Celebrity Crush Match: Jon Cryer VS. John Cusack

My two favorite ‘extended brat pack’ crushes face off against one another in a battle of the wits, flix and grand romantic gestures. May the best Jon/John win?

You ready for this, Cusack?

Bring it, Cryer.


Round 1: Chivalry Is Not (Quite) Dead (Yet)

Jon Cryer will serenade you with Otis Redding (via lip-synching and dance).

John Cusack will serenade you with Peter Gabriel (via window-side boom box).


Round 2. Gimme Gimme Moore, Gimme Moore, Gimme Gimme Moore

“No Small Affair”; 1984

Jon Cryer wins Demi Moore’s heart in 1984’s No Small Affair by using his photography skills to start an ad campaign to get people to listen to her sing to help her get a record deal.

Demi Moore and John Cusack Photo

“One Crazy Summer”; 1986

John Cusack wins Demi Moore’s heart in 1986’s One Crazy Summer by using his drawing skills to start an ad campaign to get people to listen to her sing to help raise money to save her grandfather’s house.


Round 3: On the Subject of Self…

John Cusack Says Things Like:

“I have a chronic rebellion disorder. It’s self-diagnosed and it’s been self-treated. If someone tries to corral me to do something I don’t want to do, it gets my Irish up.”

Jon Cryer Says Things Like…

“The fact is, I am a troll.”


Bonus Round 3 and 1/2: When He Gets On Twitter…

Jon Cryer Says Things Like:

John Cusack Says Things Like:


Cryer or Cusack? Cast Your Vote Now:

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