10 Worst Celebrity Transformations From Good guy to Heel

“Oh my God, and then Jake came over and he was completely wasted and was being the biggest a@$hole. Uggghh!! I wanted to punch him in the face!”
-Girl on her phone next to me in Lincoln Park, or something similar about a guy being a jerk. every. single. day.

If there’s one think I’ve learned from involuntarily overhearing cell phone conversations of females in their 20’s its that when someone you thought was “sweet”, “nice, “cute, “a nice boy”, or “super cute” is now suddenly acting like an “a@$hole” or, a, “jerk”, it is HUGE NEWS.

So here is some huge news.


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  • My favorite example was Mike Tyson, that is quite the transformation!

  • In reply to Kathy Mathews:

    Thanks for noticing my one "feel good" entrant (even though it was at the end)!

  • Others that could make the list: Dwight Howard, Sammy Sosa, John McCain and Asbestos. On the heels to good guys side, Robert Downey Jr. and Kerrigan. Also love the inclusion of the Punch-Out video.

  • In reply to Joe Grace:

    Oh man, I'll have to consult with you before I publish things from now on! I'm legitimately embarrassed to have forgotten Sammy and strongly agree with Dwight Howard and RDJ.

    Glad you liked the punch-out inclusion. I was surprised how much nostalgia I felt watching such a brief, unimpressive clip.

  • Damn, Sammy...

  • But, wasn't Lance Armstrong always a jerk. An athletic, money-raising-for-cancer jerk. But still...

  • In reply to Kerri Morris:

    Thank you and I completely agree. But I think the masses liked him and I tried to write this from/for their perspective. He is one athlete I knew was juicing the whole time (a European friend in college gave me the inside and correct scoop on him) so it was amusing for me to watch this unravel over a decade later.
    Thanks for reading!

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    Hmmm, 1 out 7 of your "heels" was white (and no, Hulk Hogan isn't white).

  • In reply to Deke Rivers:

    I know, I felt so guilty about it that I made brothers 2 out 3 of my redemption stories. I also included only men, which women did I miss?

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