When you're an average guy in everyday life, you may not have a ton of luck with the ladies. However if you're an average dude in terms of looks in Hollywood, you just might snag the hottest chicks in the game. Here's a look at nine celebs who seem to have dated out of their league. But if we were to keep it real, we suspect their good-looking wallets helped seal the deal for some of these guys. Check it out...
1. Jermaine Dupri
The world did a collective mouth-drop when it was confirmed that the pint-sized rapper, producer, and songwriter was dating Janet Jackson. Though the two were head over heels for each other, their relationship was on-again and off-again for eight years until they parted ways in 2009.
2. Jay-ZDude might have "gotten his swagger back" but the camel jokes were rampant when it was revealed circa 2002 that he was dating the über gorgeous Beyoncé.
3. Marc AnthonyThough many would agree that Marc looks like a latin Skeletor, papi has had a string of incredibly gorgeous women under his dating belt. Notably, ex-wives former Miss Universe Dayanara Torres and acting/singing sensation Jennifer Lopez.
4. Marilyn MansonWe've seen no receipts to prove that Manson is actually human, but that didn't stop hotties like Dita von Teese and Rose McGowan from dating the rocker.
5. Hugh HefnerThere must be some mighty potent little blue pills available only at the Playboy Mansion. Sure he's charismatic, but how else could Hef be snagging all these young blonde vixens?
6. Kid RockThe "American Bad A$$" singer sort of resembles Pinky from "Pinky and the Brain," but that didn't stop him from snagging beauties like Pamela Anderson or Jamie King.
7. Pete DohertyThere's no telling what Pete said to bag babes like Kate Moss, Canadian model Irina Lazareanu, and South African model Lindi Hingston, but it sure worked. The odd-man has been linked to all three ladies.
8. Russell SimmonsUncle Russ may have man-boobs, but the media mogul is never short of gorgeous women to date: ex-wife Kimora Lee Simmons, Denise Vasi, Porschla Coleman, Melissa George—just to name a few.
9. Biggie Smalls"Heartthrob never, black and ugly as ever"...hey, he said it himself. Perhaps it was the Coogi down to the socks, but women sure did love them some Big Poppa: Faith Evans, Lil' Kim, and allegedly Charli Baltimore.
10. Eric Benet
This pair had people side-eyeing megastar Halle Berry from the start. And when this fool had the nerve to cheat on her, it confirmed what everyone had thought from the start—Eric Benet didn't deserve her.
11. Kris Humphries
12. Antwone Cook
Antwone "Nobody" Cook has managed to make singer and Idol Winner Fantasia an even hotter mess, while embarrassing her publicly.
13. Russell Brand
Cutie Katy's relationship with the Shirley Temple curl-wearing "comedian" had everyone on pause.
15. Ryan Seacrest, Again
Julianne Hough's main claim to fame is "Dancing With The Stars," but the perfectly tanned blonde still probably could've pulled a bigger Hollywood hunk.-Danielle Gray
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