Yahoo Turns 25: Take a look back at some of the most popular athletes in the last 25 years in sports

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(Amber Matsumoto/Yahoo Sports)
(Amber Matsumoto/Yahoo Sports)

This story is part of a series to celebrate Yahoo’s 25th birthday. Thanks for joining us along this wild, wonderful ride.

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With Yahoo turning 25 years old, we’re taking a look at some of the most popular athletes of the era.

This isn’t a list of the most-liked athletes. Some are beloved. Some are divisive. Some are universally reviled. But they all demand your attention.

Here’s a look back at the athletes who have defined the last 25 years in sports.

LeBron James

LeBron James in 2011 with the Miami Heat. (Robert Duyos/Sun Sentinel/Tribune News Service via Getty Images)
LeBron James in 2011 with the Miami Heat. (Robert Duyos/Sun Sentinel/Tribune News Service via Getty Images)

Has there been a bigger athlete during the internet age than LeBron James? The first player to truly challenge Michael Jordan’s GOAT throne, James somehow exceeded the tremendous hype of his prep days to set new standards for how basketball is played and business is done in the NBA.

Tiger Woods

Tiger Woods at the 2019 Masters. (AP Photo/David J. Phillip,File)
Tiger Woods at the 2019 Masters. (AP Photo/David J. Phillip,File)

From his meteoric rise through his tabloid fall to his redemption at the 2019 Masters, few sports stories have personified the internet era better than Tiger Woods’. A transcendent athlete who broke down race barriers and changed the game, Woods is always compelling.

Serena Williams

Serena Williams after winning Wimbledon in 2016. (AP Photo/Ben Curtis)
Serena Williams after winning Wimbledon in 2016. (AP Photo/Ben Curtis)

Before Serena Williams burst onto the scene with her sister Venus, a black woman from Compton making waves in the tennis world was inconceivable. Now 21 years after winning her first grand slam, Serena has 23 and is widely considered the greatest women’s tennis player ever. Oh — and she won one of them while pregnant. The internet is on board with all of this.

Tom Brady

<a class="link rapid-noclick-resp" href="/nfl/teams/new-england/" data-ylk="slk:New England Patriots">New England Patriots</a> quarterback Tom Brady (AP Photo/Tim Sharp, File)
New England Patriots quarterback Tom Brady (AP Photo/Tim Sharp, File)

Tom Brady is inarguably the greatest championship quarterback of all time. But is he the the greatest quarterback ever? Throw in a few New England Patriots cheating scandals, and you’ve got a debate custom-made for the internet.

Michael Jordan

Michael Jordan (Tony Ranze/AFP via Getty Images)
Michael Jordan (Tony Ranze/AFP via Getty Images)

Michael Jordan’s peak with the Chicago Bulls arrived before the rise of the internet. It’s a testament to his unrivaled legacy that he’s maintained such a significant presence on the web post-retirement. Crying Jordan doesn’t hurt his cause.

Barry Bonds

Barry Bonds in 2002. (Photo by Jed Jacobsohn/Getty Images)
Barry Bonds in 2002. (Photo by Jed Jacobsohn/Getty Images)

With or without PEDs, Barry Bonds is arguably the greatest hitter baseball’s ever seen. That his legacy is tarnished as the face of MLB’s steroid era gave birth to one of the fiercest debates of the internet age. Does the most-feared hitter in baseball history belong in Cooperstown?

Usain Bolt

Usain Bolt at the 2016 Olympics in Rio. (Photo by William Volcov/Brazil Photo Press/LatinContent via Getty Images)
Usain Bolt at the 2016 Olympics in Rio. (Photo by William Volcov/Brazil Photo Press/LatinContent via Getty Images)

For three straight Olympics, one question prompted appointment viewing unlike than any other in sports. Is Usain Bolt the fastest man in the world? In Beijing, in London and in Rio, the answer was always a resounding yes. Blessed with bottomless swagger and the game to back it up, the greatest sprinter the world’s ever seen is also one of its greatest showmen.

Peyton Manning

Peyton Manning in the Super Bowl in 2007. (Photo by Gary W. Green/MCT/via Getty Images)
Peyton Manning in the Super Bowl in 2007. (Photo by Gary W. Green/MCT/via Getty Images)

Between his aww-shucks demeanor, self-deprecating humor and mastery of game tactics, Peyton Manning commanded the admiration and respect of the football world while winning two Super Bowl titles. By the time he was done, Tom Brady had surpassed him in the GOAT conversation thanks to his abundance of rings. But was he truly the better quarterback in his prime?

Brandi Chastain

Brandi Chastain's iconic World Cup moment in 1999. (Hector Mata/AFP via Getty Images)
Brandi Chastain's iconic World Cup moment in 1999. (Hector Mata/AFP via Getty Images)

Brandi Chastain wasn’t the best player on the historic 1999 USA World Cup team. That honor belongs to Mia Hamm. But as far as moments go, few in sports are bigger that Chastain’s game-winner to beat China in penalty kicks for the World Cup title. The image of Chastain in her sports bra emblazoned magazine covers and stands alongside USA Hockey’s “Miracle on Ice” as one of American sports’ proudest moments.

Alex Rodriguez

Alex Rodriguez with the New York Yankees. (Photo by Jim McIsaac/Getty Images)
Alex Rodriguez with the New York Yankees. (Photo by Jim McIsaac/Getty Images)

In 2014, Alex Rodriguez was suspended for an entire season, a baseball pariah at the center of MLB’s steroid scandal. Now he’s engaged to Jennifer Lopez and embraced by the game as baseball’s most prominent broadcaster. Will he make the Hall of Fame? It seems unlikely. But Barry Bonds should probably take some public relations cues regardless.

Kobe Bryant

Kobe Bryant (Photo by Lisa Blumenfeld/Getty Images)
Kobe Bryant (Photo by Lisa Blumenfeld/Getty Images)

Before his death in a helicopter crash alongside his 13-year-old daughter Gianna, Kobe Bryant was already an icon. A five-time champion and a fierce competitor whose intensity rivaled that of Michael Jordan, Bryant was proclaimed the greatest Los Angeles Laker by none other than Magic Johnson. His basketball legacy stands among the titans of the game while his death is one of the great tragedies in sports.

Lance Armstrong

Lance Armstrong (Photo by Bryn Lennon/Getty Images)
Lance Armstrong (Photo by Bryn Lennon/Getty Images)

Lance Armstrong made America care about cycling while winning the Tour de France seven times. He did so while acting as one of the world’s greatest cancer-awareness advocates. Then he devolved into one of sports’ greatest villains, an admitted (eventually) cheater who vilified anyone his path on his way down from the top. His is a story made for the internet. 

Colin Kaepernick

Colin Kaepernick, middle, kneeling with Eric Reid, right, and Eli Harold. (Michael Zagaris/San Francisco 49ers/Getty Images)
Colin Kaepernick, middle, kneeling with Eric Reid, right, and Eli Harold. (Michael Zagaris/San Francisco 49ers/Getty Images)

With the simple act of taking a knee, Colin Kaepernick elevated himself from quarterback to cultural force. Praised as a champion of racial equality and social justice, reviled by detractors who view his protests as unpatriotic, Kaepernick is arguably the most controversial athlete of his time.

Roger Federer and Rafael Nadal

Rafael Nadal and Roger Federer at the 2009 Australian Open. (AP Photo/Rick Stevens)
Rafael Nadal and Roger Federer at the 2009 Australian Open. (AP Photo/Rick Stevens)

Each of these icons’ stories easily stands alone. But they’re better told as one. The two greatest champions in men’s tennis history put on the most dominant run the sport’s ever seen for a decade. Then they did it again for five more years, all while delivering the game’s most thrilling matchups when the stakes were at their highest (and they’re still going strong). 

Michael Phelps

Michael Phelps at the 2016 Rio games. (Photo by Michael Kappeler/picture alliance via Getty Images)
Michael Phelps at the 2016 Rio games. (Photo by Michael Kappeler/picture alliance via Getty Images)

By the time Micheal Phelps donned his 28th Olympic medal in 2016, the sight had almost become blasé. The most decorated athlete in Olympic history by a long shot (Soviet gymnast Larisa Latynina comes in second with 18), Phelps dominated four Olympic games from Athens to Rio while compiling 23 golds. Detractors can point to the abundance of medals made available to swimmers all they want, but nobody comes close to Phelps’ tally.

Conor McGregor

Conor McGregor before his fight with Khabib Nurmagomedov in 2018. (AP Photo/John Locher, file)
Conor McGregor before his fight with Khabib Nurmagomedov in 2018. (AP Photo/John Locher, file)

Brash, savvy, vulgar, petulant and immensely talented, Conor McGregor is the fight game’s preeminent heel. He doesn’t care what you think about his attitude or his rap sheet, as long as you tune in. And tune in fans and haters alike do whenever McGregor is on the card. Even if it’s for a sham boxing match.

Simone Biles

Simone Biles at the Rio games in 2016. (Photo by Ian MacNicol/Getty Images)
Simone Biles at the Rio games in 2016. (Photo by Ian MacNicol/Getty Images)

Simone Biles arrived at the 2016 Olympics as the face of the “Final Five,” the USA women’s gymnastics team loaded with massive expectations. When she left Rio, she took with her five Olympic medals — four of them gold — including golds in team competition and as the all-around champion. After her anointment as the greatest gymnast in the history of the sport, Biles has somehow gotten even better with 2020 in Tokyo looming.

Shaquille O’Neal

Shaquille O'Neal after winning his second NBA championship and Finals MVP in 2001. (Stan Honda/AFP via Getty Images)
Shaquille O'Neal after winning his second NBA championship and Finals MVP in 2001. (Stan Honda/AFP via Getty Images)

Shaquille O’Neal joined the NBA as a physical force like basketball had never seen. A 7-1, 300-plus-pound giant who could run the floor and dominate the paint, O’Neal made an immediate impact as the 1993 Rookie of the Year averaging an astounding 23.4 points and 13.9 rebounds. Four championships and three Finals MVPs later, his outsized personality was the only serious competition to his throne as the most dominant big man of his era.

Tim Tebow

Former Florida quarterback Tim Tebow (AP Photo/Phil Sandlin)
Former Florida quarterback Tim Tebow (AP Photo/Phil Sandlin)

A college football legend and an NFL bust, Tebow has ridden his polarizing popularity to a shot in the New York Mets’ farm system as a 32-year-old. Love him or loath him, there’s no denying the impact he made in leading Florida to a pair of national championships. No matter where you come down on Tebow, odds are you’re paying attention to what he’s doing.

Sammy Sosa and Mark McGwire

Chicago Cubs slugger Sammy Sosa and St. Louis Cardinals slugger Mark McGwire (Christina Macias/Belleville News-Democrat/Tribune News Service via Getty Images) (Horiz)
Chicago Cubs slugger Sammy Sosa and St. Louis Cardinals slugger Mark McGwire (Christina Macias/Belleville News-Democrat/Tribune News Service via Getty Images) (Horiz)

In 1998, America was enthralled with baseball. Three years removed from a strike that drove fans away, Sammy Sosa and Mark McGwire engaged in a home run and MVP race brought them back in droves and made headlines beyond the sports pages. By the time suspicion of steroid use spilled over into the halls of Congress seven years later, a feel-great moment for the sport had devolved into one of its biggest black eyes.

Floyd Mayweather

Boxer Floyd Mayweather Jr. (AP Photo/Isaac Brekken)
Boxer Floyd Mayweather Jr. (AP Photo/Isaac Brekken)

Floyd Mayweather’s greatness is undeniable. His 50-0 mark stands as a bellwether for boxing, his precision and dedication to perfection in the ring unassailable. His problems outside the ring that include a multitude of domestic violence accusations are impossible to ignore.

Megan Rapinoe

Megan Rapinoe at the 2019 World Cup. (AP Photo/Francisco Seco, File)
Megan Rapinoe at the 2019 World Cup. (AP Photo/Francisco Seco, File)

Megan Rapinoe could make this list on her merit as a soccer player alone. The face of the 2019 World Cup champions, Rapinoe took home the Golden Ball and Golden Boot awards as the tournament’s best player and leading goal scorer. That she uses her platform to advocate for LGBTQ awareness, women’s rights and equality and social justice elevates her status beyond the field of play.

Stephen Curry

Stephen Curry, left, at the 2017 NBA Finals. (MediaNews Group/Bay Area News via Getty Images)
Stephen Curry, left, at the 2017 NBA Finals. (MediaNews Group/Bay Area News via Getty Images)

Stephen Curry joined the NBA in 2009 as an undersized scoring guard with a penchant for hitting big shots. Two league MVPs and three NBA championships later, he’s the standard-bearer for a basketball revolution. While other teams looked to emulate the success of the Golden State Warriors, encouraging shooters to shoot early, often and deep from 3-point range, none of those teams have Curry — or their success.

Dale Earnhardt

Dale Earnhardt after his long-awaited Daytona 500 victory in 1998. (AP Photo/Terry Renna)
Dale Earnhardt after his long-awaited Daytona 500 victory in 1998. (AP Photo/Terry Renna)

In 1998, Dale Earnhardt filled the one glaring gap in his illustrious NASCAR career, securing a long-awaited victory at the sport’s most prestigious event, the Daytona 500. Three years later, the track that eluded him for most of his career claimed his life. Earnhardt’s fatal crash at the 2001 Daytona 500 robbed the sport of its most beloved champion and sent shockwaves beyond the racing community.

Cristiano Ronaldo and Lionel Messi

Cristiano Ronaldo and Lionel Messi. (Photo by Pressefoto Ulmer\ullstein bild via Getty Images)
Cristiano Ronaldo and Lionel Messi. (Photo by Pressefoto Ulmer\ullstein bild via Getty Images)

Soccer icons and rivals on a global stage, Cristiano Ronaldo and Lionel Messi regularly ignite one of the hottest arguments in sports. Who’s the best player in the world? With their primes intersecting, their rivalry stands alongside the likes of Ali-Frazier, Magic-Bird and Federer-Nadal among the greatest in sports history.

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