Skip to main content
  • Facebook
  • X
  • Youtube
  • Instagram
Got A Tip? Email Or Call (888) 847-9869
TMZ
  • News
  • Sports
  • Hip Hop
  • Watch
  • Photos
  • Tours
  • Deals
Got a tip?
  • News
  • Sports
  • Hip Hop
  • Watch
  • Photos
  • Tours
  • Deals

Shows

TMZ
TMZ Live
TMZ Sports

Download The App

App Store
Google Play
  • Contact
  • Careers
  • Privacy Policy (New)
  • Terms of Use
  • Ad Choices
  • Your Privacy Choices
  • Articles
  • Articles XML
  • Updated Articles
  • Updated Articles XML
  • Galleries
  • Photos XML
  • Videos

© 2025 EHM PRODUCTIONS,INC. ALL RIGHTS RESERVED
  • Give Us
    a Call
  • Shoot Us
    an Email
  • Send Us
    a Text

Holly Madison

  • News

  • Videos

  • Photos

missing_image_asset

Holly Hightailing It from the Mansion?

Published: 06/19/2008
Hef's three girlfriends live in a giant mansion with its own zoo, tennis court, grotto and killer party schedule -- so why the heck did Holly tell us she and Kendra are shopping for condos?! Claws Out at the Playboy Mansion
missing_image_asset

Holly Madison: Hef's a Bucket o' Lamesauce

Published: 05/15/2008
Hugh Hefner's #1 gal, Holly Madison, was pissed when TMZ told her he'd never marry her -- but he's making it up to her by getting the Mansion a stripper pole! You mean they don't come standard with every room? Dumb Blonde Down Under
missing_image_asset

Dumb Blonde Down Under

Published: 05/13/2008
Hugh Hefner's #1 gal Holly Madison is learning a new language: Australian! Um ... at least she's trying? Holly Madison Even Makes Tax Evasion Sexy
media_removed

Hef's Playthings: Dressed Like the Girls Next Door

Published: 10/17/2007
No, those aren't Midwest soccer moms on their way to a PTA bake sale, it's two out of three members of Hugh Hefner's harem, Bridget Marquardt and Holly Madison! From Playmates to play dates! The dowdy duo went shopping for Halloween items on Tuesday, dressed in their non-sexiest best mom-jeans and…
... Read More
missing_image_asset

Hef Gets More Bunny for His Money

Published: 07/11/2007
Whoever coined the phrase 'less is more' obviously didn't kick it with Hugh Hefner. Although he usually rolls with just three pieces of arm candy -- Holly, Bridget and Kendra -- Hef added few more peroxide pals to the mix at Ketchup last night. Walking behind his ladies -- no doubt trailing behind…
... Read More
0525_hefner_wireimage-1

Does Hef Have a Bunny in the Oven?

Published: 05/25/2007
He's 81-years old, but is Hugh Hefner ready to change someone else's diapers? After this picture made its way around the web, rumors were swirling that Hef knocked up his 27-year-old girlfriend, Holly Madison, but Hef's reps tell TMZ that the baby talk is all BS.
... Read More
missing_image_asset

81-Year-Old Hef Still Rocks Harder Than You!

Published: 05/14/2007
Octogenarian party dude Hugh Hefner let the Bunnies loose from the Playboy Mansion this weekend -- taking his girls out for a night in Hollywood. TMZ spotted Hef with girlfriends Holly Madison and Bridget Marquardt -- no Kendra in sight -- at Area on Saturday night, and while his ladies were happy…
... Read More
081606-kendra-wilkinson-bridget-marquardt-hugh-hefner-holly-madison

Hef's Big Night Out

Published: 08/16/2006
Hollywood was overrun with sex appeal Tuesday, and TMZ's cameras caught all the sizzling action on tape! Our first stop was Barney's New York in Beverly Hills, where we spotted Heather Locklear looking radiant after a hard day of shopping. Next we rolled over to celebrity favorite Mr. Chow, where…
... Read More
Previous Previous page

ABOUT TMZ

  • About TMZ.com
  • Privacy Policy (New)
  • Terms of Use
  • Ad Choices
  • Your Privacy Choices
  • Articles
  • Articles XML
  • Updated Articles
  • Updated Articles XML
  • Galleries
  • Photos XML
  • Videos

CONTACT TMZ

  • Contact Us
  • Send a Hot Tip
  • Careers
  • Advertising Inquiries
  • Media Inquiries

SUBSCRIBE

Yes! Send me email updates and offers from TMZ and its Affiliates. By subscribing, I agree to the Privacy Policy and Terms of Use

FOLLOW

TMZ APPS

  • Download the TMZ App on the Apple App Store
  • Download the TMZ App on the Google Play Store
© 2025 EHM PRODUCTIONS,INC. ALL RIGHTS RESERVED
Thirty Mile Zone