15 Celebrity Men Who Dated Out of Their League (How The F Did These Average Joes Score These Hotties?)

15 Celebrity Men Who Dated Out of Their League (How Did These Average Guys Score These Hotties?)

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-Z

Dude 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 Anthony

Though 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 Manson

We’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 Hefner

There 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 Rock


The “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 Doherty

There’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 Simmons

Uncle 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

Yes Kim K. is all levels of foul for how she played Kris Humphries, but the fact still remains that when Humphries hooked up with the biggest Kardashian he traded way up.

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.

14. Ryan Seacrest

Ryan Seacrest’s bank account must be pretty fat to have snagged Teri Hatcher.

  • Lola

    Please add Swizz Beatz to the list. I will never understand why Alicia Keys settled for that big beaked loser.

    • S

      Because Swiss probably layed that hammer down on Alicia plus Swiss ain’t broke kat. He got money….believe that.

    • I can’t believe they didn’t mention the dead-ugly Lyle Lovett who was married to Julia Roberts for a while.

  • ja

    Did not know Russell Simmons dated Cynthia Bailey of Atl housewives. Think on one episode it was revealed they had been engaged.

  • ja

    Russell simmons dated Cynthia Bailey also, think they were engaged…who knew?

  • Bkelley

    Money.+ Fame+ Power. That’s how. These men aren’t average Joes.

  • melissarose10166

    Seal’s scars on his face is caused by lupus, a medical condition.

    • disqus_bwVSCHoDOx

      so what?

    • Ken Jones


  • Janay

    Women who are dimes settle for ugly men far too often these days. Many women do It out of fear that the cute men will play them. Low standards has the dating game all messed up these days. Ugly guys are getting so much attention lately that they TOO are @zzh.0les. It’s a sad day when gucci mane or lil wayne standards are higher than they women they date. The decisions we as women make, determines how men act. I am not asking for too much if I say I want an attractive, guy who treats me well. Janet was with ugly af JD and he still dogged her out. Her new man is way finer and treats her better. Just remember these men out here are getting pickier and pickier with their standards, so by you women getting less and less picky with your standards you are only hurting yourself and its messing up the whole dynamics of the dating game.

    • @iSweet_Love

      Looks doesnt always matter. You could be the most gorgeous person in the world, but if you have a bad personality it can make you look ugly as ever. If the person doesnt fit “society” version of good-looking yet has a good heart, then I dont see how its lowering standards…

    • Ken Jones

      At least your honest. Many girls say ‘I just want a nice guy.’. Spare me.

  • doesn’t matter

    GTFOH! Jayz is the man is his own right….Beyonce was definitely out of his league.

  • absofsteel10

    money talks…If they didn’t have it. They wouldn’t get the girls.

    • EricCartman1st

      Exactly , money for women is the equivalent of beer goggles for men .

  • S

    When you mention Jay Z you must be talking about looks because Jay is Diffenently in B’s league as far as money is concerned. And when people say Average Joe! I think each and everyone of these chicks was average Janes at one time or another too. So what’s your point? Sound like a bunch of broke a$$ judges to me.

  • S

    That goes to show you that even if you have looks you can still be a cornball same as having money. No Homo! but Biggie might have been the best looking kat but he was a real dude and chicks probably liked his personally and its not just because he was no dam leader in no ghetto either.

  • Allen

    Where is Tom Green and Drew Barrymore?

  • It’s all about the MONEY !!!! Duh…..

  • michelle knight

    What ever happened to Beauty being in the eye of the beholder! I personally find every day average Men to be just as & in some cases much more attractive than many entertainers or guys in the public eye! Yes, sometimes it is about settling, but then sometimes it’s about, “The Beauty being in the eye of the Beholder”, point blank period!!!!!

    • Fumetti666

      But Marilyn Manson? Come on. Don’t you want good looking babies who grow up into good looking men and women?

    • Bette Tetreault

      Michelle, you took the words right out of my mouth…and women are not as shallow they are made out to be.

    • Michelle I agree, but come on, these men aren’t looking for women on a equal footing. H.H. R.S, they are loaded it is the fairytale prince and since some of these women were models I doubt their mom was a doctor. I’d like to see the past boyfriends of the women and see if there’s a ring of truth. It is a give and take, llike Donald’s wife said, when asked if she married for money she said, do you think he would have married me if I wasn’t so beautiful. It is a trade off it just speaks of the character actions speak louder. I bet there ‘s a prenup , like true love

    • jxs9

      That’s just something ugly people say.

  • yoyoyo

    The answer is right in the headline…celebrity!

  • bpai99

    Is it possible that money and celebrity had anything to do with it?

  • tom hulsey

    out of their league? all bimbos!!!

  • lk

    David Arquette and Courtney Cox… ???

    • David Dietsch

      I agree.

  • DC

    Bachelor Bob Guiney with the Rebecca Budig. She’s way hotter!

  • jxs9

    Are you kidding me with this?What kind of reporting is this?How does Huff Hefner get all those girls. Obviously the women are attracted to guys that can be their grandfathers. Its obviously money and what he can do for their “career”. Same with the rest of these douchebags. They’re rich and/or famous.

  • earthbound

    The only people who think there are “leagues” in dating are people that are unhappy with their SO’s.

  • Hotties ? With makeup, women look like clowns; without, they bear the damage of makeup.

  • iknowiknow

    Is that “young blond vixens” or “victims” with Hefner?

  • iknowiknow

    This site is too slow and annoying. I give up.

  • Jason

    How? They are rich celebrities….horrible title for this article.

  • UK Lady

    oh please! it’s all about money, power and fame. nothing surprising here. it’s just the way life goes. although, i do think that when good looking women stray past 35 and wanna settle down then they’ll tend to settle for the ‘not quite there guy’. i think that is what happened to janet and pamela anderson and jennifer lopez.

  • topcatt

    Money get the girls, but money doesn’t get you total happiness.

    • Ken Jones

      Wanna bet? Depends on what you want out of life.

    • hallas

      I am never more happy than when I have money in my pocket, sorry but money does make me totally happy!

  • yolo


  • Vencenzo

    Give me a break… Kim Kardashian & Pamela Anderson are like door knobs, everybody gets a turn! Stop glamorize GOLD DRIGGERS!

  • Mike

    What about Julia Roberts and Lyle Lovett? Never figured that one out, but the dude must be hung like a horse.

    • ddbandit

      That one’s a bigger mystery than anthing on this list BY FAR !!!

  • Even though neither of them were huge stars when they were together, I always wondered what attracted Angelina Jolie to Billy Bob Thornton.

  • ouchcat

    Women have cosmetics to attract men, men have Porsche.

    • Ken Jones

      Ha! Well said.

  • commonsense

    Can you say … MONEY … ?

  • fahqueue

    I wouldn’t call any of the guys on this list “Avergae Joes”. Really? Multi-millionaire rappers, rock stars, magazine publishers, actors count as “average Joes”?

    • LYRICS

      the term is used “lightly”….in terms of the looks department they’re considered ‘average”, but in my opinion A LOT of these men are BELOW “AVERAGE” AND ONLY GET PLAY B/C THE GOT $$$$$$$!! Maybe they’re personalities are stellar, that’s the only logical explanation!!!

  • grep

    Hugh Hefner basically runs a brothel. No secret there.

  • Maryland MJ

    Looks aren’t everything.

  • Veratta Pegram-Floyd

    I disagree about Eric Benet…

    • YouGotsToBeKidding

      Yuck! Not even…

  • everywoman

    Bobby Brown should have been #1

  • Jay-Z may not be all that good looking but he can defiantly get it! You know he can pop some good game.

  • guest

    jerry o’connell, the fat kid from Stand By Me and Sliders, married victoria secret model and movie star rebecca romijn

    • Ken Jones

      What part of money and fame don’t you get?

    • Jabrone

      But he grew up a good looking dude.

  • Billy Bob

    Russell Brand anyone?!?!?! Plus Katy Perry was way richer? What up with that???

  • jpbrody

    I’m curious, but I’m not going to click through 11 pages of slides . . . I know styleblazer needs the ad revenue, but goodness . . . my life is worth more than that.

  • PM

    Marilyn Monroe> Joe Dimago, Arthur Miller???

  • OMGDuh

    With the exception of a couple of those dude – it’s obvious – they’re LOADED. Duh.

  • Ken Jones

    Money, money, money!


    ummmmmm don’t u mean Fantasia was “out of her league”!!!???? Tasia ain’t cute….@ all!!! Cook isn’t “gold” in that department either, but he can get waaaaaaay better lookin’ women than that “hood chick”

  • Mandy

    Im sorry and I am just gonna throw this out there. The Penis Size and or the way they are in bed. Could be one of the factors Duh? lol

  • Mandy

    Ryan Seacrest snagged Julianne Hough now

  • Anonymoose

    This article was utterly ridiculous. I mean come on, are you telling me you don’t know why Hefner constantly has a gaggle of blonde clones around him? And none of these men are “average”. They all have one very obvious thing in common. Plus, Russell Brand is way, WAY out of Katy’s league. He should not be on this list. Don’t know how he settled for her, even for such a short time. That poor man. (Well, not literally, of course)

    • LenMe

      Seriously? Russell Brand? You need to get your eyes checked.

  • Single biggest omission: Geoffrey Arend landing Christina Hendricks. Wha-what?

  • I never heard much about these two. It was they were dating, moved in together. I don’t know when they broke up.

  • Really I think Jennifer was the lucky one she has been had by all and kept by none.

  • Jill

    It’s not that unusual for a woman to date a dorky guy. If you want to write an interesting article, write one about a woman who dates out of her league. Where the dude is hotter than the woman.

  • Shimm

    As if dating a man for money is any worse than dating a woman because she just happens to be beautiful. How would a woman even prove she’s not a “gold digger”? I want a partner who is a good provider. Am I a gold digger? What, am I supposed to date some toothless, homeless loser just so all you haters won’t call me a gold digger?

  • Me!

    I’m calling foul on Fantasia and Antwone. He is clearly the better looking of the two.

  • crazyinlove

    I wonder why Ryan Seacrest went twice instead of putting Heidi Klum and Seal… Just saying…

  • xSassySusiex

    Follow the money.

  • ellen

    Do we really need “the f” in the title of this article?? How about just “How Did These Average Joes…”?

  • In the real world most of these guys e.g., Russell Brand couldn’t get laid in a whorehouse with a pocketful of $100.00 dollar bills. And some of these skanks e.g., Fantasia, couldn’t get laid on a troop train.

    • hallas

      You’re insane. Most of these guys would have no issue getting ‘laid’. Hef was a hottie in his prime and Ryan Seacrest? I’d pay for him to lay me down! 🙂

  • LenMe

    What’s wrong with Ryan Seacrest? He’s cute. Most women like men who are confident and make them laugh. Others are just gold diggers.

  • Lee Washington

    Money,, Money,, Money. Fame,, fame,, fame,, photo ops,, etc. Plus how many chicks can the average guy take on an around the world criuse. Plus Fantasia should pay anyone to date her.. uuugghhh

  • ModeratesRule

    I will never get how Marc Antony got together with J Lo, she is so drop dead gorgeous and could have had any well-off Latino or anyone else she wanted (still can).

  • ModeratesRule

    Also, a number of these women are wealthier than the guys they are with, so I would hardly call those women gold diggers….

  • and janet the blob is desirable to whom?

  • layla

    Just curious as to what’s wrong with Ryan Seacrest? He’s cute and obviously extremely intelligent in his many pursuits. I think he’s been trading down with the women he’s been romancing. Also, Eric Benet may be a dirtbag; ugly, he’s not.

  • hallas

    Russell Brand is cute in his own right/ways.

  • True Story

    lol most of these guys are AT LEAST just as attractive as the women

    whoever wrote this must be unaware of the existence of makeup

  • phreakincool

    Stupid-azz author. How’s the haterade? I give props to all of these dudes for bagging these babes.

  • Darth Rant

    I don’t know the other two names, but Kate Moss is hideous. I don’t know how she’s considered a model, unless it’s true that models are chosen because they “photograph well” – whatever the fu*k that means. I mean, I’ve seen commercials with her; the lens does not love her.

  • kevin close

    Pamela Anderson is into those that are “hung like donkeys” LOL!!

  • Sith Lord

    Sorry, Pete Doherty and Kate Moss are perfect together: they’re both hideous! He looks like the junkie he is, and I don’t know how on earth she became a model, let alone a supposed “super-model.” I don’t know the other women mentioned, but if they look as “good” as Kate, ’nuff said.

  • Sith Lord

    And Russell Brand… yikes! What were you thinking, Katy?!

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