The 25 Hottest Women from 1990 to 2009 (GIFs and Videos)

Let me start by saying that these rankings were a fucking pain to do. I originally wanted to do a Top 20, but there was just way too much talent in that twenty year span so I ended up with a Top 25 and also cheated with a handful of Honorable Mentions. The fact that I couldn’t even find Honorable Mention room for the likes of Heidi Klum, Demi Moore, or Eva Mendes speaks to how deep this draft class truly is (my first of many sports analogies).

Now, as far as the actual rankings go, the rankings are based on how hot the girl was at her absolute peak. For example, when a group of dudes are discussing the best baseball pitchers of all-time, they don’t just say “Pedro Martinez”—they usually say “’99 Pedro,” because in 1999 he was one of the most dominant pitchers ever. In relation to this list, Eva Mendes would obviously rank higher than Brittney Spears if we’re just talking about how hot they are in general, but Eva Mendes was never as hot as Brittney Spears was in 1999, which is why you’ll find Spears on the list and Mendes left out in the cold. Hopefully this makes sense and I don’t get hate tweets (@jimsveryunusual) for ranking Sloan from Entourage below Lindsay Lohan and Tara Reid.

And lastly, let me B-Rabbitt “I know everything he ’bout to say against me” you guys for a second and point out that I’m well aware that Mila Kunis isn’t on my list, but my research concludes that she started peaking in 2010, narrowly missing the year requirement for this countdown. Onto the rankings.

Honorable Mention: Salma Hayek (1996)

She may not have made the Top 25 but I’m pretty sure she’d be #1 if the list was “Girls You Fantasized About Fucking When You Were 10.”

Honorable Mention: Shannon Elizabeth (1999)

When you’ve got the single most iconic nude scene in recent cinematic history, you deserve inclusion on any list like this.

Honorable Mention: Stacey Dash/Alicia Silverstone (1995)

Hey Chris Berman, stop putting multiple highlight packages together and calling them one top play. But I can’t help it,;I don’t want to ruin my chances of having sex with any of these girls who are way out of my league and who I’ll never meet by not including them in my list they’ll never see. The fact that Stacey Dash was TWENTY-EIGHT years old when she did Clueless makes it totally OK to want to bang her as a high school student.

Honorable Mention: Heather Locklear (1994)

Acknowledging the hotness of Heather Locklear is heterosexually ambiguous, because on the one hand you’re admiring the beauty of a woman, and on the other you’re admitting that you watched Melrose Place.

Honorable Mention: Adriana Lima (2008)

Fully admitting that I probably should have found a spot for 2008 Adriana Lima on this countdown. I fucked up. What do you want me to say? I fucked up.

Honorable Mention: Kate Beckinsale (2003)


The ONLY reason I couldn’t find a place for my wife is that she had no year that stood out to me where she was just dominant. I list 2003 because that’s when the Underworld movies started, but the truth is she’s been a fucking dime since the day she was born and will be until the day she dies. She’s like Karl Malone, never the best in the league at her position but a model of ridiculous consistency. Did I sneaky just say I wanted to marry Karl Malone?

25) Jenny McCarthy (1995)

In 1995 Jenny McCarthy started hosting MTV’s Singled Out, the only game show I ever had to watch with my bedroom door locked. Actually who am I kidding, you can add Dog Eat Dog with Brooke Burns, Strip Poker on USA, and Jeopardy! to that list, too.

24) Jenna Jameson (1996)

1996 was the apex for the porn queen of the 90’s, right at the height of her adult film stardom and right before all that heroin and surgery began to take its toll. I feel like that exact line will be included in her obituary.

23) Cindy Crawford (1993)


It’s hard pointing out when models were at their peak because I don’t have movie roles to go on, but Cindy Crawford is the only girl in history to be the subject of “You’d lick her mole, right?” debates in 1990’s garages and poker rooms across America.

22) Mariah Carey (1999)

I’ll admit this is kind of a personal preference pick, and she may have actually been better-looking earlier in her career, but there was a specific turning point in the late 90’s-early 2000’s where she just started slutting it up in every music video and public appearance and I remember enjoying it very much.

21) Emmanuelle Chriqui (2006)

Definitely the least famous and/or accomplished girl on this list, but ask any guy back in 2006 between the ages of 16-40 who he wanted to marry, and probably 80% of them would say “Sloan from Entourage.” Entourage ended three years ago and I’m pretty sure that percentage is still above 50%.

Pay No Attention to How They Ended Up 5 Years Down the Road Division

20) Tara Reid (2000)

19) Lindsay Lohan (2004)

18) Kim Kardashian (2007)


Tara Reid was actually the inspiration for this entire list because she’s the poster child for someone who was so incredibly hot for a 1-2 year period and then just fell off the face of the Earth after all those drugs and that RIDICULOUS boob job where one of her tits ended up under her armpit and the other was hanging low enough for her to literally titty-fuck herself. Anyway, we won’t hold that against her here. Between American Pie, the sequel, and Van Wilder, she did enough to land a spot next to these other two nutjobs. Lohan gets the nod for Mean Girls, in which I’d rank her the second-hottest mean girl behind Gretchen Wieners, but Lacey Chabert isn’t famous enough to make a list like this. Anyone who says Rachel McAdams was hotter than Lohan in Mean Girls is a fucking liar and is using other factors like Lohan turning into a coked-out lesbian against her.

I’m not sure if I’ll get hate for the Kim Kardashian pick or not, but if you think I should, Google some pictures of her from the late 2000’s and tell me she isn’t one of the hottest women of all-time. Plus, how many hours in 2007 did you spend scouring the internet looking for her sex tape? It was probably more hours than you did anything else besides sleep.

17) Jennifer Aniston (2004)

Given the fact that she’s been delightfully filthy in her last few roles and she’s still as hot as ever, it’s hard to say exactly when Jennifer Aniston peaked, but I went with 2004 because it was at the height of her Friends popularity, and she also had Bruce Almighty and Along Came Polly come out in that year. Every time I saw her on the cover of a tabloid for another guy dumping her, I wanted to just pick up the phone and console her. Not creepy at all.

16) Angelina Jolie (2001)

Hey look at that, Angelina getting the best of Jen again. Jesus Christ, Jimmy you’re a homo. Angelina has always been sexy as fuck, but 2001 was when Tomb Raider came out and I’m pretty sure that was her at her hottest.

15) Tyra Banks (1997)

Tyra’s accomplishments in 1997 included Victoria’s Secret angel, winning Supermodel of the Year, and becoming the first black girl I ever jacked off to.

14) Scarlett Johansson (2006)

Like a couple other smokes on this countdown, it was hard to peg down a specific year for ScarJo, so I went with 2006 when Esquire named her the Sexiest Woman in the World. I bet she’d make just as much money as a phone sex operator as she does an actress. Probably the sexiest voice in the world. The only issue is you can’t see her tits through the phone.

13) Megan Fox (2007)

Off the top of my head I can’t recall a bigger “Wow who the fuck is that?” moment than when Megan Fox first appeared on screen in Transformers.

12) Beyonce (2004)


Beyonce is still busy being hot these days, but back in 2004 she was at the top of her music video game and ugly ass Jay-Z had yet to enter her.

11) Britney Spears (1999)

I have no stats to back this up, but I gotta think that when the “Baby One More Time” video came out, internet searches for “schoolgirl porn” went up around 10 trillion percent. She had a relatively short run at the top, and was unfortunately less slutty at her hotness peak than her slighty-less-attractive rival Christina Aguilera, but good lord those first few music videos.

10) Tiffani Amber Thiessen (1992)

Went with 1992 for Kelly Kapowski because Saved By the Bell was a few seasons in at that point and as each episode went by it was less and less creepy to wanna marry a high school kid. It’s an absolute shame that a Zach/Kelly sex tape never hit Bayside.

9) Jennifer Lopez (2000)

Last week I “accidentally” watched American Idol and she might be the hottest 40-something this side of Beckinsale, but back in 1999 she put the JLO in “Jesus, I’d LOve to just smell her.” The green dress she wore at the 2000 Grammys is the equivalent of Babe Ruth’s 1927 Yankees jersey.

8) Carmen Electra (1997)


They said you couldn’t possibly upgrade on Jenny McCarthy as the host of Singled Out, and then they went and replaced her with Carmen Electra. She also made watching MTV Spring Break mandatory for me over going outside and playing with my friends.

7) Brooke Burke (1998)

Brooke Burke was my first true celebrity crush. Think about how awesome the format for Wild On was, too—just a ridiculously hot chick going to different places around the world to party and lay on beaches. She was basically the Rosa Parks for girls like Devin Brugman and Natasha Oakley, who make a living doing the same thing today.

6) Halle Berry (2001)

No trouble picking the year here: 2001 is when both Swordfish and Monster’s Ball came out. In case you’ve been hiding in a cave or are just really fucking weird, she gets naked in both of those.

5) Jessica Biel (2001, 2007)

This is the only girl on the countdown I literally couldn’t put a specific year on, so I went with two. 2001 was when people started realizing that the oldest daughter on 7th Heaven was kind of a smoke, and then she came out with Summer Catch the same year and just obliterated her wholesome, pretty-but-not-sexy reputation. Then in 2007, she has the ridiculous ass GIF in I Now Pronounce You Chuck and Larry, gets naked as a stripper in some other shitty flick, and gets named Sexiest Woman in the World by several notable publications.

4) Pamela Anderson (1995)

Arguably the girl of the 90’s, in 1995 Pam was busy starring in one of the most popular shows in television history, some shitty-side projects where they only hired her because of her looks, and a home movie in which she deep throats then enormous penis of her famous rocker husband who she had known for four days. Quite possibly the most famous tits of all-time.

3) Jennifer Love Hewitt (1998)

Did somebody say tits?

2) Jessica Alba (2005)


Ask the same guys from that Sloan hypothetical the same question one year earlier, and maybe 90% are going with “Jessica Alba.” Alba is an awful, awful actress, but I also don’t think I’ve listened to a word she’s ever said. Incredible that she’s #2 on this list but that she wasn’t even the hottest Jessica from that year.

1) Jessica Simpson (2005)

I know she’s flirting with the Reid/Lohan/Kardashian ended-up-a-trainwreck division, but I’ll defend this pick to the death because I don’t think a woman can possibly look hotter than Jessica Simpson did in Dukes of Hazzard. Face? Check. Legs? Check. Ass? Check. Tits? Fucking checkmate. She may have been the most annoying girl on TV until the Kardashians came on a few years later, but honestly if you didn’t watch The Newlyweds with her and Nick Lachey just because it was an awesome show of how hot she was, I don’t respect you as a man.

Jimmy T is a regular columnist for BroBible. He runs the blog Jimmy’s Very Unusual.