Things only seemed to get tougher for Playboy every year in the 2000s. As a result of all the free Internet porn and the popularity of more hard-core stars like Sasha Grey and Faye Reagan, the magazine hemorrhaged money throughout the aughts, causing the press to speculate that the publication would go bi-monthly or even quarterly in the upcoming decade.

Nowhere is this problem more evident than the covers from the year 2000, which could easily have run in the 1960s or 1970s, just based on their style. For example, the January cover looks like an acid trip through Berkeley; April stars Bijou Phillips, daughter of the Mamas and the Papas bandleaders; and the photos with Chyna and the Bentley twins reveal fashion choices that worked better 10 or 20 years earlier.

Luckily, June 2000 cover girl Jodi Patterson is the only era-appropriate choice the editors made that year. Paterson, best known these days as Mrs. Michael Andretti, is one of the only Playmate of Year cover girls we've featured in these lists. She wins out here because of that lollipop -- obviously.


This was a tough one. In spite of the fact that almost all of the 2001 covers appear to have been designed by a coked-out photo editor trapped in the '80s, two stood out as genuine classics: One features a model named Angelica Bridges in a see-through top that prevents us from featuring the photo here.

But even more ridiculous was the September 2001 cover, featuring "Survivor"'s Jerri Manthey. Good Lord, it seems like 400,000 years since Matheny was a "celebrity" and people actually watched that show. And while Manthey finished a disappointing eighth in that year's Australian competition, she always came first in our pants. Or something.


We wish all of the copies for the January 2002 issue died in a fire, if only to get rid of that unspeakable heinous cover for Chyna's second appearance in the decade.

Luckily, almost every cover the rest of the year is a smash -- from Tiffany's teasing appearance in April to our childhood crush Kristy Swanson in November and current crush Dita Von Teese in December, the magazine finally had a decent year.


Tia Carrere, Clint Eastwood's daughter, Carmen Electra, Sarah from that "Joe Millionaire" travesty, the girls of Starbucks, Daryl Hannah and Shannon Doherty ... all in one incredible year for Playboy. How the hell do we choose from that lineup?

By picking the weird ringer, Dora Kerchen, the cover girl for the March 2003 Latin Ladies issue. Come on, she's wearing a ridiculous outfit that barely covers any of her body, let alone the goods.

She's also the only Playmate we've ever come across to be deported from the United States, so she's kind of a badass. According to several sources, the TV presenter, also known as Dorisma, is contesting this claim using the defense that her sexy body should earn her residency in the country as an "alien of extraordinary ability." Seriously.


It would be tough to live up to the standards of 2002 and 2003, but for Playboy's 50th-anniversary year, at least they brought out the star power: Jamie Pressly, Denise Richards, Pamela Anderson and Rachel Hunter all graced the covers of 2004 issues.

The winner this year, though, is a total nobody: a woman named Evelyn Gery, who graced the October 2004 cover and now barely even comes up in a Google search. She was either a cheerleader or just a plain ol' UNC bombshell. Either way, we'll picture her on the sidelines in a skimpy blue-and-white uniform, practicing her school spirit without any panties.


Whoa -- why didn't anyone tell us that this major hottie, Teri Polo, who was the February 2005 cover girl, was in that dumb movie "Meet the Fockers"? We might have even watched the first one, just to catch a glimpse of some PG-13 hotness.


Meanwhile, the rest of 2005 featured Paris Hilton, Bai Ling in the worst S&M get-up imaginable, and Marilyn Monroe all covered up. Luckily, there's also the August 2005 cover, one of our all-time favorites, featuring that naked chick from "Wedding Crashers," Diora Baird, doing her classic Emma Peel impersonation with maximum boobage. They're mostly covered up, but it's probably for the best that we can't see all of Baird's breasts -- the shock of witnessing them in all their free-flowing glory might cause us to hyperventilate or even believe in God again.


Adrianne Curry, that year's It Girl and winner of "America's Next Top Model" and Peter Brady's heart, would have been a fine choice to highlight this year in review ... oh, but Jessica Alba came along in March 2006 and stole the show.

There's nothing particularly interesting or unusually sexy about this cover -- other than Alba's presence, of course. Seriously, guys, if I had awarded the 2006 prize to anyone else, you would have gone mental on me, wouldn't you?


Ah, now this is more like it: a surprisingly appealing shot of Pamela Anderson leading the January 2007 issue ... Mariah Carey and her ridiculously fake but nonetheless appetizing boobs on the cover of the March 2007 edition ...

And best of all, "Battlestar Galactica"'s Tricia Helfer tore off her Cylon suit for the February 2007 Playboy. And we must have been good little boys that year because we even got a butt crack tease from Ms. Helfer. With photos like these, it simply doesn't make sense that this show isn't permanently affixed to broadcast television's lineup.


No wonder Playboy only made news for its financial woes last year: just perusing over its covers for 2008 is enough to make you dump all your stock and shift it all to Worldcom. For starters, Anna Faris is totally overrated as a sex symbol and Carol Alt is currently overrated, period.

But holy jumpin' Jesus on a tricycle, here comes Ashley Harkleroad, the then-23-year-old tennis star who got all oiled up and sexified for the August 2008 issue. What is it about a woman with a perfect body, bending over, smiling mischievously, holding something of a phallic symbol, and wearing a short skirt that turns us on so much? All of it, damn it.


We're going to say no to almost all of the covers from this year. Enough with boring fake celebrities like Holly Madison and Aubrey O'Day. No to looking at Seth Rogen, thanks, and a big no to Heidi Montag covered in figurative dirt and whatever else. And a hesitant no on seeing Marge Simpson in the buff, which reminds us of all that creepy fan-created porn for anything that ever becomes popular.

If we have to choose one cover to like out of all of these, we'll reluctantly pick the one starring Tuuli Shipster and Kiera Gormley as lesbian vampires in October 2009. You know, for the lesbian-vampire-sex factor.