Holly Madison Photos: Through the Years

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Enjoy these smoking hot Holly Madison photos, from her time in the Playboy Mansion to the present day. What's not to love?

Well, if you're Hugh Hefner, probably a lot.

Holly's making some bombshell claims in her new book Down the Rabbit Hole that makes her life with Hef sound pretty awful.

Whether or not he really tried to buy her or is that miserable in bed, he produced some of these photos, directly or indirectly.

And we're all better off for that.

1. Holly Madison Bikini Photo

Holly Madison Bikini Photo
A bikini photo of Holly Madison ... one that has officially knocked our socks off. As well as our pants. Just kidding. For now.

2. Holly, Hanging Out

Holly, Hanging Out
Holly Madison is not wearing a bra in this picture. That's a shocking development, we know.

3. Holly Madison, Kendra Wilkinson

Holly Madison, Kendra Wilkinson
Holly Madison and Kendra Wilkinson with then-boyfriend Hugh Hefner in 2006. They likely both had relations with him which is kinda nuts.

4. Holly Madison Baby

Holly Madison Baby
Holly Madison poses here with little Rainbow. She's adorable, isn't she?

5. Girls Next Door and Hugh

Girls Next Door and Hugh
Remember these days? Holly, Bridget and Kendra pose with ex-boyfriend Hugh Hefner.

6. Posing

Posing
Holly Madison strikes a pose for the camera. She rarely look this serious, as Holly is a fun-loving gal.

7. Fully Clothed, Caffeinated

Fully Clothed, Caffeinated
Wow. Here is something you don't see very often: Holly Madison wearing a lot of clothing.

8. Picture of Holly

Picture of Holly
Holly Madison finally has a reason to be in the news again! She's come out and bashed Crystal Harris for breaking up with Hugh Hefner.

9. Holly Madison on Halloween

Holly Madison on Halloween
Holly Madison is dressed a farmer for Halloween. We guess. We've never seen a farmer look like this, however.

10. Holly Madison Baby Bump Photo

Holly Madison Baby Bump Photo
Holly Madison is happy about being pregnant. How do we know? Look here!

11. Holly Madison Pregnant Photo

Holly Madison Pregnant Photo
Holly Madison is VERY pregnant. She's also very excited to be a mother.

12. Holly Madison at Miss USA Pageant

Holly Madison at Miss USA Pageant
Holly Madison is engaged! The model made that exciting announcement in June of 2013.

13. Holly Madison and Pasquale Rotella

Holly Madison and Pasquale Rotella
Holly Madison and Pasquale Rotella are married! Congratulations!

14. Holly Madison with Blonde Hair

Holly Madison with Blonde Hair
Holly Madison shows off her blonde hair in this photo. She used to sleep with Hugh Hefner.

15. Holly Madison Book Cover

Holly Madison Book Cover
Holly Madison has a new book out about her life and times in the Playboy mansion. Down the Rabbit Hole. Clever title.

16. Holly Madison of Playboy Fame

Holly Madison of Playboy Fame
Holly Madison of Playboy fame is now writing a book about the good ol' daze in the mansion. Sort of desperate if you ask us.

17. Kendra Wilkinson and Holly Madison

Kendra Wilkinson and Holly Madison
This photo was snapped in 2010. Remember back when Kendra Wilkinson and Holly Madison were friends?

18. Holly Madison and Hugh Hefner Photo

Holly Madison and Hugh Hefner Photo
Holly Madison no longer talks to Hugh Hefner, but she sure is spilling the beans in her new memoir Down the Rabbit Hole.

19. Madison, Holly

Madison, Holly
Holly Madison is seen here at the 2009 Playmate of the Year party. She has posed naked in Playboy many times herself, of course.

20. Holly Madison Style

Holly Madison Style
Holly Madison is, or at least was, Hugh Hefner's #1 girlfriend and all, but she looks kinda ridic with one of her huge fake boobs spilling out of that dress.

21. Mad about Madison

Mad about Madison
We are crazy about Holly Madison, that much is for sure. The girl has it going on ... though we're not quite so sure about that dress.

22. Girls Next Door Pic

Girls Next Door Pic
Just like the good ol' days: The Girls Next Door, Bridget, Kendra and Holly, hung out at Hugh Hefner's 83rd birthday party.

23. Pre-Playboy

Pre-Playboy
Holly Madison was not always a famous Girl Next Door. This is one of the photos that helped launch her career.

24. Holly Madison, Playboy Cover

Holly Madison, Playboy Cover
Holly Madison poses for the February 2009 Playboy cover. We know what you're thinking, guys. We wish she were naked for it, too.

25. Holly Madison Nude Pic

Holly Madison Nude Pic
Two things come to mind when we see this Holly Madison nude pic: 1. We seriously gotta get to this naked car wash ASAP! 2. Why is she wearing shoes? Seems a little unnecessary, doesn't it?

26. Holly Madison Nude Photo

Holly Madison Nude Photo
Holly Madison is going naked for PETA. We think it's a silly ad campaign, one that the organization uses just to get attention. Still, we aren't arguing with seeing Madison in the buff.

27. Holly Madison Naked

Holly Madison Naked
Hugh Hefner's #1 girlfriend stars in their reality show, "The Girls Next Door," and in all of his fantasies. And ours. Well, sometimes anyway. Did we say that out loud?

28. Holly Madison Nude

Holly Madison Nude
The main girlfriend of Playboy's Hugh Hefner

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