Frank Sinatra's "pull my hairpiece" challenge

"I will allow you to pull my 'hairpiece;' if it moves, I will give you another $100,000; if it does not, I punch you in the mouth. How about it?" -- Frank Sinatra

Frank Sinatra's "pull my hairpiece" challenge


  1. I had a math teacher who offered a similar deal. It’s probably just as well no one ever took her up on it. She wouldn’t punch a student in the mouth, but she probably would have flunked anyone who pulled her hair even if it came completely off and left her looking even more like a California condor than she already did.

    1.  This has always been my favorite moment from Antiques Roadshow. The woman is just so goddamn adorable.

  2. “Regarding my “tough reputation” you and no one else can prove that allegation.”

    Except possibly by publishing my offer to punch you in the mouth.

    And I love the old school CC license.

  3. It’s too bad that Sinatra comes across as such an ass in the letter otherwise (especially the misogynist stuff).  The hairpiece challenge is gold.  Of course it would almost be worth it just say you were punched in the mouth by Sinatra.

  4. I think Sinatra the man is best left in the shadows.  As a crooner/entertainer, he’s incomparable, but as a man, he has the sad quality of a simpleton and a bully.  The one thing he couldn’t completely control in his life (besides the women) was the press.

  5.  His music is shallow and repetitive. Fantasy crap for suburban dads.

    Basically his music and stage persona says “I’m cool, cooler than you. You wish you were me” zzzzzzzzz

    1. opinions…

      there is the small matter of being able to sing extraordinarily well, though I don’t imagine your convictions can be swayed.

      1. there is the small matter of being able to sing extraordinarily well…..

        …..for the first 20 years of a 50-year career. He should have smoked a lot less or retired a lot earlier.

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