#2 HOLLY MADISON
WHEN HEF DATED: 2001-2008
• America thought she'd be the one, but apparently she wanted marriage and kids with him more than he did. We'd call any other guy insane, but what can you expect from Hef? Still, for some reason, we actually felt this break up. Damn.
CLICK HERE TO SEE #1 ON HEF'S HOTTEST GIRLFRIEND COUNTDOWN
oink January 14th, 2010 at 03:59 PM
Hefner is the most luckiest man in the world ...plus his round bed sleeping or playing at night time activities... Support our U.S. Troops~~~!!! Go Team~~!!
kevin January 15th, 2010 at 12:52 AM
you forgot the Bentley Twins, Tina Jordan to name a couple, the other twins and bridget have no business on this list
Alex January 15th, 2010 at 01:36 AM
This list might be the biggest crock of crap I have ever seen. To put the Shannon Twins on the list is a joke and to put them above Barbi Benton is even more pathetic. This list is laughable and nothing more
Cpm January 15th, 2010 at 02:02 AM
Hef's girlfriends back in the 60's and 70's were much hotter than the plastic bimbos portrayed as his 'girlfriends' since his divorce. This list is woefully inadequate. Anything he's had in the last 20 years is pure PR to maintain his image. Today it's just creepy.
Lulu January 26th, 2010 at 09:19 AM
are you kidding me? crystal? shes just some slapper you see at a bbq jumping on the fame train to the bank in we-never-had-sexville. even iv been with a girl far hotter than the twins. this is crap. hef himself would call this crap
Kayleigh March 24th, 2010 at 06:22 PM
Where's Tiffany Holliday in this? and Stephanie Heinrich? Thw twins are horrid and have no right being on there, you seem to be focusing on the girls next door the most because they are more publicized aswell as Barbi Benton and Kimberly Conrad [even though she is gorgeous]
Nicky July 14th, 2011 at 08:25 AM
What about Dasha..She was beautiful ...
dalilah morel April 9th, 2012 at 11:48 PM
quisiera ser una chica pleyboy... saber que hay que hacer para ser una y si aceptan morenas???
dalilah April 9th, 2012 at 11:51 PM
en realidad me gustaria ...espero una respuesta ,aunque sea un no...jijij