Brande was one of Hef's girlfriends before he "settled" for his current 3some of girls. Brande is also the only Baywatch regular to earn PMOY honors. She's currently married to a former NFL lineman, keeping the tradition of football player hot-chick alive and well. Of particular note, while doing this painstaking research, she has the funkiest nipples of anyone on this list.

Dalene's claim to fame is being the first PMOY to appear with not a whisp of pubic hair. Way to go Dalene! History will look down upon you favorably as a trailblazer in this world! She was also the first to feature a lower back tattoo, inspiring countless targets for men everywhere.

Jodi Ann was the first PMOY to have a college education, proving either that smart girls are too smart to be in Playboy, or that dumb girls are dumb enough to take all their clothes off for men. Either one, we're perfectly comfortable with it. We're also pretty sure there were no girls that looked like that at our college, or we'd probably have been kicked out there even earlier than we already were. Jodi is currently married to race car driver Michael Andretti.

Tiffany turned her success as PMOY into a lucrative career as trophy wife to Rascal Flatts singer Joe Don Rooney. Needless to say, she now has millions of dollars to spend, and great breasts in need of accessories. She was also a contestant on Celebrity Apprentice, being the first one kicked off. We're guessing the Donald only likes his hot women working underneath him, not with him (see the clever pun there? that's why you visit sites like this!).

Jayde is perhaps most famous for her trademark, a tattoo of "RESPECT" inches above her "secret spot" (which ironically, isn't very secret any more). We hope her definition of respect entails standing at full attention as you look at her naked, because the other things we're doing at the same time sure aren't very respectful at all.

Heather is a part of NFL Draft lore, by dating several of the top QB's taken in the 1999 draft. Unfortunately for her, that draft featured several of the biggest busts in the history of the draft. Heather dated Cade McNown early on, then switched to Tim Couch who she's currently married to. Almost as bad a decision as the Browns on that one. Rumors abound that McNown traded Couch a Porsche for Kozar. I hope for McNown's sake that the Porchse had 36D's and could f* like a rabbit, or he got a bad deal on that one.

Carmella married NFL QB Jeff Garcia in 2007 which served 2 purposes - it laid to rest all the rumors of Garcia being gay, and it locked up for Carmella the "Hottest Sports Wife" award for the next 10 years...or until she has a kid. She has also been arrested - beating up the chick that she claims her husband was having an affair with, which makes sense, cause you often see guys cheating on their PMOY girlfriends.

Kara used to work at Disney World as Snow White and Cinderella - talk about giving 12 year old boys a memory that will last a lifetime! She's the first Miss June to win PMOY, a fact that really means absolutely nothing. She's not related to Dancing with the Stars hottie Kelly Monaco, but feel free to mentally picture them writhing around naked, making out on the beach with only you watching.

Christina was one of the finalists in the long-forgotten reality show "Who Wants to Be Playboy Centerfold". Wasn't that the worst line ever created a few years ago, claiming you were a producer for this show? Christina has the distinction, however negative, of being the first PMOY to not be on the cover in the issue she was declared the winner. Sad, just sad.

Sara is currently a senior at Oregon State University, making her officially a Beaver. She's also regularly on The Girls Next Door on E!, and is a personal favorite of Holly and Bridget. Prior to appearing completely naked in magazines, she appeared somewhat naked at Hooters restaurants.