Holly Madison: Through The Ages

As we’ve been telling you for the past few months, there’s trouble in the house of Playboy. According to sources, Hugh Hefner and his lead lady Holly Madison have finally split after having been on the rocks for a little while now, and its all do to the arrival of a set of twins who’ve just moved into the house.

Since Holly moved into the mansion seven years ago, she’s undergone quite the transformation. Check out our photo gallery of Holly to see how she’s changed, both physically and otherwise, throughout her relationship with Hef. [Getty Images]

Picture 4 of 13
Picture 4 of 13

Seen here in September 2003, after two years of living in the Playboy Mansion, Holly's spoken openly about the plastic surgery she's undergone.

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26 Responses to “Holly Madison: Through The Ages”

  • Nicey says:

    This can not be holly!

  • me says:

    DAMN!!!!!!!!!She was a hot mess before Hef. She should just thank him for making her pretty and move on! thats kinda irresponsible to want children from someone who doesnt have that kind of time on his plate. The poor child will grow up without a father and that is selfish of her to demand!

  • RYAN says:

    SHE IS NOT PRETTY NOW SHE IS UGLY %&_*)))(@!&~($( %)#!!))_`%$(^_~)_ WHO WILL B BROKE SOON,YUCK!

  • Shellie says:

    WOW.. i think she looks like an awesomewild child.. Until she got all serious n jelous over the other GAZILLION women in Heffs life!

  • Sweetrainbow1 says:

    HOLLY MADISON IS A GOLD DIGGING $+$$#&^~#^#^*~)+`

  • mimi says:

    Hey, I am so glad for her. She did what she did because she wanted. She must of cared for hef somewhat… Also, he knew what he was doing when he got involved with a much younger women. So Girl friend more power to you and best of luck…

  • bridget says:

    ?????????

  • mily says:

    she diserv the best i se that she realy love the man , just wante kids nothing wroung with that she is beatuful and will find a man that realy love her . that old man will mis her one day . i saw the show and think that al 3 gril realy care about him. he sould be carefull now with the women tha he meat. holly be happy you are beautifull… from a frind from puerto rico emily

  • my name is amera and will like to be yourfriend my 3474722153 says:

    Comment is require i like see you in person , i cant waite

  • O_Jess_01 says:

    DAMN!!! I see Girls Next Door every sunday and she does not look like this at ALL!!! I am sorry hef, but bridget is more beutiful than holly and Kendra is BAD ~*@%$!+`_`_^++( Besides on every show that i see it looks like holly dont even want to be near hef!!! i say hef gets a new girl cause holly is a GOLD DIGGER!!!!!!!!!!!!!!!!!!!!!!

  • Niki says:

    Holly is a beauitful person inside and out and unfortionately wanted things from a man who didnt want to go down that road again! I think Holly has a lot of love from friends, family and her fans and she will succeed in any thing she does!!!!

  • Claudia says:

    I think Hugh Hefner is a fool. Holly really seemed to love him. He always told her he loved her. Why couldn’t he marry her. This man does not know what love is. I had a husband like that, always cheating but “he loved me” or so he said. I got rid of him too. Cheer up Holly you will meet the right man not a horndog. I thought Hefner seemed like a nice man, now I know better, I guess he like a lot of other people use others by playing on their emotions. Shame on you Hugh Hefner.

  • Lisa Ortega says:

    How SAD!!!! I had no idea they were broke up till now! She’s a new Director too for Playboy, so atleast she got that out of it. They really seemed to love eachother, but having children is a huge thing and you have to be ready for it, and Hugh wasn’t ready to do that again at 80 something, and I don’t blame him. Poor Holly!!! She’ll be fine. She’ll find someone else, this time maybe someone younger with more vigger and vim. :)

  • Cassidy says:

    This man is stupud he had has soo many women I thought he and holly would made a cute family but this man lives on and off women it seems like he is using these women. Hef should be getting married he might have not long to live so he should spend his time finding love with Holly and make a family with her they will make a beautiful together

  • ldinokc says:

    leave her alone…geez she needed it

  • That Damn Chick says:

    Ithink it’s time for him to sit down. After while Viagra, side effects will kick in. So, forget how young he feels the body gets tired and he found someone that actually loved his wringled %+%_~*(_`^($#+@ He better think about it… And give her two damn kids while he still can….. Sorry Holly, I uess it wasn’t meant to be. You shouldn’t have to share a man anyway….

  • Veronica says:

    Holly is lucky that she is still young. Hopefully she was smart enough to pay herself and save that money … She should enjoy being single and not worry about men. That is when the right one will present himself.

  • Shannon says:

    OMG, that’s Holly?????? She looks GROSS!! Not even Playboy Bunny material!! She looks like a 50 year old, bony, mountain toothed geezer in this bunny photo!!! How did she improve so much?????????? Because she’s beautiful now.

    It’s crystal CLEAR what’s going on in Hef land. Holly is is “wife”, Bridget is his homely sister and Kendra is his “daughter”. He is living out a sick fantasy of incest. He gets to bone his wife, his sister and his daughter. Gross.

    I don’t get the whole future of no wife and kids thing though. She’s not been his wife for years, so what’s new? And as far as a future as a dad?? Um…Holly, sweetie, Hef is 82, he’s going to DIE when your child is a toddler. You’ll be a SINGLE mom regardless with Hef. Do you think he’s going to live forever?? Do the math sweetie.

  • Shannon says:

    Claudia dear, they’re ALL fools. Who agrees to be one of three girlfriends? And what beautiful 28 year old holes up with some 82 year old and wants him to be the father of her children ? They made their choices. Don’t feel sorry for them. They ARE fools. They all need serious therapy.

  • Missy says:

    I think that she looks like an old librarian. it has ALWAYS blown my mind that she was a bunny. she just doesn’t look the type. give a librarian fake boobs and she is still a librarian

  • Joe says:

    Id stil _+$@@!)(%_~$##+^ the &#%*`@$$!+~%%@!$ out of her sooo yeah…

  • alexandra says:

    Damn she was pretty ugly before playboy

  • Vanessa says:

    Wow. MUCH better!

  • I think Holly is a real smart girl and I think she did the right thing by leaving and finding some one else. Shes a real beautful girl and I admire her in every thing she does I watch all the Girls next door epoisodes and I think all you guys are awsome.

  • JESS says:

    wow she looks pretty old in the 1st pic than she does now. SHES WAAAY PRETTIER NOW :)

  • Tiffany says:

    SHE WAS UGLY AND NOW SHE’S PRETTY THANKS TO PLASTIC SURGERY. SHE’S NOT A NATURAL BEAUTY. END OF STORY.