Last Updated on August 3, 2021
1. Drew Barrymore – January, 1995
Nobody has ever used Playboy more perfectly than this. During a stretch of her career that sported titles such as THE AMY FISHER STORY, DOPPELGANGER, and WAXWORK II: LOST IN TIME, Drew had nothing to lose by showing everything she had. She’s never looked back. Hit after hit have followed her for the past twelve years. Thing is, she’s still that sweet little girl from E.T. How a Playboy shoot turns around a career highlighted by being a pre-teen alcoholic and drug abuser is beyond me but somehow it made her more innocent. Kudos to your nudeness Drew.
2. Tricia Helfer – February, 2007
This is the way to do it girls. Don’t even wait for your flame to fade. She knows ‘Battlestar Galactica’ is ending next year. She knows it’s one of the most under appreciated shows of all time. If this doesn’t get you to watch, nothing will. It’s this strike while the iron’s hot attitude that should be noted by all young bouncy women with contracts that won’t last forever.
3. Charisma Carpenter – June, 2004
Speaking of Buffy. As spin-off, ‘Angel’, came to a close Charisma thought she might send out a resume package to all those interested in the form of high quality nudes. Amazingly, that ass hasn’t really gotten her a big break yet. Her hopes of landing WONDER WOMAN seem slim lately and ‘Veronica Mars’ recently died a horrible death but neither would have been a reality without this issue. She shows up in one more family TV movie and I’m going to sue Playboy for her.
4. Kristy Swanson – November, 2002
This is one of my favourites. Just as ‘Buffy the Vampire Slayer’ was completing it’s run of seven ridiculously successful years on TV, Kristy shows up with a vengeance to remind the geeks who started the phenomenon. Sadly, the extremely hot shots did nothing but send her directly to TV and a title on ‘Skating with Celebrities’. In funnier news, Kristy was arrested this year for beating down her husbands ex-wife after stealing him from her (he was her partner on said shit show) while she was pregnant.
5. Shannon Elizabeth – August, 1999
Again, not on the cover. What the shit? Shannon’s actions in the late 90’s were almost unheard of. She burst on the scene by getting naked and masturbating in her first major film role and then jumps to the pages of Playboy weeks later to let us revisit the goodness. In a world where no-nudity clauses still exist, Shannon is a hero. It’s almost as if the timing is all wrong though. Shouldn’t we be seeing her posing naked now, when the scripts are drying up and the breasts are still standing? This isn’t over.
6. Jaime Pressly – March, 1998 & February, 2004
The first appearance worked like a charm, introducing us to one of the hottest rising stars on the planet. The second was just a treat. Jaime used Playboy perfectly and led Hollywood to believe there was nobody else when it came to portraying poor white trash on the big screen (as shown in her film POOR WHITE TRASH). Thankfully, she hasn’t changed a bit and while the movies are pretty quiet at the moment, ‘My Name is Earl’ still delivers her every week.
7. Stacey Dash – August, 2006
It took me an hour to realize she wasn’t the cover girl for her issue as I was searching all over the internet for it. After seeing the pictures all I could think was “How is this chick not on the cover?” One of the most explosively surprising photo shoots I’ve ever seen, it made me go back and watch CLUELESS in a whole different light. It seems to have paid off too. IMDB has her listed for seven projects in the next couple years. Did I mention she’s 41?
8. Teri Polo – February, 2005
“She’s one hot Focker”. Ha ha, who comes up with this shit? Kill them. Tired of taking a backseat to Ben Stiller, Owen Wilson, Robert De Niro, Dustin Hoffman, Barbra Streisand, Blythe Danner, the cat that pees in a toilet, and basically anyone else that appeared in those MEET THE PARENTS movies, Teri decided it was time to shock the world in a surprisingly hot-as-hell spread. If anything it kept her career alive on TV and made sure she doesn’t get written out of the next Focking sequel. I can play too bitches.
9. Denise Richards – December, 2004
Winning the award for scariest cover on this list, I give you D-Rich. After shooting out his kid, Denise was talked into doing Playboy by her proud hubby, Charlie Sheen, to show the world how fast her skin retracts. In the mother of all backfires, Sheen barley had time to put the issue down before receiving the divorce papers. Neither have had a movie worth writing about since. Although, somebody should get the rights to their legal transcripts.
10. Shannen Doherty – March, 1994 & December 2003
Every time Shannen got kicked off an Aaron Spelling-produced TV show she popped up in Playboy. While the first time felt rebellious, leaving her loser friends back in the 90210, the second time had much more of a “look at me, I’m still pretty” feel to it. I’ve always liked Shannen though, ever since she was in ‘Our House’, and can’t help but be drawn to a woman that has actually had the chance to punch Paris Hilton in the face.
11. Tia Carrere – January, 2003
Never reaching superstar status after WAYNE’S WORLD and voicing duties in LILO & STITCH finally led to an amazing pictorial to kick off 2003. Her career has pretty much stayed the same over the years (she still can’t shake that Lilo & Stitch stuff though) and after a brief stint on ‘Dancing With the Stars’, the photos were used again in the German edition of Playboy in 2006. Two career boosts with one shoot?
12. Daryl Hannah – November, 2003
Not having faith in Tarantino’s career resurrection skills alone, Daryl decided to take the comeback one step further by shooting a crazy naked jamboree to promote the film. Seems neither worked. While the 80’s sweetheart has done lots of shit since the KILL BILL volumes, there isn’t a title in the bunch that I’ve heard of (other than SILVER CITY) let alone spent money to see. Don’t worry though, I’m sure there will be a cameo offered in the inevitable remakes of SPLASH, BLADE RUNNER, and STEEL MAGNOLIAS.
13. Vida Guerra – July, 2006
Just when it looked like Vida was primed to jump out of the pages of FHM and onto the acting scene with tiny roles in ‘Chappelle’s Show’ and DORM DAZE 2, she tried to pull the Playboy trick by releasing naked pictures of herself from her camera phone on the internet. Shit seemed to backfire though as she was dropped from her record label (she sings?) over the incident and hasn’t seen a role since. So this time she does it right and gets her incredibly famous ass on the pages of the real deal. Still no roles though.
14. Sherilyn Fenn – December, 1990
This was actually brilliant timing, smack-dab in the middle of promoting ‘Twin Peaks’. Fenn went on to receive Emmy and Golden Globe nominations, made those “Most Beautiful People in the World” list for both Us Magazine and People magazine, and within the next couple years nabbed two of her greatest roles in OF MICE AND MEN and BOXING HELENA. Now you can catch her in THE DUKES OF HAZZARD: THE BEGINNING as Lulu Hogg. Maybe it’s time to visit the mansion.
15. Peta Wilson – July, 2004
I love that the cover says “La Femme Nikita’s Peta Wilson”, like the woman hadn’t done anything since that show went off the air four years prior. Um….. other than showing up in THE LEAGUE OF EXTRAORDINARY GENTLEMEN (this would be far too big a subtitle for the cover) and a couple TV shows, I guess she hadn’t. That’s the point though. Wait until everyone forgets who you are and show up nude. Keep up people.
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