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Holly Madison

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Was working as a "Hawaiian Tropic" model when one of Hugh M. Hefner's friends saw her and put her on the Mansion's party list. The Midsummer Night's Dream party was her first Mansion experience. She saw lots of celebrities and centerfolds and was most excited to meet Hef, Seth Green from the…

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Also Known As: Holly Cullen, Holly Madison

STORIES

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Holly Madison -- As American As Apple Pie Holly Madison -- As American As Apple Pie
Holly Madison & Wayne Newton:… Holly Madison & Wayne Newton: Statuesque Duo
Holly Madison -- Worm Dangler Holly Madison -- Worm Dangler
Holly Madison Busted in Underage Scheme Holly Madison Busted in Underage Scheme
Holly to Hef -- Get Off My Back! Holly to Hef -- Get Off My Back!
Girls Next Door Get Wet in Vegas Girls Next Door Get Wet in Vegas
Hef's Ex Sets Record -- 300 Chicks at Once Hef's Ex Sets Record -- 300 Chicks at Once
Holly Quits on Playboy for Trick Turner Holly Quits on Playboy for Trick Turner
Hugh Hefner Hates Criss Angel Too Hugh Hefner Hates Criss Angel Too
Ho-phie's Choice -- Playmate's Incision… Ho-phie's Choice -- Playmate's Incision Decision
Criss & Holly: Lifestyles of the Rich… Criss & Holly: Lifestyles of the Rich and Classless
Holly & Criss -- Love at First Bite Holly & Criss -- Love at First Bite
Hef Ain't Nothing But a Horn Dog Hef Ain't Nothing But a Horn Dog
Holly Goes from Hef's #1 to #1 Bitch Holly Goes from Hef's #1 to #1 Bitch
Holly Still Plays House with Hef Holly Still Plays House with Hef
Single Holly -- Sketchiest Person Ever Single Holly -- Sketchiest Person Ever
Holly Madison: No Thong in a Bunch Holly Madison: No Thong in a Bunch
Holly Would, Hef Won't Holly Would, Hef Won't
Holly Hightailing It from the Mansion? Holly Hightailing It from the Mansion?
Holly Madison: Hef's a Bucket o' Lamesauce Holly Madison: Hef's a Bucket o' Lamesauce
Dumb Blonde Down Under Dumb Blonde Down Under
Hef's Playthings: Dressed Like the Girls… Hef's Playthings: Dressed Like the Girls Next Door
Hef Gets More Bunny for His Money Hef Gets More Bunny for His Money
Does Hef Have a Bunny in the Oven? Does Hef Have a Bunny in the Oven?
81-Year-Old Hef Still Rocks Harder Than You! 81-Year-Old Hef Still Rocks Harder Than You!
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PHOTOS

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Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
Holly Madison at Wet Republic
<b>Holly Madison</b> at Wet Republic
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VIDEOS

1-5 6-10 11-15 16-20
Holly wouldn't say if she's seen… <b>Holly</b> wouldn't say if she's seen his "magic wand" yet but it <b>...</b>
There are a lot of stupid World Records out… There are a lot of stupid World Records out there -- most <b>...</b>
Usually when couples that live together… Usually when couples that live together break up, one person <b>...</b>
Holly Madison says there's no bad Bunny… <b>Holly Madison</b> says there's no bad Bunny blood between her <b>...</b>
Holly Madison must be vigorous on the pole… <b>Holly Madison</b> must be vigorous on the pole -- check out those <b>...</b>
Hugh Hefner's #1 gal, Holly Madison,… Hugh Hefner's #1 gal, <b>Holly Madison</b>, was pissed when TMZ <b>...</b>
It might seem obvious -- but when Holly… It might seem obvious -- but when <b>Holly Madison</b> was asked <b>...</b>
Holly Madison ordered up some sloppy… <b>Holly Madison</b> ordered up some sloppy seconds in Las Vegas <b>...</b>
Holly Madison dropped some big news on us… <b>Holly Madison</b> dropped some big news on us tonight -- her <b>...</b>
Now that she's no longer schtupping the… Now that she's no longer schtupping the boss, <b>Holly Madison's</b> <b>...</b>
Holly Madison's done with bedding an… <b>Holly Madison's</b> done with bedding an old fart -- and moved <b>...</b>
Hef's three girlfriends live in a giant… Hef's three girlfriends live in a giant mansion with it's own zoo <b>...</b>
You won't see Hugh Hefner around if his… You won't see Hugh Hefner around if his ex <b>Holly</b> marries that <b>...</b>
No better place to bring up the nasty… No better place to bring up the nasty subject of 82-year-old <b>...</b>
Leave it to Hugh Hefner's main girl to… Leave it to Hugh Hefner's main girl to confuse the words "tax <b>...</b>
Hugh Hefner showed up to Ketchup last night… Hugh Hefner showed up to Ketchup last night with five <b>...</b>
As seen on TMZ TV -- May 15, 2009 As seen on TMZ TV -- May 15, 2009
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