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The 30 Hottest Fans of the Kentucky Derby

Scott HowardContributor IMay 4, 2011

The 30 Hottest Fans of the Kentucky Derby

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    Jeff Gentner/Getty Images

    The Kentucky Derby is this weekend, and it's one of those events that draws fans from all walks of life. Luckily for us, some of the fans are extremely hot women.

    Whether they're horse racing fans or not, celebrities come from far and wide to enjoy the Derby (and its pre-parties and after-parties).

    All the women compete to see who can have the most extreme hat, yet somehow they continue to look great.

    Here are the 30 hottest fans of the Kentucky Derby.

30. Ashlee Simpson

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    Never has plastic surgery worked out so well for somebody. Ashlee Simpson went from Jessica's little sister to a bona fide hottie after getting some work done on her nose.

    Here she is with then-husband Pete Wentz from Fall Out Boy, but Simpson filed for divorce in February 2011.

29. Brooke Shields

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    Jeff Gentner/Getty Images

    Her heyday may have been in the '80s, but Brooke Shields still knows how to look hot at the Kentucky Derby.

    I'm not positive if the hat was inspired by her movie Blue Lagoon, but I'm pretty confident.

28. Heidi Montag

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    Jeff Gentner/Getty Images

    Here's a happy, pre-surgery Heidi Montag at the Derby. I'm sure that withdrawal from the happiness of the Kentucky Derby made her depressed and turned her into this.

27. Chilli

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    Her real name is Rozonda Thomas, but you probably know her as Chilli from the '90s R&B girl group TLC.

    Even though she hasn't made music for a while, she's still a welcome sight at the Kentucky Derby.

26. Bethenny Frankel

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    Jeff Gentner/Getty Images

    She may be on Real Housewives of New York, but in 2009 Bethenny Frankel was in Kentucky for the Derby.

    She looked good, but she probably got kicked out for having a catfight with another cougar in the stands.

25. Laura Prepon

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    A. Messerschmidt/Getty Images

    Actresses come out of the woodwork when it's time for the Derby. That '70s Show star Laura Prepon doesn't do much acting these days, but she was sure to be seen at the pre-Derby party the night before the big day.

24. Jennifer Love Hewitt

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    I know what Jennifer Love Hewitt did last spring: went to the Kentucky Derby. She seems really happy to be there, so we'll likely see her again this year.

23. Kym Johnson

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    The Dancing with the Stars dancer/coach made an appearance at the Derby with her trainee Joey Fatone.

    I thought about cropping him out, but hey, good for him.

22. Danica Patrick

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    Danica Patrick is used to automobile racing, but she's willing to watch the horses run around as well.

    Just look out for her coming around the corner in her car while the horses are running down the home stretch.

21. Gretchen Wilson

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    Gretchen Wilson is a country music star who's not afraid to show it off. Here she is at the Kentucky Derby with a modified cowboy hat, something she's used to wearing all year.

20. Gabrielle Union

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    Jeff Gentner/Getty Images

    The Derby is the place to be seen for athletes and their significant others. Dwyane Wade brought his girl, Gabrielle Union, to the Derby in 2008.

    No word on whether she broke out an impromptu cheer in the infield.

19. Diane Lane

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    Diane Lane is the reason that men in their mid-20s line up to see movies like Under the Tuscan Sun.

    She's a classic beauty who, like a fine wine, only gets better with age. She's just the type of hot older woman you're going to see at the Derby.

18. LeAnn Rimes

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    You would expect to see country singers at an event like the Kentucky Derby, and LeAnn Rimes certainly doesn't disappoint.

    This is one of the larger hats that we've seen...feel bad for the unfortunate guy sitting behind her.

17. Molly Sims

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    Molly Sims is an actress/lingerie model who puts on some more clothing when she heads out for the Kentucky Derby.

    So classy.

16. Jenny McCarthy

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    Most of you probably remember her from her days as co-host of MTV's dating show Singled Out, but McCarthy has also acted in some other stuff...probably.

    No matter how she's keeping herself busy these days, she's always welcome at the Kentucky Derby.

15. Rebecca Romijn

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    Rebecca Romijn is an actress/model known for her work in the Sports Illustrated Swimsuit Edition and her role as Mystique in X-Men.

    Here she shows off her extravagant hat at the Derby.

14. Eva Marcille

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    Eva Marcille won season three of America's Next Top Model, and she's not afraid to do some modeling on the red carpet at the Kentucky Derby.

13. Jefra Bland and Maria Montgomery

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    You can always count on the Kentucky beauty queens to show up at the Kentucky Derby. Here we have Miss Teen Kentucky Jefra Bland and Miss Kentucky Maria Montgomery.

    It's kind of like having to drag your little sister along...if your little sister is a fellow Beauty Queen.

12. Vanessa Minnillo

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    Nick Lachey is always at the Derby, so we're sure to see his significant other. First it was Jessica Simpson, and now it's Vanessa Minnillo, so we certainly won't be disappointed this year.

11. Paris Hilton

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    I'd guess that Paris Hilton isn't the biggest horse racing fan in the world, but she sure loves picking out hats for the Kentucky Derby.

    Do you think she said, "That's hot" when she picked it out?

10. Tara Conner

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    The disgraced Miss USA and Miss Kentucky 2006 showed up in 2007 before the controversy over her drinking and drug use started.

    Hopefully she's clean and will be coming out this year.

9. Jessica Simpson

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    Remember when Jessica Simpson used to be in the news? I do, and when she looked like this we couldn't wait to see her.

    Not sure if she'll show up with fiancé Eric Johnson this year, but we hope so.

8. Nancy O'Dell

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    Access Hollywood hottie Nancy O'Dell tries on her Kentucky Derby outfit before the big day. I've never understood how the people sitting behind the women wearing these hats can see anything.

7. Maria Menounos

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    Maria Menounos is another one of those celebrities where you're not quite sure why they're famous. We don't really care, as long as she keeps showing up at the Derby looking like this.

6. Marisa Miller

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    Although we're used to seeing her in much less, Victoria's Secret model Marisa Miller still looks stunning in her classy Kentucky Derby outfit, complete with huge hat.

5. Kim Kardashian

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    Jeff Gentner/Getty Images

    Kim Kardashian would never miss the opportunity for some publicity, and here she is at the 2009 Kentucky Derby, complete with oversized hat.

    I wonder if she even knew that the Kentucky Derby was a horse race.

4. Kendra Wilkinson, Bridget Marquardt and Holly Madison

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    Jeff Gentner/Getty Images

    Back when they were still dating the Hef-meister, the Girls Next Door wouldn't miss the opportunity for some fun in the sun.

    We'll see if Hef shows up with his new girlfriend this year...scandal.

3. Petra Nemcova

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    Paul Hawthorne/Getty Images

    Petra Nemcova is a swimsuit model and a contestant on Dancing with the Stars who has been known to make an appearance at the Kentucky Derby.

    We'll all be on the lookout for her this year.

2. Jaime Pressly

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    Jaime Pressly is an actress best known for her appearances in Playboy and her Emmy-winning performance in My Name is Earl (seriously...she won an Emmy).

    Pressly is always a welcome sight at the Kentucky Derby—especially in outfits like this.

1. Beautiful Mystery Woman

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    The best part about the Kentucky Derby is that sometimes the celebrities aren't even the hottest women there.

    That's why this random Derby hottie takes first place. If anyone knows who she is, please let her know so that she can come claim her prize.

    Thank you.

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