Crazy And Unemployed Or Not, Charlie Sheen’s Crib Sure Looks Like Winning To Us

- By Bossip Staff Categories: Attention Slores, Ballers, Celebrity Cribs

Charlie Sheen Winning

SMH. This goes against everything those D.A.R.E. agents told us in elementary school.

At this point, it’s pretty obvious that Charlie Sheen’s drug problems have been around about as long as his career. But unlike most celebrity addicts, Sheen waited until his money was straight before becoming the cracked out punchline of the week.

The result: Mr. Tiger Blood/Adonis DNA really is living a much more b*tchin’ life than yours. Flip through and see how Charlie’s living these days.


  • It's Me

    damn he about to loose all that! His shyt will be on the market by the end of this year!

    • Witchcraft

      He aint about to lose nothing, that man is worth close to a billion dollars, the cost of that house is chomp change to a man like Charlie

    • Sally

      NICE NEWS !
      My friend Vanessa, a 25 yrs lady, has announced her wedding with a m’illionaire young man Ronald who is the CEO of a MNC. It’s amazing, she said she just posted her profile on a m’illionaire d’ating s’ite called ———-RichMatchmaker. ℃○M——– – and received his chat invitations a few days later. Then, everything went so well that I can’t believe it’s true! Every love story will unfold on it’s own..——-
      They would also know which Black celebs recently sold this home.

  • purple love

    He won’t loose it he made 2 mill a week this year and he has 8 years of residuals on what like 3 stations

  • RMEs

    Is it really winning if you’re too coked up to enjoy it?

  • whatisthat


  • ok

    Money ain’t everything! If you have to be so drugged and liquored up to endure day to day life that it endangers your life then obviously you are NOT WINNING! I may not have all the expensive diggs,but I can honestly say that I am happy….Winning!

  • don't ask

    Only a drugged out fool would piss away 2 million dollars a week. If he is not bipolar and in need of medication, then he is the poster boy for how drugs can make you lose it all. Now Denise Richards and Brooke Mueller will have to get real jobs because with his lifestyle he won’t be able to live off savings and residuals for long.

  • Do more reading

    How much u wonna bet thats his coke LV tray in the 3rd pict on the bed…LOL, now thats money.

  • lt

    just because it looks, don’t mean it is good.

  • lt

    charlie, get some help.

  • innovatoor09

    Trust me he is not going broke. The man makes money in his sleep. He’s worth about a 100 million right now. He will always have a job, unless he completely has a nervous breakdown, but I think he is acting for the camera’s, because people like looking at a train-wreck.

  • innovatoor09

    He will not go broke, and he will always have a job. Charlie is playing everyone, and acting for the camera’s.

  • Juliemango

    Im sure charlie has good ppl managing his funds he will keep his head above water!!!

  • Daisy Jay

    As much as I think Charlie is purely deranged, unfortunately he IS winning. He may be a junkie, but he’s got too many people on his team and they do everything in their power to make this guy stay on top.

    Bi-WINNING! Winning here, winning there! Uhhh DUH!

    • Old Spice

      Yep, Michael Jackson, Elvis Pressly, Anna Nicole Smith, etc… were “winning” like this too. All the money in the world can’t keep you from killing yourself with a reckless lifestyle and drug addiction.

  • a.m.

    i swear charlie sheen is the new chuck norris
    for some definate #winning check out my blog at

  • Daisy Jay


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