Most Improbable Hookups in Sports History

Amber LeeSports Lists Lead WriterJune 8, 2012

Most Improbable Hookups in Sports History

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    It always creates some major buzz on the interwebs when an athlete hooks up with or confirms a legit relationship with a high-profile somebody. Seriously, the coverage of the dating life of Yankees legend Derek Jeter alone could fill a book. A big one. 

    Derek Jeter hooking up with another stunning, beautiful actress is guaranteed to grab headlines, but not nearly as many headlines as if he were dating someone like Jane Fonda, for example. 

    For whatever reason, many of us like to know all the private-life details of athletes and celebrities. Maybe we're all pathetic losers, but I think it has more to do with morbid curiosity. It's just human nature to gawk at a car crash, as ugly as it may be, and the same goes for ridiculous celebrity couplings. 

    Let's gawk at 15 of the most improbable and ridiculous hookups in sports history. And if you've got the goods on one I missed, lay it on me in the comments section.

15. Serena Williams and Gregory Michael

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    Tennis superstar Serena Williams has dated retired wide receiver Keyshawn Johnson, Knicks star Amar'e Stoudemire, Bobcats forward Corey Maggette and had a three-year relationship with rapper/actor extraordinaire Common. 

    All pretty cool, talented dudes and mostly athletes. So, it came as a bit of a surprise when she was spotted engaged in some serious PDA with actor Gregory Michael, who starred in the televised dumpster fire better known as Greek. 

    Who knows how long the whole thing with this nerdy actor even lasted. Probably not long because Ms. Serena is a bit of a love'em and leave'em heartbreaker. 

14. Lance Armstrong and Ashley Olsen

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    After kicking long-time girlfriend Sheryl Crow to the curb in 2006, super cyclist Lance Armstrong decided it was time to sow his wild oats. Like all of his wild oats. Seriously, every last oat was sowed. 

    Okay, I'm exaggerating a little. But in less than a year, Armstrong was linked to journalist Whitney Casey, fashion designer Tory Burch, actress Kate Hudson and, yes, Ms. Ashley Olsen—of Olsen twin fame. 

    Frankly, I think it's weird when anyone dates an Olsen twin (unless they need the money), and this coupling really skeeved me out.

13. Mike Tyson and Naomi Campbell

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    Despite various allegations of violence and a prison stint for rape, back in his glory days, famed boxer Mike Tyson sure had a way with the ladies. We all know there are plenty of ladies out there with a thing for bad boys, and Tyson definitely fits the bill. 

    His other conquests aside, Tyson's fling with supermodel Naomi Campbell in 1987 was a pretty strange pairing. Mostly because he really went against type for Campbell, who has a thing for aging white dudes with lots of money. 

    But Tyson did have a lot of money back then, so I guess he wasn't too against type.

12. Mindy Lawton and Tiger Woods

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    You're probably wondering why Tiger Woods is on this list at all. His stunning run of philandering included porn stars, sultry cocktail waitresses and various other women that can be bought and sold, like Rachel Uchitel. 

    Obviously there are some moral issues here, but I'm not here to pass judgement on the private lives of others. Whatever, so he bedded a bunch of hot broads. How many of you wouldn't like the opportunity to do the same?

    My issue is his rendezvous with one Mindy Lawton. Seriously dude—a Perkins waitress? This is just too mind-blowing for words.

11. Tom Brady and Tara Reid

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    Patriots superstar/superstud quarterback Tom Brady has dated some of the most beautiful women in the world. Seriously, this dude has dumped girls who are 10-times hotter than almost any girl you will ever meet in your entire life. 

    Brady was linked with singers Mariah Carey and Britney Spears early in his career, porn star Layla Roberts, actress Bridget Moynahan and supermodels Adriana Lima and Gisele Bundchen, the latter of whom went on to become Mrs. Brady. 

    And he also dated Tara Reid. One of these things is not like the other. 

10. Chuck Finley and Tawny Kitaen

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    Why a southern boy hailing from Monroe, Louisiana, like retired pitcher Chuck Finley ever thought he could handle a spitfire sex kitten like Tawny Kitaen, the 80s preeminent video vixen, is beyond me.

    The two were married for what must have been five confusing years for Finley, and the union ended not long after Kitaen faced charges for attacking Finley with the business end of a stiletto heel. 

9. Carmen Electra and Dennis Rodman

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    Most people consider this one of the most improbable hookups in sports history, so I felt it necessary to include the union of wacktress Carmen Electra and former NBA bad boy Dennis Rodman on this list. 

    But I really don't think it was all that improbable. Rodman was an unpredictable clown who never met a bad decision he didn't like, and Electra was a desperate wannabe who obviously recognized an opportunity to grab the spotlight for awhile and seized it. 

    We haven't heard much from either of these two recently. Perhaps they should get married in Vegas again and see if they can catch lightning in a bottle twice. 

8. Dennis Rodman and Jeanie Buss

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    Now this is an improbable hookup starring Dennis Rodman! Did you even know that he and Lakers executive Jeanie Buss had a thing way back in the day?

    She and Phil Jackson have been together since 2001, so it must have been in her wild child Playboy days of the rely 90s. 

7. Monica Seles and Tom Golisano

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    Most of us used to know retired tennis player Monica Seles as the victim of one of the craziest freak-show crimes in sports history. Which, I imagine, actually had to be pretty freaking terrible for her. 

    Maybe most of you still know her for that reason, but I actually know her best as the broad who shares a bed with this very old man. Seles started dating Tom Golisano, the billionaire owner of the Buffalo Sabres, in 2009. 

    Seles was 35 at the time and Golisano was 67. Apparently they're still together, which means Seles is now 38 and Golsiano is now 70. Yick.

6. Deion Sanders and Gabby Reece

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    Beach volleyball goddess Gabrielle Reece and Deion "Prime Time" Sanders dated back in the mid 80s. She was a volleyball player at Florida State, the very same university that a pre-neon Deion attended. 

    That was a lifetime ago, so I don't have any legit details on their relationship. But in 1997, Reece credited Sanders for teaching her the importance and the business of selling yourself and your sport. 

5. Kiana Kim and Pete Rose

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    At this point, nobody should be surprised by anything the disgraced clown of Major League Baseball does. Former Cincinnati Reds player and manager Pete Rose's penchant for betting on baseball earned him a life-long ostracizing from the sport he once dominated.

    And over the years, he has occasionally appeared on television to be his vile self and tell a bunch of lies. But nothing is grosser than ditching his wife of decades for busty naked model with obvious daddy issues Kiana Kim.

    Actually, there is one thing grosser—going on Howard Stern to brag about his sex life with his surgically enhanced plaything. Ew. Ew. Ew. 

4. Alex Rodriguez and Madonna

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    The nation let out a collective "ew" in 2008 when news surfaced that Yankees slugger Alex Rodriguez was dating the aging material girl herself, Madonna. Both of whom were essentially married at the time, but clearly in the early processes of nasty, and costly, divorces.

    Thankfully, this unholy union was only temporary, as most relationships with A-Rod tend to be. They probably had too many arguments about whose turn it was to stand in front of the mirror and gaze at their own reflections.

3. Andre Agassi and Barbra Streisand

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    I bet you just did a WTF double-take. That's right, tennis superstud (well, he was at the time) and Ms. Barbra Streisand got romantical in the early 90s.

    Not much about the couple is known because Babs is famously strict when it comes to disclosing the details of her personal life. But Agassi divulged a few nuggets in his 2009 autobiography—you know, the one in which he admitted to playing tennis while high as a kite on crystal meth.

    Agassi also explained that he met Babs because casino billionaire Steve Wynn coughed up her digits after the two engaged in a gossip sesh on the golf course, in which Agassi confessed he had a thing for Babs.

    So, if you ever meet Steve Wynn, ask him for Kate Upton's phone number.  

2. Marilyn Monroe and Joe DiMaggio

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    I hate to use the term "Beauty and the Beast," because while Yankees legend Joe DiMaggio wasn't exactly a male model, people have been a bit harsh on No. 5 over the years. 

    So when DiMaggio and Monroe married in 1954, they certainly didn't look like an obvious couple to the world. But we all know that opposites have been known to attract, and while the marriage didn't last long, they each considered the other their great love. 

1. Joe Namath and Janis Joplin

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    Back in his glory days, Jets quarterback "Broadway Joe" Namath was pretty much the king of New York. His conquests are legendary and far too numerous to detail, but let's just say he usually went for sultry blondes, but with two major exceptions: Raquel Welch and Janis Joplin. 

    The story of their meeting is detailed here but I'll give you the basics. Apparently, Janis had her manager give Joe a jingle because she wanted to party with the king. Even though she wasn't his type, Joe dug her music and invited Janis to a party he was attending. Janis then proceeded to ply Joe with tequila and coax him into the sack. 

    Say it with me folks! Legen…wait for it…dary!