50 Coolest Athletes in Sports History

Amber LeeSports Lists Lead WriterFebruary 9, 2012

50 Coolest Athletes in Sports History

0 of 57

    There is no shortage of coolness in professional sports, although some athletes seem to take fuller advantage of the life of splendor their career affords them than others. 

    Much like the career of a rock star or movie star, the money, the fame and the dames are all perks that come along with a successful career as a professional athlete.

    Most of the coolest athletes in history have been able to achieve professional greatness while balancing a social life that would make Mick Jagger envious. 

    Considering how many have failed at achieving that balance, it's obviously no small feat. 

    Here are the 50 coolest athletes from (almost) every sport. 

NHL's Coolest Ever

1 of 57

    If someone asked you to make a list of cool athletes, it probably wouldn't contain many (if any) hockey players. The talent in today's multicultural NHL is top notch, but the league is almost entirely devoid of recognizable characters. 

    Almost, but not entirely. Plus, the NHL was once a more flamboyant league and there's a wealth of retired players who are remembered as much for their colorful personalities as they are for their skills on the ice. 

5. Alexander Ovechkin

2 of 57

    Along with Pittsburgh Penguins forward Sidney Crosby, the Capitals' seemingly always slumping superstar Alexander Ovechkin is the most recognizable player in the game.

    If Ovi is popular in America, then he's a straight-up rock star in his native Russia. Or should I say rap star? Not only is Ovechkin the most eligible bachelor in the country, but apparently he has a direct line to Russian overlord Vladimir Putin. 

4. Gordie Howe

3 of 57

    Detroit Red Wings legend Gordie Howe left home at 16 to play hockey professionally, and within years he was one of the biggest stars in the game. Suppose they don't call him "Mr. Hockey" for nothing. 

    Not only is Howe's popularity amongst hockey fans enduring, but references to him in The Simpsons and Ferris Bueller's Day Off have forever immortalized him in pop culture history. 

3. Wayne Gretzky and Mark Messier

4 of 57

    Edmonton Oilers greats Wayne Gretzky and Mark Messier absolutely owned the 1980s. The two of them were together for one of the most successful spans of a franchise in sports history—bringing the Stanley Cup home to Edmonton an epic four times.  

    "The Great One" and "The Messiah" were the unofficial kings of Canada then, and are still two of the most beloved players to ever lace up skates. 

2. Henrik Lundqvist

5 of 57

    New York Rangers goaltender Henrik Lundqvist embodies all of the characteristics teammate Sean Avery is trying emulate—he's handsome, stylish, adored and effortlessly cool. 

1. Derek Sanderson

6 of 57

    In the late '60s/early '70s, retired Boston Bruins forward Derek "Turk" Sanderson was Boston's answer to "Broadway Joe" Namath.

    Sanderson was once named as one of the sexiest men in America by Cosmopolitan magazine, and his penchant for being photographed with beautiful women on his arm made him a gossip-column favorite. 

    Sanderson was a fan favorite and his flashy lifestyle attracted a lot of attention—he drove a silver Rolls Royce, rocked diamond rings and donned a mink coat. 

Tennis' Coolest Ever

7 of 57

    Tennis isn't the most exciting game in the world, but it has sure attracted its share of cool characters over the years—particularly in the 1980s. 

    Today, the talent in tennis might be every bit as good as it ever has been, if not better—but personality and style are lacking. 

5. Rafael Nadal

8 of 57

    Rafael Nadal is about as close to a rock star as you'll find in the game today. At just 25 years old, Nadal has already racked up 10 Grand Slam singles titles and is one of the best the game has ever seen. 

    Nadal is successful, he's passionate, he's captivating, he's got model-good looks and is rarely seen without a beautiful woman at his side. Every woman wants him; every man wants to be him. 

4. Andre Agassi

9 of 57

    In case you couldn't tell—Andre Agassi started making a name for himself in the late '80s. That flowing bleached-blond mullet might as well be a timestamp. 

    With eight Grand Slam titles, Agassi was one of the most successful players of the '90s.

    His luscious locks and aggressive style also made him a sex symbol—before settling down with Steffi Graf, Agassi was linked to living legend Barbara Streisand, model Brooke Shields and porn star Jeanna Fine. 

3. Bjorn Borg

10 of 57

    Despite a relatively brief career, Sweden's Bjorn Borg is widely regarded as one of the greatest players of all time. Borg's unprecedented success—winning 11 of the 27 Grand Slam tournaments he entered—made him one of the game's first superstars. 

    Borg has had high-profile romances—he was briefly married to Italian singer Loredana Berte and fathered a child with Swedish model Janike Bjorling.

    Today, Borg owns a successful fashion label that is second only to Calvin Klein in Sweden. 

2. Arthur Ashe

11 of 57

    Arthur Ashe was born in the very segregated South in 1943, and went on to have a barrier-breaking career. 

    Ashe was the first black player ever selected to the United States Davis Cup team and the only black man to ever with the singles title at Wimbledon, the US Open and Australian Open. 

    Ashe became an active leader in the civil rights movement and his tireless support of various social causes is remembered today—almost two decades after his death.

1. John McEnroe

12 of 57

    Hotheaded and controversial, John McEnroe was one of tennis' original bad boys and his seven Grand Slam titles make him one of the best to ever play the game. 

    McEnroe's larger-than-life persona is why is still one of the most recognizable faces in the sport, and in the last few years alone he's appeared on 30 Rock, Saturday Night Live, Curb Your Enthusiasm and CSI: NY. 


MLB's Coolest Ever

13 of 57

    Despite being known as America's pastime, Major League Baseball sure doesn't attract the coolest cast of characters. Doesn't it seem like there are a lot more crazy players than cool ones? 

    That being said, the sport isn't entirely lacking players with swag—let's take a look at the top five. 

5. Ken Griffey Jr.

14 of 57

    Ken Griffey Jr. is one of the most popular and prolific players in baseball history. In his prime he was considered, hands down, the best player in the game. 

    Griffey's career in the majors spanned over 20 years, and during that time he had lucrative endorsement deals with companies like Nike and Nintendo. 

4. Joe DiMaggio

15 of 57

    Just to look at him, you'd never guess that New York Yankees legend Joe DiMaggio had all that game—but, of course, he does. 

    DiMaggio was elected to the baseball Hall of Fame in 1955 and his 56-game hitting streak record still stands today.

    Must have been his prowess on the baseball field that gave him the confidence required to land actress Marilyn Monroe, the preeminent sex symbol of the 20th century. 

3. Brian Wilson and Tim Lincecum

16 of 57

    The coolness of San Francisco Giants pitching bro-tandem of Tim Lincecum and Brian Wilson is unrivaled in MLB.

    Lincecum's free-spirited-hipster-hippie persona combined with Wilson's unhinged frat-boy-turned-hipster persona is a potent mix of awesome. 

2. Bob Gibson

17 of 57

    Retired pitcher Bob "Hoot" Gibson's career in the majors was epic—two Cy Young Awards, one NL MVP and two World Series victories are just a few of the highlights. He was elected to the Hall of Fame in his first year of eligibility. 

    Gibson was one of the fiercest competitors the game has ever seen and was an intimidating presence on the mound.

    In 1981, New York Mets manager Joe Torre hired Gibson to serve as a sort of "attitude coach," hoping his killer instinct could be learned. 

1. Derek Jeter

18 of 57

    Derek Jeter has been the face of the New York Yankees, baseball's most storied franchise, for the better part of two decades. Jeter is already a legend and the undisputed King of New York (which isn't an official title just yet). 

    Jeter has got the looks, the style, the swag and enough skrilla in the bank to make him the envy of every man in America. Well, that and the fact that he beds enough broads to have a trademarked walk-of-shame routine suave enough to make national news. 

    Seriously, who else but Derek-freaking-Jeter could get away with sending a woman home with a gift basket of Derek Jeter memorabilia and come out looking like a hero?

Miscellaneous Sports' Coolest Ever

19 of 57

    "Miscellaneous Sports" might sound like a bit of a cop-out, but a catch-all category was required to highlight these cool customers. 

10. Shaun White

20 of 57

    Two-time Olympic gold medalist Shaun White is the cock of the walk in extreme snow sports. White has more confidence and gets more girls than any lanky dude with long red hair in history. 

9. Mark Spitz

21 of 57

    Michael Phelps may have surpassed Mark Spitz as the greatest American swimmer of all time, but he's got a long way to go if he ever wants to surpass Spitz's awesomeness.

    It takes one helluva of a man to pair that mustache with an American-flag Speedo and look cool as hell in the process. 

8. Usain Bolt

22 of 57

    Jamaican sprinter Usain "Lightning" Bolt is a three-time Olympic gold medalist and, on his best days, the fastest man in the world. But you don't have to tell him that—his legendary celebratory showboating suggests he already knows. 

    Bolt has embraced the global celebrity his success has provided him and looks as natural on the red carpet in a tuxedo as he does on the track. 

7. Tony Alva, Stacy Peralta and Jay Adams

23 of 57

    Tony Alva, Stacy Peralta and Jay Adams were all members of Santa Monica skate team the Z-Boys in the early '70s. The group is credited for the birth of vertical skating—they first started skating in drained pools during a severe summer drought in the mid-'70s. 

    Stacy Peralta wrote the screenplay for Lords of Dogtownthe 2005 movie starring Heath Ledger was based on their lives. 

6. Kelly Slater

24 of 57

    American surfer Kelly Slater is one of the most successful surfers in history—he's been crowed the ASP world champion 11 times and was the youngest and oldest to ever capture the title. 

    Slater's good looks and laid-back lifestyle have proven irresistible to some of the world's most beautiful women—Slater has been linked to Pamela Anderson, supermodel Gisele Bundchen and actress Cameron Diaz. 

5. Tiger Woods

25 of 57

    In the years since the epic sex scandal made headlines, there's no question that Tiger Woods has lost a little of his magic. Thankfully he had plenty of magic to spare, because he's still the coolest dude in the history of the game. 

    Actually, the fact that he managed to juggle dozens of women on the sly for years without getting caught is an epic accomplishment in itself. Hopefully Tiger is getting his mojo back on the course, because golf is just better when he's better. 

4. Mario Andretti

26 of 57

    Retired racing legend Mario Andretti's career spanned an amazing three decades and today his name is synonymous with the sport. 

    Andretti is one of the most successful American drivers in history and one of only two drivers to win races in Formula One, IndyCar, World Sportscar Championship and NASCAR. 

3. Bruce Lee

27 of 57

    Despite dying tragically young, Bruce Lee is, quite simply, a legend. Lee was an actor, director, producer, screen writer and founder of the Jeet Kune Do martial arts movement.

    He's a cultural icon and the most influential martial artist of all time. Seriously—just look at him—has anyone ever looked that cool in a leisure suit? 

2. Evel Knievel

28 of 57

    Legendary American daredevil Evel Knievel worked hard and played hard and it's an absolute miracle that he lived to see the ripe old age of 69. 

    During his stunt-performing career, Knievel suffered 433 broken bones—earning him an entry in the Guinness Book of World Records as the survivor of the "most bones broken in a lifetime." 

    At the height of his popularity, Knievel's motorcycle jumps were four of the 20 most-watched events on ABC's Wide World of Sports, and actor George Hamilton starred as the daredevil in a movie about his life. 

1. Muhammad Ali

29 of 57

    Muhammad Ali's boxing prowess made him a legend, and his often-replicated, never-duplicated, over-the-top persona made him a cultural icon. 

    The ultimate showman, Ali wasn't just content to beat his opponent in the ring—he lived for the pre-match circus. Ali's unfiltered, but often shockingly eloquent, trash talk made him one of the most popular athletes in the world.

NBA's Coolest Ever

30 of 57

    The NBA might have the coolest cast of characters in the history of professional sports.

    Unlike the NFL, the NBA operates under the idea that the league works best when superstar players are concentrated in large-market franchises—giving them the largest stage possible, thereby drawing in fans who like the drama. 

    This whole scenario isn't ideal for fans of small-market franchises, but it sure works for me!

10. John Wall

31 of 57

    Washington Wizards point guard John Wall was a superstar at the University of Kentucky, and became an instant sensation when he did the Dougie during his introduction at his first game in Washington in November 2010. 

9. Magic Johnson

32 of 57

    Magic Johnson is widely regarded as the greatest Los Angeles Laker ever—no small feat considering the company he's in. 

    His NBA career was epic. His rivalry with the great Larry Bird was legendary. And his post-NBA life as an HIV/AIDS advocate, entrepreneur, philanthropist, broadcaster and motivational speaker is nothing short of remarkable. 

    Magic has done it all, and judging by this photo, may have very well been the original hipster. 

8. Blake Griffin

33 of 57

    Los Angeles Clippers forward Blake Griffin was the breakout star of the 2011 NBA season—he won the NBA Slam Dunk Contest at the All-Star Game and was named the NBA Rookie of the Year. Sports Illustrated even ranked him as one of the NBA's 15 Greatest Rookies of All Time.

    Griffin's presence has transformed the Clippers—until recently, a total laughingstock—into a viable contender and preferred destination for big-name talent like Chris Paul and (according to SheridanHoops.com) Dwight Howard. 

    Oh, and how about that dunk on Oklahoma City Thunder center Kendrick Perkins? 

7. Allen Iverson

34 of 57

    It's a shame that Allen Iverson's issues—of which there are many—ended his NBA career prematurely because he was one of the most gifted and dynamic players in the league for over a decade. 

    Iverson never seemed to overcome the personal demons that lingered from a tough childhood in Newport News, Virginia, but his rebellious, hip-hop style made him a star in the league. 

    And it's thanks to him that we'll never think about practice the same way again. We talkin' 'bout practice, man!

6. Larry Bird

35 of 57

    Boston Celtics legend Larry Bird was the centerpiece of the NBA's original "Big Three," and one of the most prolific players the game has ever seen.

    Bird's aggressive on-the-court style and intense rivalry with Los Angeles Lakers superstar Magic Johnson were a stark contrast to his relatively unassuming look. 

    Bird has long since retired, but he's still very much relevant in today's NBA. He's currently the Indiana Pacers president of basketball operations and recently made headlines when he said he'd rather play with an aged Kobe Bryant for a championship than a younger, more talented LeBron James. 

5. Kobe Bryant

36 of 57

    Los Angeles Lakers guard Kobe Bryant has five championships in his NBA career, and if he hasn't already surpassed Magic Johnson as the greatest Laker of all time, a sixth championship should push him over the edge. 

    Kobe entered the league straight from high school, but even as a teenager he had the cool confidence to go toe to toe with (then) Lakers star Shaquille O'Neal. 

    Black Mamba is, without a doubt, one of the most polarizing players in the game—but he's impervious to the drama that the mere mention of his name tends to create. 

4. Michael Jordan

37 of 57

    The unflappable Michael Jordan is (almost) universally considered the greatest basketball player of all time. People who disagree are just desperate for attention.

    There's no need to discuss his resume; MJ's six NBA championships—and all that jewelry—tell the story for him. 

3. Wilt Chamberlain

38 of 57

    The late, great Wilt Chamberlain is one of the greatest and most dominant players the game has ever seen. He got his start playing for the famed Harlem Globetrotters before transitioning to the NBA in 1959. 

    Chamberlain owns a number of league records, but he is most famous for being the only NBA player in history to score 100 points in a single game. 

    Well, that and his notorious claim that he bedded over 20,000 women in his lifetime. Honestly not sure which is more impressive.

2. Julius Erving

39 of 57

    The Philadelphia 76ers legendary forward Julius "Dr. J" Erving is the fifth-highest scorer in NBA/ABA history and his revolutionary above-the-rim style of play forever changed the game for the better. 

    Erving is considered one of the best dunkers of all time and his signature "slam" dunk helped define his legacy and his legend. Well, that and his quintessential '70s style—never has an afro and a gold medallion looked so incredibly baller. 

1. Walt 'Clyde' Frazier

40 of 57

    Walt "Clyde" Frazier was the Hall of Fame point guard for the New York Knicks' two championship seasons in the early '70s. 

    Frazier is remembered as much for his smooth-stylin', off-the-court persona (said to be the inspiration for characters like Shaft) as his Hall of Fame career with the Knicks. 

Soccer's Coolest Ever

41 of 57

    We all are well aware that soccer isn't nearly as popular in America as it is in the rest of the world—which is a shame, because the passion that surrounds the game provides for some interesting storylines and a whole lot of drama.

5. Cristiano Ronaldo

42 of 57

    Real Madrid's superstar striker Cristiano Ronaldo might not be the kind of guy you want to have a drink with, but there's no denying that he's one of the most recognizable athletes on the planet and a straight-up rock star in his own right. 

    He is a prolific scorer—and not just in soccer. English actress Gemma Atkinson, American socialites Paris Hilton and Kim Kardashian, and Sports Illustrated Swimsuit Edition cover model Irina Shayk are just a few of Ronaldo's many conquests. 

4. Diego Maradona

43 of 57

    Retired Argentine footballer Diego Maradona is considered by many to be the greatest player of all time—surpassing the great Pelé. 

    Maradona has seen his share of controversy throughout his career—he incurred a 15-month suspension for testing positive for banned drugs in 1991 and was sent home from the World Cup for testing positive for ephedrine in 1994. 

    His stellar play may have made him rich and famous, but Maradona's positively Ozzie Guillen-like way with the media and various authority figures has made him a legend. 

3. George Best

44 of 57

    The Irish Football Association has called the late George Best, "the greatest player to ever pull on the green shirt of Northern Ireland." Best's talent got him discovered at the age of 15, but it was his personality and charisma that made him one of the first celebrity footballers. 

    Best enjoyed a life of excess and once said of his career, "I spent 90 percent of my money on women, drinks and faster cars. Then I wasted the rest." 

    Best married and divorced two models and fathered a son (actor Calum Best) before his hard living caught up to him—he died from complications three years after receiving a liver transplant. 

2. Pelé

45 of 57

    Retired Brazilian footballer Pelé is always, at the very least, in the discussion of the best players of all time. He's a national hero in his native Brazil and has been called "The King of Football." 

    After his retirement, Pelé had a few high-profile romances and acted in the occasional movie. Today Pelé is still in the spotlight, best known for his humanitarian work and his unofficial work as the global face of the sport. 

1. David Beckham

46 of 57

    At 36 years old, it's no secret that David Beckham's skills are on the decline—and have been for a while. His celebrity and bankability, on the other hand, have not suffered the same decline. 

    Beckham's athletic prowess and model-good looks are a powerful combination, and for a while he was the world's highest-paid footballer and one of the most desired men on the planet. 

NFL's Coolest Ever

47 of 57

    Despite being far and away the most popular sport in America, the NFL doesn't produce nearly as many fascinating characters as you'd assume it would.

    Of course, there are at least few cool customers that come to mind. 

10. Michael Irvin

48 of 57

    Michael Irvin, who gave himself the nickname "The Playmaker," might be the original diva receiver.

    Irvin is a born showman with exactly the kind of personality you'd expect from a player who came out of the University of Miami in the late '80s and went to play for the Dallas Cowboys for the entirety of the '90s. 

9. Clay Matthews

49 of 57

    Standing out on a team with Super Bowl MVP quarterback Aaron Rodgers is tough to do, but Green Bay Packers outside linebacker Clay Matthews manages to do just that. 

    Matthews' big hits, bigger personality and long, blond locks have made him one of the most popular players in the NFL today. 

8. Lawrence Taylor

50 of 57

    Recent personal tribulations aside, retired New York Giants linebacker Lawrence Taylor made a name for himself with his Hall of Fame career on the field, and his hard-partying lifestyle off the field.

    Taylor is one of the most memorable players in the history of the game. 

7. Cam Newton

51 of 57

    Just one year into his NFL career, Carolina Panthers quarterback Cam Newton is already one of the most buzzed-about players in the game.

    Nobody was sure what to make of the Heisman-winning QB out of Auburn when he came out of nowhere to lead the Tigers to a national championship. 

    Now we're sure. 

    Newton's style and charisma, combined with his exceptional physical talents, have made him a superstar after just one season in the league. 

6. Joe Montana

52 of 57

    With four Super Bowl victories highlighting his resume, retired San Francisco 49ers legend Joe Montana is tied with the Pittsburgh Steelers' Terry Bradshaw for the most championships won by a quarterback ever. 

    He is remembered for his intensity and unwavering calm, even in the most pressure-packed circumstances. They don't call him "Joe Cool" for nothing. 

5. Bo Jackson

53 of 57

    Remember when Michael Jordan decided to give up basketball to pursue a career in baseball and it was an epic failure? Well, MJ was probably inspired to follow his dreams thanks to the success of Bo Jackson. 

    After a successful Heisman-winning career at Auburn, Jackson was selected first overall in the draft by the Tampa Bay Buccaneers but opted to play baseball when the Bucs made him choose between the two. Eventually Jackson went on to split his time between the two sports, playing three seasons for the Oakland Raiders and six seasons in MLB. 

    Jackson was the first athlete to be named an All-Star in two major American sports and is still remembered for the popular "Bo Knows" Nike campaign. 

4. Deion Sanders

54 of 57

    Deion "Prime Time" Sanders is one of the most talented and versatile athletes ever, and is probably best known for his colorful stint with the Dallas Cowboys in the late '90s.

    Sanders primarily played cornerback in the NFL, but he also was known to play running back, wide receiver and kick/punt returner on occasion. Prime Time also clocked a few seasons in MLB—playing for the New York Yankees, Atlanta Braves, Cincinnati Reds and San Francisco Giants between 1989 and 2001. 

    Flashy suits and shiny jewelry helped "Neon Deion" land countless endorsement deals—and ultimately convinced Sanders that the world was eager for him to release a rap album (it wasn't). 

3. Kenny "The Snake" Stabler

55 of 57

    Kenny "The Snake" Stabler is the second-most famous quarterback to play for the legendary head coach Paul "Bear" Bryant at the University of Alabama. In his first year at Alabama, he played backup to the first—"Broadway Joe" Namath.

    Stabler was drafted by the Oakland Raiders in the second round of the 1968 NFL draft and was their quarterback in a playoff game against the Pittsburgh Steelers that is best remembered for The Immaculate Reception.

    His career in the NFL started off very promisingly, but was ultimately marred by injury. 

    Like his Alabama predecessor, Stabler's love of the nightlife and affinity for the fairer sex is well-documented—he has married (and divorced) three times. 

2. Jim Brown

56 of 57

    If you've ever looked at Cleveland Browns fans and wondered how they maintain their intensity and devotion despite decades of futility—the answer is Jim Brown. 

    Hall of Fame running back Jim Brown was drafted by the Browns in 1957, and he retired a Brown in 1965. Brown isn't just (arguably) the best football player of all time, he's also considered one of the greatest all-around athletes the U.S. has ever produced. 

    At Syracuse, Brown was a football standout, but also played basketball, lacrosse and ran track. After his NFL retirement, Brown went on to forge a successful acting career. 

    If you think about it, Brown isn't just one of the best athletes the U.S. has ever produced—he's actually one of the greatest Americans ever.

    For real. 

1. Joe Namath

57 of 57

    In terms of "coolness" in professional sports, the discussion begins and ends with legendary New York Jets quarterback "Broadway Joe" Namath.

    The indescribably talented athlete from Western Pennsylvania was never afraid to go against the grain—how else can you explain a Yankee outsider playing quarterback for Bear Bryant at the University of Alabama in the early '60s?

    When Namath was drafted by the Jets first overall, he had a agent negotiate the most lucrative contract in football history and went on to lead the Jets to their first (and only) Super Bowl championship in franchise history. 

    Namath enjoyed the fame and fortune he found in New York and was romantically linked with some of the most beautiful women in the world (including Raquel Welch), before eventually settling down. 

    A career plagued with injuries prevented the world from witnessing the full potential of an athlete who was one of the greatest raw talents in sports history.