone!

  57. Is that a big happy trail or WHAT?!?!?!

  58. So if that’s Conan at age 18, when’d the rest of the red-headed, six foot seven part of him appear?

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