Frank Sinatra's "pull my hairpiece" challenge


20 Responses to “Frank Sinatra's "pull my hairpiece" challenge”

  1. Christopher says:

    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.

  2. don’t break the copyright , gotta put page 1 up here too.

    nevermind, still learning the internets.

  3. oasisob1 says:

    “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.

  4. l337n00b says:

    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.

  5. Nash Rambler says:

    Hairman of the Board.

  6. Pete Anderson says:

    Here’s Mike Royko’s awesome response, “Mr. Sinatra Sends a Letter”:

  7. Somehow I don’t ever see the Trumpster offering a similar challenge.

    Although in fairness, I suspect he wears an elaborate comb-over rather than a rug.

  8. franko says:

    seriously. sinatra was a badass.

  9. Petzl says:

    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.

  10. pjcamp says:

    What do I get if it makes you fart?

  11. noah django says:


  12. someguyyouvenevermet says:

     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

    • noah django says:


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

      • Antinous / Moderator says:

        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.

  13. Sinatra was the Daddy of the mack daddies. Baddest mofo around.

Leave a Reply