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The 25 Biggest Pretty Boys in Sports

Todd BoldizsarAnalyst IJanuary 17, 2017

The 25 Biggest Pretty Boys in Sports

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    This article could just be pointing out the obvious, but here are the guys that still love to be pointed out. These athletes go out of their way to get their hands, hair and wardrobe up with the latest fashion trends, seizing every opportunity to bling for the camera.

    Surprisingly, many of them are football players, but maybe that's why they try so hard when not wearing a helmet or suited up. Others, like soccer players and baseball players, are more of the variety we would expect for this type of countdown.

    Without further delay, here are The 25 Biggest Pretty Boys in Sports.

Honorable Mention: Rickie Fowler

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    Scott Halleran/Getty Images

    This guy's long locks and trademark ability to avoid making eye contact with the camera lands him an honorable mention on the countdown.

    Fowler fully realizes when he is on camera, and in a sport where absolute silence is requested, he makes sure he's loud in all the non-audible ways.

Honorable Mention: Keith Hernandez

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    Believe it or not, the jacket Hernandez is wearing in this photo was actually in style in the late '80s and early '90s. Hernandez was the poster athlete when it came to style in baseball, so much so that it earned him a guest spot on Seinfeld. 

    The episode featured Hernandez as a pretty boy baseball player Jerry was trying to impress and Elaine was falling for. The show only fueled his ego, and now he's doing Just for Men commercials. Talk about reaching a pinnacle...

25. Adam Vinatieri

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    The Colts placekicker epitomizes the pretty boy kicker. Maybe the sissy fits rubbed off Tom Brady in Boston while Vinatieri was kicking for the Patriots.

    Now with the Colts, Adam rarely needs his helmet while the team scores touchdown after touchdown, exactly the pace he needs to show off from the shoulder pads up.

24. Jose Theodore

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    The top of Theodore's rap sheet includes being dumped by his girlfriend after being caught on video with Paris Hilton. 

    And according to CTV, that's not the least of his pretty problems:

    "It's been a rough year for Theodore all around. Besides the most recent developments in his personal life and the premature birth of his daughter, he tested positive for Propecia, a banned substance, earlier in the season.

    "Adding insult to injury, the Canadiens' team physician told reporters Theodore had been taking the hair growth drug for eight or nine years."

    What NHL netminder do you know that needs strong, full hair under his helmet to stop shots?

23. Alexandre Daigle

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    Listed as one of the biggest draft busts in NHL history, Daigle burst on to the scene in 1993, but never amounted to anything more than a ‘90s pretty boy with the “curly top” hairstyle that for some reason was very popular in that era. Looks like a mop on top of a Q-tip...

22. Reggie Bush

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    While you could argue most of his pretty boy image comes from dating Kim Kardashian for too long, Bush still makes sure single ladies notice him off the field.

    But where do you go after dating Kim? Probably to the doctor to get some kind of vaccine.

    We could add Miles Austin to this list as well, but he's just a Bush accessory at this point.

21. Manny Ramirez (Off the Field)

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    While Manny seems sloppy in his uniform, he is actually quite the snazzy dresser on the streets. And why not? With that extra $20 million he’s getting from the Dodgers for essentially…nothing…he should have a few extra bucks for designer suits and bottles of Clicquot.

20. Paul Pierce

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    There are many different breeds of Pretty Boy. For example, Paul Pierce. I have no idea what’s going on in this photo or what the hell he’s wearing, but I can tell you that he always dresses to impress…somebody.

19. Carson Palmer

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    It’s hard to emerge as a Bengal these days, but Carson Palmer definitely fit the bill while at USC. It seems the Trojans are breeding grounds for pretty boys who have grown up just a little too close to Hollywood. 

18. Roger Federer

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    Tennis certainly has its fair share of metros, but Roger Federer is one of the biggest names in that group. The long locks hanging over his usual sweatband and his signature grin are certainly worthy of a GQ cover, or at least Maxim, if he has to settle.

17. Dwyane Wade

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    It's no surprise that people are beginning to see a connection with hip-hop artists wanting to be athletes and athletes wanting to be hip-hop artists.

    Take Wade in this photo, for example. Aside from looking like the softest mob boss the world has ever known, he certainly looks like Lil' Jon without the dreads or Jay-Z with straight teeth.

16. Tony Parker

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    Parker was already a pretty boy long before he met Eva Longoria, and now that the two have split, don't expect him to change.

    The San Antonio Spur has spent time on the bench for injuries, and it also can appears as if he's faking a sprained ankle just so he can show off his new suit. Parker is actually French, if that helps to explain things.

15. Troy Polamalu

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    When you first think of Troy Polamalu, you might think of a tremendously talented safety that seems to be able to cover the entire defensive backfield. Most likely, though, you will think of his gigantic, loud hairstyle that even has its own insurance policy.

    Polamalu isn't your typical pretty boy, but believe you me, he deserves his place on the countdown.

14. Derek Jeter

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    Surprised to see Jeter outside the Top 10? I would be too. However, Jeter has sustained a level of pretty boy for so long, he's now getting passed by the newest members, which are taking the image to a whole new level.

    Still, Jeter is a Yankee, and a certain level of swag goes with the pinstripes, even in a quiet, confident manner.

13. Kobe Bryant

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    Does "WTF?" come to mind at first glance of these photos? Well, once the initial shock is over and your face stops matching the color of these outfits, we will continue.

    You good? Alright. Kobe actually thought this photo shoot was a good idea, but he hit the list as soon as he agreed to do his first photo shoot, years ago. Bryant is another prime example of swagger off the court, which normally is synonymous with "Pretty Boy."

12. Floyd Mayweather Jr

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    Floyd Mayweather Jr. is a sucker for the camera, never missing an opportunity to boost his rep. At least, that is, when TMZ doesn't get in the way and ruin his life. I'm, of course, only saying what he's probably thinking, denying that he is able to make responsible decisions.

    In the days of Don King, boxers didn't need to boost their own rep; that crazy-haired bastard did it for them. Since those days, boxers are more flamboyant than ever, and Mayweather Jr. is the ringleader.

11. LeBron James

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    This photo isn't hard to find when searching "LeBron James" in Google. It's not surprising, considering James isn't hard to find at other sporting events besides his own, donning giant diamond earrings that make his ears like my Great Uncle Harry's.

    Just kidding, I don't have a Great Uncle Harry.

10. Rafael Nadal

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    Rafael Nadal tops the list of current tennis player pretty boys. Taking a page from Federer's book, Nadal also has the long, dark locks and white headband. However, the added element of a foreign name and darker skin, oh and photo shoots that have nothing to do with tennis, and we have a winner.

9. Mark Sanchez

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    It took FOREVER to find a photo of Sanchez in which he wasn't wearing his Jets uniform, or a GQ logo in the bottom right. Sanchez has posed for several magazines, and it seems like he always has perfect hair despite wearing a helmet for four quarters. 

    Another USC product, Sanchez comes from a pedigree of pretty boys in the California sun.

8. Chad Ochocinco

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    We all know Chad by now. The ever-TV-present personality that likes to play football on the side. Ochocinco has certainly worn some crazy outfits before, but his level of pretty is beyond common comprehension, and even sometimes common sense.

    The Bengals wide receiver is so flamboyant that he has been approached by several networks for reality TV series, and he has thus far signed on to do two of them.

7. Tony Romo

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    Tony Romo caught a little of the pretty bug when he dated singer Jessica Simpson, and very publicly at that. Soon after, his clean-cut image began to garner the pretty boy tag, and it has stuck ever since. Romo is active in all kinds of sports, but it seems as soon at the cameras are on him, he's all swag.

6. Joey Harrington

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    When Joey Harrington first began getting NFL attention at the University of Oregon, he was also getting attention for being able to wear a suit and play concert piano simultaneously.

    Then, as he began doing national interviews for football and piano playing, gold diggers would follow. However, Harrington's career would fizzle, and the women would leave him and flock to Tom Brady and Tony Romo, only to find out they want to marry real women. Sad ending for gold diggers everywhere.

5. Terrell Owens

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    This shot of Terrell Owens crying over perceived media attacks on his quarterback, all while wearing diamond rocks on his ears and designer shades, solidified his image as a soft-hearted, easily-offended pretty boy. Owens has since gone on TV with good receiver buddy Chad Ochocinco to take his career to the next level.

    Maybe now that Owens is on TV, he will finally grasp "reality," but probably not.

4. Alex Rodriguez

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    You know when you see those people on American Idol, and you wonder where the people were to tell them they can't sing? This photo seems something like that, but then again, A-Fraud is getting paid big money to look even more rich.

    Owner of the largest sports contract in history, Alex Rodriguez show knows how much he's worth, and his clothing is probably worth more than I make in a year.

3. David Beckham

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    Beckham is an obvious choice, having participated in more photo shoots than he has games on a soccer field.

    His high-profile marriage to a Spice Girl and chosen profession make him a prime target for pretty-boy cameras. Add an underwear photo shoot, and Beckham is a prime suspect with the perfect recipe for pretty boyhood. 

2. Tom Brady

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    Who could top Ugg boots and long, flowing hair that resembles pop star Justin Bieber? There's only one person, and he is on the next slide.

    In the meantime, for all the fellas out there with dreams of marrying a supermodel, you might want to rethink things. Here is the "after" picture of what happens when you completely turn into the other side of the leash. However, I'm sure if you asked Tom, Gisele is totally worth looking like a fifth-grader on picture day.

    Hint: Brady is on the left in this photo.

1. Cristiano Ronaldo

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    When your exploits include reported threesomes with prostitutes in French hotel rooms, underwear shoots with super model co-stars, and a large soccer contract, you can top any contender on the list of pretty boys around the world.

    Ronaldo is the poster man for this countdown and happily replaces David Beckham as having entirely too much fame that has nothing to do with soccer. He's actually a very talented athlete when his tighty whities don't overshadow his play.

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