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The 50 Coolest Athletes of All Time

Michael AkelsonJun 7, 2018

Back in February, GQ released its list of the 25 coolest athletes of all time

It came together pretty nicely, but we here at Bleacher Report simply weren't satisfied.

We wanted our own definitive list. So that's exactly what we made.

We found the 50 guys who just had more swagger than everybody else.  

Here are the 50 coolest athletes of all time. 

Honorable Mentions

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Here are four guys who just barely missed out on all the fun:

Terrell Owens: He's selfish, annoying and overdramatic. But you'd be lying if you said T.O wasn't cool.

Billy "White Shoes" Johnson: He wasn't cool for that long, but for about five years there was nobody as smooth as White Shoes. This man invented the touchdown celebration. 

DeSean Jackson: He's about two years away from making the top 50, but for now, DeSean simply hasn't been cool long enough to make the list.

Ozzie Smith: The Wizard of Oz played the field more gracefully than anybody else. He made diving plays routine, and he also hit one of the most iconic home runs in MLB history. The fact that he flipped out to his position in the field is just gravy.

50. Darryl Dawkins

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Nobody was more ferocious with a basketball in their hands than Darryl Dawkins.

Chocolate Thunder snapped backboards like they were rubber bands.

And then after he was done, he would name his dunks.

He wasn't a great NBA player by any means, in fact I wouldn't even say he was good, but boy could he throw it down.   

49. Manny Ramirez

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When Terrell Owens complained about his teammates, we said it was annoying. When Barry Bonds tossed his bat after a home run, we said it was cocky.

When Manny Ramirez did it, we said it was Manny being Manny.

He made phone calls during games, cut off throws even though he himself was an outfielder, high-fived fans and went into home run trots on balls that didn't even leave the park.

If anybody else did it, we'd hate them—but Manny was just so much damn fun to watch. 

His pine-tar glazed helmets and lazy demeanor are what we came to love about him.

Usually there's nothing cool about an athlete who doesn't go all out, but ManRam was the exception.

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48. Tony Hawk

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Nobody made skateboarding cooler than Tony Hawk.

For the better part of a decade he was the only reason we watched. 

Hawk shed the all-skaters-are-thug theory and became an idol for aspiring skaters everywhere.

He also made one of the most kick-ass video game series ever, which nobody would have ever even thought about buying if his name weren't attached.

I love Shaun White, but he isn't half the phenomenon Tony Hawk was.

No action sports star ever will be again.   

47. Lisa Leslie

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Lisa Leslie's impact on the WNBA was incredible.

She was the league's first star and the first woman to ever dunk during a game. If it weren't for her, there probably wouldn't even be a WNBA right now.

We can all laugh at the WNBA as much as we'd like, but nobody can say a bad thing about Lisa Leslie.

She was the game's first real icon, and she always showed that kind of swagger and confidence out on the court. 

46. Lawrence Taylor

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There was just one defender in the history of American Football who could win a game by himself. That man was Lawrence Taylor.

His presence on a football field alone was just as scary for fans to watch as it was for players.

What made him so scary was not only his unbelievable strength and speed, but also his crazy amounts of confidence and swagger.

He was really a guy who knew how to walk the walk.

45. Randy Moss

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When he entered the league in 1998, nobody really knew what to expect from Randy Moss. 

We all knew he was a physical freak with as much talent as any wide receiver to ever be drafted, but we also knew about his big-time attitude problems.

We got both.

Like a flash of lightning, Moss set the league on fire as a rookie in 1998 scoring 17 touchdowns to go along with 1,300 yards receiving. 

He started his career with Minnesota, grabbing an incredible 90 touchdowns in just six seasons.

Moss gained a reputation as one of the game's very best wideouts, but he also gained a reputation as one of the cockiest players to ever take the field.

And that's been the book on Randy Moss.

Questionable work ethic and questionable attitude. But with everything there is to dislike about Moss, there's no questioning his talent, and above all his swagger.  

44. Pete Maravich

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Pistol Pete Maravich was a wizard with the basketball.

The sweet-dribbling point guard could score like no other. Maravich averaged more than 40 points per game throughout his collegiate career at LSU.

He died at the age of 40 in 1998, and it was one of the saddest days in the history of sports.

43. Dominique Wilkins

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You don't get a nickname like "The Human Highlight Reel" without having some swagger.

And 'Nique had a ton of swagger. 

He could score from anywhere on the court, and he walked around with that strut in his step because of it.

42. Tiger Woods

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Think back to three years ago: If you could be one athlete, who would you be?

Probably Tiger Woods, right?

He had everything you could ever want. 

Tiger was a world icon, historically rich and the most successful active American athlete.

Yet he wasn't the least bit conceded, he always said the right things and he had a lovely family.

He was the model American, somebody we all wanted to be more like.

Three years ago he would have been in the top 10 for the sheer fact that he was so cool without even trying to be.

However, this isn't three years ago. An all-time scandal made him the envy of America no longer, but that doesn't omit what he was for so long.

Tiger will still always be remembered as one of the coolest athletes to ever live. 

41. Wayne Gretzky

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Sometimes somebody is just so good at something it makes them appear to be cooler than they really are.

Wayne Gretzky didn't dress cool, he didn't talk cool, he didn't even look cool. But he was.

Gretzky was so incredible at hockey that it made him cool against the most unlikely odds.

Nobody left a bigger mark on hockey than him.

40. Bobby Orr

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Speaking of guys who left a massive impact on hockey, I give you Bobby Orr.

He changed the way we thought about NHL defencemen and revolutionized the position.

And what's cooler than completely changing a position? 

39. Manny Pacquiao

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Manny Pacquiao does whatever he wants.

If he wants to fight in the middleweight class, he does it. If he wants to fight in the featherweight class, he does it.

If he wants to be in a movie, he does it. If he wants to run for office, he does it. If he wants to sing (badly albeit), he does it.

He's a modern renaissance man, and is there anything cooler than that?

38. Jim Brown

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Jim Brown was a man. 

He plowed through defenders for his entire nine-season career and dominated the game like no other football player ever had.

Then he retired and became the first-ever African-American action movie star, playing a key role in Academy Award-winner The Dirty Dozen, then starring in one of the first-ever interracial romance movies, 100 Rifles alongside Raquel Welch and Burt Reynolds.

Jim Brown was an innovator and a man who succeeded in all endeavors he pursued.

37. Chad Ochocinco

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Ever since he entered the league in 2001, no NFL player has entertained us more than Chad Ochocinco.

And you can call him selfish, you can call him arrogant, but you can't call him uncool. 

He ain't one of the most followed athletes on Twitter for nothing.

36. Wilt Chamberlain

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I could sit here and talk about the fact that Wilt Chamberlain once scored 100 points in a game or the fact that he averaged 27 rebounds per game as a rookie.

But I don't have to.

All I have to say is Wilt Chamberlain once claimed to have slept with more than 20,000 women—and people believed him.

That's an automatic bid onto this list.

35. Mario Andretti

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This guy was auto racing for a while. 

Formula One, IndyCar, NASCAR, he won at them all.

To this day he still remains as arguably the most famous auto-racer of all time.

34. Dwyane Wade

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Has any NBA player this side of Clyde Frazier shown more style?

Dwyane Wade is a NBA champion and one of the league's best players on the court; off of it, he embraces his star.

He always dresses the part and never says the wrong thing.

It speaks a lot to the type of person Wade is when you consider he plays for the dreaded Miami Heat, yet nobody seems to have a problem with him. 

33. Kobe Bryant

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Kobe Bryant doesn't care if you love him or hate him. He doesn't care if you think he's better than Jordan or not. He doesn't care if he scores 100 points or 15.

He only cares if he wins, and that's pretty damn cool. 

32. Michael Irvin

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Before there was T.O, Moss or Ochocinco, there was Michael Irvin.

In his day he was the ultimate diva wide receiver, and he knew how to back it up on the field.

Irvin made catching touchdowns cooler than everybody else for the simple fact that every time he caught one he was proving somebody wrong who thought his ego would get in the way of his game. 

31. Charles Barkley

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At 6'6", Charles Barkley was one of the shortest players to ever play power forward.

But he never let his size get in the way of his physicality. He averaged nearly 12 rebounds per game throughout his career by playing tough.

And he was just as tough with his mouth as he was with his body, never shying away from saying what was on his mind.

Even today in the announcer's booth, Barkley says whatever the hell he wants. 

30. Björn Borg

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He may not have been a great talker, but back in the 1970's, Björn Borg had as much style as anybody in sports.

His headband and long hair were every bit as deadly as his backhand. 

In fact, Borg was so cool, Luke Wilson tried to play a character based on him in The Royal Tenenbaums, and it got pretty ugly.

Somebody should have told him nobody could rock the headband-beard combo like Borg.

29. Mickey Mantle

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The MLB will never again see a player quite like the Mick.

He hit the ball harder than anybody else from either side of the plate. Mantle would play games hungover and hit two home runs.

It's a shame he was never able to get his personal life under control, he could have been the greatest of all time. 

28. Tom Brady

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Our biggest problem as a nation with Tom Brady is that he's too perfect. We hate him because he's so damn successful.

He's a three-time Super Bowl champion with a supermodel wife and two MVP awards. 

And our top argument as to why we hate him is because he has effeminate hair. 

Edge: Brady. 

27. Ray Lewis

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Ray Lewis is the most fiery competitor in the history of football.

His locker room speeches and pregame dances send chills down the spine.

He cares so much more about the game than anybody else in the league.

And there are few things cooler and more respectable than somebody who goes out there and never gives less than 110 percent.  

26. Dwayne "The Rock" Johnson

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Was he an athlete? That's questionable.

Was he cool? Absolutely.

Nobody ever did anything with more charisma than Dwayne Johnson.

Throughout his entire run with the WWE, Dwayne "The Rock" Johnson made audiences scream every time his face was on the screen.

He was the best character in the history of wrestling by a landslide.

Nobody has nor ever will be more comfortable than The Rock in front of a crowd.  

25. Roberto Clemente

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Roberto Clemente was a Hall of Fame baseball player by day and a humanitarian by night.

One of the first great Hispanic baseball players, Clemente was one of the nicest people to ever play the game.

He forever left an imprint on us all to be less selfish.   

24. Joe DiMaggio

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Joltin' Joe DiMaggio was a perennial All-Star on the field, with a 56-game hitting streak and three MVP awards to his credit; off it he dunked his donuts and bagged Marilyn Monroe. 

The Yankee Clipper was an absolute icon back in his heyday, constantly being referenced in art, movies, TV shows and literature. 

23. Reggie Jackson

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He played just five seasons in New York, yet Reggie Jackson is one of the most iconic Yankees of all time.

The man who once called himself "The Straw that Stirs the Drink" was cocky and hated upon first arrival in New York.

But he quickly shed that image, coming to be known as one of the coolest men in New York thanks in large part to a three-home run game in the World Series. 

22. Derek Jeter

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Derek Jeter is a more popular, more respected, more cool version of Tom Brady.

The fact that Jeter has played his entire career in New York, yet never had a bad word printed about him speaks to the type of person he is. 

He's a class act, and he could be the mayor of New York if he really wanted.

21. Joe Montana

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They didn't call him "Joe Cool" for nothin'.

Joe Montana was more graceful than everybody else under pressure. How else do you win four Super Bowls?

20. Julius Erving

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Dr. J was one of the greatest dunkers in NBA history.

He flew higher than everybody else and had some of the best moves in NBA history. 

His "Rock the Baby" dunk remains one of the coolest moves in the history of basketball.

19. Earl Monroe

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Speaking of NBA players who had some serious moves, I give you Earl Monroe.

Monroe had arguably the best dribbling moves of any player in NBA history.

On the playgrounds he was nicknamed "Black Magic," then "Black Jesus."

He and Walt Frazier combined for the Knicks to form one of the coolest backcourts in NBA history back in the early 1970's.

18. Barry Sanders

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Before every play Barry Sanders would look at the end zone and tell himself, "If I'm not standing there with the ball in my hand by the end of this play, I'm not doing my job."

And he firmly believed it.

He probably lost 500 yards in his career by running backwards, but he probably gained 5,000 the same way.

Sanders was one of the most explosive players in the history of sports and a complete joy to watch.

17. Bob Gibson

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Bob Gibson showed no sympathy out on the baseball diamond. He was never afraid to throw right at your cranium if he thought you were crowding his plate.

He was tough and talented, unsympathetic and scary.

Gibson also played for the Harlem Globetrotters, which definitely earns him some extra points. 

16. Rickey Henderson

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He hit more leadoff home runs than anybody else. He stole more bases than anybody else. He scored more runs than anybody else. And he talked in third person more than anybody else.

That was Rickey Henderson, every bit as cocky as he was talented. 

Yet we loved to hear him talk. 

His act simply never got tired, because he had the talent and swagger to back up what he said. 

15. Pele

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I don't like soccer in the least bit, but even I know it would be a crime to omit Pele from this list.

The coolest soccer player ever, plain and simple.

14. Arthur Ashe

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Plenty of guys hit the ball harder than Arthur Ashe. Plenty of guys had a better backhand than Ashe.

But nobody played the game with more grace.

And more importantly, nobody was a better man off the court.

We lost him far too early, but his impact on the Civil Rights movement will never be forgotten. 

13. Shaquille O'Neal

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Few sports stars ever became as much of a cultural icon as Shaq. 

He tried everything. He wanted to rap, he gave it a shot. He wanted to star in a movie, he did it.

Shaq stood for all that we loved in American athletes. He just had fun out there.

He really enjoyed playing basketball. Shaq embraced his fans, he embraced his nicknames, he embraced everything.

And there's something pretty cool about a guy who just has fun with life. 

12. Earvin "Magic" Johnson

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The day Magic Johnson announced he had been diagnosed with HIV remains one of the saddest days in sports history.

That's because he played the game so fast and smoothly. 

He ran the point for the Showtime Lakers, arguably the coolest team of all time, and he played point guard and center with success.

Basically, Magic could do anything on the basketball court. 

11. Allen Iverson

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You either loved Allen Iverson or hated him, there was no in between. 

And that's because not everybody was ready to accept how he was changing the league.

His cornrows and baggy clothes gave him a reputation as the bad guy, but he was really just bringing the NBA into the future.

Iverson took the NBA into its current era where dreadlocks and tattoos reign supreme.

He was arguably the fastest player in NBA history and the league's most explosive scorer as well.

AI threw his body all over the court despite his small frame, and he always gave 100 percent. He was a trendsetter and an all-time great, whether you like it or not. 

10. Willie Mays

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As far as I know, there's only been one player in the history of baseball who is a true five-tool player.

That man is Willie Mays.

One of the reasons why he excelled so much was the fact that he loved playing the game so much.

It was like watching a kid out there. He was always grinning from ear to ear, always hustling and making basket catches in the outfield.

He was a thrill to watch. 

9. Ken Griffey Jr.

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Speaking of guys who played the game like a kid, how 'bout Ken Griffey?

Back in the 1990's, Griffey and his backwards cap were the definition of cool.

The power hitting superstar patrolled the outfield as gracefully as anybody had since Willie Mays.

And how 'bout that swing? So, so, so pretty.

The thing that made Junior so cool was the fact that he never even wanted to be. He was so effortlessly cool, like he was just born that way.  

8. Bo Jackson

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Bo Jackson was a piece of art. 

An All-Star in two sports, Bo was just a pure athletic specimen. 

He broke through linebackers and cranked home runs into the upper decks.

But he knows. Bo knows.

He knows he's a once-in-a-generation athlete. And he knows that he's cool. 

7. Mike Tyson

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Mike Tyson was more dangerous during a pre-fight interview than most boxers were in the ring.

The dude was scary. 

For a short while he was the most popular athlete on the planet. He was on his way to becoming one of boxing's all-time greats.

And even though that never came to fruition, the fact that he was once the coolest athlete alive can't be denied.

He talked the talk and walked the walk. 

6. Joe Namath

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You can call Joe Namath overrated, but you can't say he wasn't cool.

His Super Bowl guarantee alone was cool and badass enough to land him on this list, but it's not the only reason why he's here.

Namath was one of the first to use his sports excellence to become a big-time celebrity.

He was so cool that we're even willing to let the whole Suzy Kolber fiasco go.

5. Evel Knievel

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Since we live in a world where being fearless is cool, Knievel is a shoo-in for this list.

4. Walt "Clyde" Frazier

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Back in the 1970's, Walt Frazier ran the point for the Knicks with precise passes and elite court vision. 

But it was his unique style off the court that really gained him notoriety.

Clyde was historically smooth and stylish.

And now as a Knicks announcer, he's only upped his coolness with his huge vocabulary and colorful suits. 

3. Deion Sanders

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Prime Time! Prime Time! Prime Time!

That's what we would all chant as we watched Deion Sanders return a punt all the way to paydirt.

He was built for the limelight.

Deion would bark at wide receivers just before he would pick off a pass intended for them, because that's who he was. He was a showman.

And when you put it all together and try to find one word to describe Deion Sanders, there's only one you can come up with: cool. 

2. Michael Jordan

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What can you say? Michael Jordan was an absolute killer.

Watching him play basketball was like watching a god; it's almost indescribable just how good he was.

His on-court swagger will never, ever be matched by anybody.

Just to get perspective of how awesome he was on the court, I like to watch the movie Space Jam sometimes. Not a great movie, obviously, but that final dunk scene just reminds me of how magical MJ really was.

1. Muhammad Ali

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I hate it when people say Muhammad Ali was a boxer—because he was so much more than that.

He was the biggest celebrity in the world for a while.

Ali was larger than life, an absolute superstar.

He was so cool that even the coolest, most charismatic leading man of our generation (Will Smith) couldn't muster up half the charisma of Ali while trying to play him in a movie.

Ali was named Sportsman of the Century by Sports Illustrated and Sports Personality of the Century by BBC.

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