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Looking Back at 20 Men Who’ve Defined the Past 20 Years

August 01, 2019DMT.NEWS

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Most Inspirational Men of the Last 20 Years

From 2006 to 2013, AskMen produced a yearly feature called the Top 49. The site’s editors at the time ranked the most successful and impressive men of the year, blending their opinions with reader votes to give a picture of what (and who) was the acme of masculinity right about then. 

RELATED: AskMen Through the Years

The men were invariably famous, encapsulating a who’s who of the guys dominating their respective fields, making headlines, capturing the zeitgeist and possibly even shifting the culture. Topping those lists were a movie star, a politician, an advertising mogul, two tech billionaires, a TV talk show host, a jet-setting spy and a pro athlete. One of them was dead — and two of them were fictional characters. 

While 2014 to 2016 saw slightly altered versions of the list that tweaked the format slightly, no official top men lists of any kind have graced the site’s pages since then.

But in celebration of 20 years of AskMen, we want to revisit the men who topped those lists — as well as the men who might have topped them from 1999 to 2005, and from 2016 to the present. 

So without further ado, here are the 20 men who’ve defined the past 20 years: 

1999: Neo

What We Might Have Written at the Time: “There are movies, and then there are movies. ‘The Matrix’ blew more or less everyone on Earth’s mind this year, and a big part of that is Keanu Reeves’ performance as Neo. The man we meet as Thomas Anderson could be any of us — a boring schlub who sits at a computer desk all day long, profoundly unhappy but without a clue why. Watching him come out of his shell (literally) and transform into The One — the black-leather-clad, kung-fu-fighting, bullet-dodging Alpha Male we all wish we were — was inspirational.”

Does It Hold Up? Thanks to the manosphere, the concept of the red pill that Neo takes in the film remains as culturally relevant as ever. The notion that technology has woven us all into a state of placid slumber is pretty on point; the Earth becoming scorched and unlivable is looking increasingly realistic, and damn if the most-tweeted-about male celebrity of 2019 isn’t Keanu Reeves himself, having a career resurgence. 

2000: George Bush

What We Might Have Written at the Time: “America is a land of opportunity, where anyone can rise from poverty to become a somebody. But it definitely doesn’t hurt, when attempting to fulfill your dreams, if your dad is the president. That being said, George W. — or ‘Dubya,’ as they call him — just made history. On top of winning one of the tightest presidential races of all time and becoming the first son of an American resident to himself be elected president, his down-home cowboy charisma makes him the sort of president you’d want to grab a beer with. This signals the dawn of a new era of American politics.”

Does It Hold Up? Not remotely.  

2001: Tiger Woods

What We Might Have Written at the Time: “Rowr! If you look up ‘dominant’ in the dictionary, you’re likely to find a picture of Tiger Woods these days. The man’s pursuit of golf glory has not only made him the most recognizable and financially successful player in the sport, it’s also leant a much-needed relevance to a sport seen by many as the domain of stuffy, old white guys. Every athlete declines at some point, but given how relatively non-taxing golf is on the body compared to football or basketball, Tiger’s machine-like dexterity and laser-focus could have him wiping the 18th hole with his competitors for years to come.”

Does It Hold Up? After several years of all-out dominance, Woods spent several years not accomplishing much on the green — and becoming a tabloid fiasco off it, with cheating allegations leading to some incredibly awkward leaked sexts, and hosts of dropped sponsorships. Sorry, Tiger. 

2002: Bill Gates

Bill GatesGettyImages

What We Might Have Written at the Time: “Bill Gates has been the richest man on the planet for several years now. Honestly, that sentence alone could make him worth of the top spot on any list of men, but this year he’s improved his stature, in our eyes at least, thanks to his winning the prestigious Jefferson Award (alongside his wife, Melinda) for ‘Greatest Public Service Benefiting the Disadvantaged.’ Giving back to those less fortunate is one of the greatest marks of a successful man; it’s what differentiates a rich crook hoarding his wealth from a jobs creator and a pillar of the community. Good on you, Bill.” 

Does It Hold Up? Mostly! Gates has remained one of the world’s richest men, but he’s also remained one of the world’s most charitable men. In a world where fellow tech billionaires Mark Zuckerberg, Elon Musk and Jeff Bezos have been dogged by controversy, it’s all the more impressive that Gates was a tech billionaire who never really pissed anyone off. 

2003: Orlando Bloom

What We Might Have Written at the Time: “Yes, he has pretty-boy good looks, flowing golden locks — well, at least in the movies — and he looks like you could probably take him in a bar fight. But Orlando Bloom is undeniably on top of the world right now. Starring roles in two of the year’s biggest movies good enough for you? Oh, perhaps you hadn’t heard of two little pieces of cinema called ‘Pirates of the Caribbean: The Curse of the Black Pearl’ and ‘The Lord of the Rings: The Return of the King.’ That’s fine! Bloom doesn’t mind ... he’s too busy dating Kate Bosworth. Big things are in store for this one.”

Does It Hold Up? The bloom has turned into a mild wilt for Bloom, if you will. Sure, he hasn’t been accused of anything horrible, and he was married to Miranda Kerr there for a while, but he hasn’t really done anything noteworthy outside of the LotR and PotC franchises — as Earth-shatteringly financially successful as they were — unless you count reprising his role as Legolas in the “Hobbit” movies (you shouldn’t). 

2004: Tom Brady

What We Might Have Written at the Time: “Tom Brady collects Super Bowl rings the way some people collect parking tickets. After passing for 354 yards in this year’s concluding contest, Brady locked down his second Super Bowl title in three years. The rest of the NFL is quivering. Sure, he has a good team around him, but Brady (who also snagged Super Bowl MVP) is the real deal. Elite vision, power arm, able to dodge seemingly any tackle — what more could you possibly ask for in a quarterback? Brady’s so good at football it might be time for him to pull a mid-’90s Michael Jordan and retire to play baseball for a while so some other teams can have a crack at the championship — at least for a few seasons.”

Does It Hold Up? Brady’s spent the past decade and a half adding to his prodigious trophy case; he and the Pats are now easily the most hated NFL team in the league … or possibly in history. That being said, depending on your political stance, his habit of leaving a “Make America Great Again” hat in the locker room might have you feeling a certain way about Mr. Gisele Bundchen. 

2005: Christian Bale 

Christian Bale GettyImages

What We Might Have Written at the Time: “Hollywood is as much a maze of shifting sands as it is a place — one moment you’re up, the next you’re down. The golden glory of success can quickly become the iron shackles of being typecast. But when you’re as talented as Christian Bale, the only constant is mind-blowing performances. A year after ‘The Machinist,’ which featured him wasting away into a near stick-figure to play a paranoid insomniac, he grabbed 2005 by the reins, delivering a powerfully real performance as John Smith in infamously strange art-house director Terrence Malick’s Pocahontas story, ‘The New World’ alongside what could only be described at the polar opposite of that film: the titular role in the gritty Batman reboot, ‘Batman Begins.’ Is there anything Bale can’t do?”

Does It Hold Up? After two more sequels, Bale’s done playing the Bat, but his star continues to shine brightly, picking up four Oscar nominations (including one win) since 2011, and apart from a certain viral video of him having a meltdown on set in 2009, has largely avoided real-life controversy. 

OK, now for some actual winners...

RELATED: An Interview With AskMen's Founders

2006: George Clooney

George ClooneyGettyImages

What We Wrote at the Time: “George Clooney first shot to fame in 1994 as medical heartthrob Dr. Douglas Ross on ‘ER.’ This ruggedly handsome bachelor has since made a seamless transition onto the big screen with starring roles in ‘Three Kings’ (1999), ‘O Brother, Where Art Thou?’ (2000), ‘Ocean’s Eleven’ (2001), and ‘Syriana’ (2005) — for which he was awarded a Best Supporting Actor Oscar and a Golden Globe. But Clooney is much more than a handsome man with solid acting chops. He’s also an accomplished writer and director, and his talent for these crafts were acknowledged when 2005’s ‘Good Night, and Good Luck’ — which he directed and wrote — received two Oscar nominations for Best Director and Best Screenplay. He made his mark in Oscar history as he became the first person to be nominated for directing one movie and acting in another in the same year.”

Does It Hold Up? Despite Clooney’s self-deprecation — a quote next to the above blurb reads, “I doubt anybody gets taken seriously for very long. I'll be on some reality show in about six years going, 'Hey, I had a great year in 2006.'" — he’s remained a force to be reckoned with in Hollywood ever since, stepping behind the camera for four more films and generally just remaining handsome, successful and famous. The high-profile marriage to Amal doesn’t hurt, either.

Runners-Up: Jay-Z, Richard Branson, Lance Armstrong, Tom Ford

2007: David Beckham

What We Wrote at the Time: “Global soccer icon David Beckham became the $250-million man when he (and wife Victoria) moved to Beverly Hills to play for the Los Angeles Galaxy of the MLS. Between his tremendous talent, English charm, stylish wardrobe and slick haircuts, Becks is single-handedly making soccer relevant stateside. Because of his achievements, he's been a consecutive AskMen.com list-topper, and has shown his appreciation by saying, ‘I am honored to be recognized once again by the AskMen.com community. I would like to thank everyone for their support.’”

Does It Hold Up? Somewhat — Becks retired in 2013, so he’s not exactly tearing it up on the pitch lately; arguable his star’s been outpaced by that of his wife, former pop star Victoria (aka Posh Spice) and her fashion line. Still, he’s rarely distant from the tabloid headlines thanks to his enduring hold on the collective imagination as a damn, damn handsome man.  

Runners-Up: Matt Damon, Timbaland, Roger Federer, Justin Timberlake

2008: Barack Obama

Barack ObamaGettyImages

What We Wrote at the Time: “For millions of young guys voting for the first time, Barack Obama isn’t a symbol of change — he is the emissary of their legacy. His arrival tells them that they aren’t doomed to inherit the archaic cynicism of their parents, but are free to entertain their own hopes and dreams. More so than his opponent, if Barack Obama wins, those first-time voters who supported him stand poised to claim fair credit for a watershed event in their country’s history, and thus to assume a greater responsibility for shaping its future. After all, American politics have not produced a candidate like him since 1960 — yet the comparisons with Camelot should end there; for Barack and the Obama family, there was no compound in Hyannis and no entitlements. His inspirational rise has revived another idea cynics tried to snuff out: that in America, how low you start out has no bearing on how high you can go. Win or lose come November, Barack Obama reminds us that the American Dream is real — real enough to believe in, and that it has no room for cynics.”

Does It Hold Up? Those words were written by someone who didn’t know whether Obama would become a historical footnote or the two-term president he went on to be, so they seem pretty prescient in retrospect. Sure, his legacy hasn’t looked the best since his successor took office, but his election did feel transformative and his presidency was unique, making him a damn strong pick here. 

Runners-Up: Steve Jobs, Michael Phelps, Robert Downey, Jr., Stephen Colbert

2009: Don Draper 

What We Wrote at the Time: “Don Draper may be a fictional character on AMC's ‘Mad Men,’ but he's just as real as any other public personality you can think of. Celebrities are brands, with carefully constructed images, and most of us are just as likely to have a beer with Don Draper as with anybody else on this list. What matters is that Draper's hardass 1960s persona represents something about male identity that is enduringly captivating, but has nonetheless vanished. The man that Don Draper is — value-driven and thoroughly masculine — is the product of a bygone era; without him, there would be no contemporary figure to represent it. Yet, as removed as his persona may be, it is also contemporary and familiar. He's a postwar archetype, both a brilliant career man and a temptation-swayed philanderer who sincerely wants to be a family man. Like most men, us and our fathers both, Draper is permanently conflicted over how to reconcile his morals and his desires.”

Does It Hold Up? The comments on this one were not kind — many readers were unfamiliar with Jon Hamm’s career-defining role and called him “Don Diaper” and “Don Gayper,” or ridiculed the concept of a fictional character taking the top spot — but ‘Mad Men’ is inarguably one of the best TV shows of the 21st century, and Draper’s portrayal of a specific type of masculinity is nothing short of iconic. 

Runners-Up: Usain Bolt, Barack Obama, Mark Zuckerberg, Simon Cowell

2010: Jon Stewart 

Jon Stewart GettyImages

What We Wrote at the Time: “While the U.S. wages war in the Middle East, Jon Stewart has been fighting his own brand of war in the vicious battleground of cable television, leading the charge of personalities and ideals against the behemoth, ultra-right American news media. Stewart may host his ever-popular ‘The Daily Show’ from behind a desk, but make no mistake — he’s on the front lines, and it’s getting ugly. This year, as in years past, there was no shortage of targets, from mainstays like Bill O’Reilly, Glenn Beck and Sarah Palin to a swath of newcomers including disgraced anchor Rick Sanchez, Christine O’Donnell, the emerging Tea Party movement, and all the critics who alleged that, behind closed doors, Stewart’s show was nothing but a sexist boys' club (they were wrong, by the way).”

Does It Hold Up? Click here. Enough said. 

Runners-Up: Bill Gates, Mark Zuckerberg, Steve Jobs, Kanye West

2011: Steve Jobs 

What We Wrote at the Time: “When Apple founder Steve Jobs passed away on October 5th, the worldwide outpouring of emotion befitted the death of a spiritual leader. But in the midst of mourning, people wondered, ‘Who is the next Steve Jobs?’ Some chose Mark Zuckerberg as the heir apparent, while others homed in on Google’s Larry Page. But the truth is, there is no ‘next Steve Jobs.’ There can’t be. Jobs was around when the world was changing faster than ever before, and he created the tools to help us keep up. His singular vision revolutionized the way we do, well, everything. Remember the first time you opened a MacBook or spun the iPod’s wheel, or the feeling you got when you held your first iPhone? It felt like you were holding a piece of the future. We were the ones around when Steve Jobs, like Thomas Edison and Henry Ford before him, changed the world. Thank you, Steve Jobs, for teaching us all how to think different.”

Does It Hold Up? Tabbing Jobs as the top man of the year in the months directly following his death was a touching and logical move, but it makes it trickier to evaluate his legacy. Apple is still chugging along — the world’s first trillion-dollar company, anyone? — but it hasn’t exactly replicated Jobs’ history of shaking up the whole tech industry every other year. 

Runners-Up: SEAL Team Six, Larry Page, Warren Buffett, Kanye West

2012: James Bond 

What We Wrote at the Time: “It’s official: 007 is No. 1. Ian Fleming’s dashing super-spy may have sipped his first martini in 1953, but James Bond has always fit right in with the times. Bond has changed with each actor’s interpretation of the role — from the smooth Sean Connery to the bare-knuckle brutishness of Daniel Craig — while always standing up for the same values. No matter how much the world has changed, what guy still doesn’t like a stiff drink, a sexy companion, a fast car and yes, the latest nifty gadgets? A connoisseur of the finer things in life, a ladies’ man and a hero who has saved the world many times over, James Bond has been influencing men for six decades, and he’s not done yet.”

Does It Hold Up? Don Draper as man of the year in 2009 made more sense than this, considering Bond as a character was a shade short of 60 years old for this Top 49, and had been played on screen by five other men prior to Craig taking on the job in 2006. The lackluster paragraph above makes you wonder what the hell AskMen’s editors were thinking when they (heh) pulled the trigger on this one. Still, 2012’s Bond film, “Skyfall” grossed over a billion dollars and was universally liked by critics, and Craig has stuck around for several more iterations. 

Runners-Up: Usain Bolt, Bill Clinton, Seth McFarlane, Joseph Gordon-Levitt

2013: Elon Musk 

Elon Musk GettyImages

What We Wrote at the Time: “One of the things that has always frustrated humanity is our inability to see past the veil of the present into the fog of the future. But every so often, someone with a piercing vision comes along — someone who can clearly see where everything is headed, and works tirelessly to ensure that that future comes about. We call men like these thinkers, innovators, geniuses; men like Thomas Edison, who brought us the telephone or Steve Jobs, who re-invented the way we interact with computers. It's fair to say that 2013 has made us aware of another man like this. Elon Musk, the CEO of Tesla Motors and SpaceX, has innovated in almost every realm imaginable. He co-founded PayPal, upended space exploration, made electric cars both sexy and viable and proposed what could be a revolutionary solution to America's slowly decaying highways, the Hyperloop. Elon Musk is so ahead of his time, in fact, that it's difficult to fully comprehend the extent of his influence. More than anyone else on this list, he is a true visionary.” 

Does It Hold Up? Yes and no. Musk hasn’t exactly been brought down by shameful details of his personal life; he’s still alive, and he’s still rich. However, the past six years haven’t been super kind to the South African and his companies. SpaceX rockets have exploded, Tesla’s struggled financially, the SEC is on his tail, and the Hyperloop appears to be going nowhere, fast. Maybe those visions we thought he was having were just hallucinations. 

Runners-Up: Jason Collins, Bryan Cranston, Chris Hadfield, Nelson Mandela

In 2014, AskMen switched the formula up a little, running an unranked list called “Great Men Give” that focused on charity efforts rather than star power or career success. DiCaprio wasn’t technically No. 1 on the list, but he was the only guy on the list’s main page, so it’s hard to argue that he wasn’t the face of the feature — and thus a fitting pick. 

2014: Leonardo DiCaprio

What We Wrote at the Time: “Leonardo DiCaprio, an award-winning actor and four-time Academy Award nominee, has been an outspoken advocate for environmental issues throughout his career. In 1998, at the age of 24, DiCaprio established his foundation with the mission of protecting the Earth’s last wild places and implementing solutions to build a more harmonious relationship between humanity and the natural world. Through grantmaking, public campaigns and media projects, DiCaprio has worked to bring much-needed attention and funding to three focus areas: protecting biodiversity, ocean and forest conservation and climate change.”

Does It Hold Up? Despite increasing flak he’s gotten for his pattern of near-exclusively dating 23-year-olds, he’s remained a force in the biz, finally picking up a Best Actor Oscar in 2016, and remains a force to be reckoned with in the entertainment industry. If you haven’t seen “Once Upon a Time in Hollywood,” you don’t know what you’re missing.

Runners-Up: Jamie Oliver, 50 Cent, Mark Zuckerberg, Hugh Jackman

After the prior year’s unranked “Great Men Give” list, AskMen switched up the formula again — this time for a more Top 49-like ranked list called “The Boss List,” which Curry topped. 

2015: Steph Curry

Steph CurryGettyImages

What We Wrote at the Time: “What Stephen Curry has been doing to the NBA just is not fair. He's not only figured out a way to usurp LeBron James for the title of World's Best Basketball Player, but he's also somehow made firing 3-pointers just as exciting as any slam dunk. His 37 points in Game 5 of the NBA Finals is now the stuff of legends. More incredible than his shooting abilities was the way he broke open the game and propelled the Golden State Warriors past LeBron James and the Cleveland Cavaliers to their first championship since 1975. Aside from being the league's MVP and most prolific scoring threat, Curry is locked into a lucrative deal with Under Armour through 2024. Nothing is stopping him.”

Does It Hold Up? He’s lost several times in the NBA finals in the past four years — so clearly, some things can stop him — but damn if Curry wasn’t a prescient pick as a guy we’d all still be talking about four years later, and a guy who nearly single-handedly changed the game of basketball. 

Runners-Up: JJ Abrams, Pope Francis, Dwayne “The Rock” Johnson, Elon Musk

2016: Michael Phelps

Like Leo two years prior, Phelps wasn’t technically No. 1 on this list — called the “Flex 50,” and focusing on athletes of all kinds — which was also unranked.

What We Wrote at the Time: “Whether or not you believe Michael Phelps is the greatest athlete of all time is completely up to you. But there’s no argument that he is the most accomplished athlete in Olympic history, with seven world records to his credit and 23 gold medals (28 medals overall). He finished his fifth Olympic Games in Rio by winning a record-breaking 13th individual gold medal, topping a record that stood for more than 2,000 years. ‘People have no idea how difficult it is to win one Olympic gold medal,’ his coach Bob Bowman told the Washington Post. ‘Michael has done it so frequently that it’s really hard to put it in perspective.’”

Does It Hold Up? Phelps was the first name on the list, and the hypothetical superlative tossed out in his blurb’s first sentence gives you an idea of why. It’s only been three years, but it’s hard to dispute any of this.  

Runners-Up: Mat Fraser, Conor McGregor, Usain Bolt, Ido Portal

OK, back to the realm of complete hypotheticals. Starting with...

2017: Dan Bilzerian

What We Might Have Written at the Time: “Love him or hate him, you can’t ignore him. Dan Bilzerian — the hard-partying, beard-sporting poker star — is the man AskMen readers crave more news about. Every time we publish a story detailing what crazy hijinx he’s up to lately (more often than not involving scads of cash, copious amounts of booze, bevies of scantily clad models and more high-powered guns than you can shake a barrel at) the men of the world flock to click on it. If you’re not sure why, well, what can we tell you but re-read that last sentence?”

Does It Hold Up? Mercifully, Bilzerian has slunk back to the primordial ooze whence he came. 

2018: Anthony Bourdain

Anthony BourdainGettyImages

What We Might Have Written at the Time: “You don’t need to be a snooty foodie to appreciate a cooking show, and no one exemplified that better than Anthony Bourdain. Ruggedly handsome, sharply intelligent and deeply, unrelentingly passionate about how and what we eat, Bourdain was an icon to many, and a role model for any man looking for a glimpse of what healthy masculinity looks like. Bourdain cared about real social issues, was protective of those less fortunate, owned up to his mistakes and the black marks of his past, and strove relentlessly to be a better man. That he cut his own life short is a tragedy, but that we got to see so much of who he was during his time on Earth is a blessing.” 

Does It Hold Up? We miss you, Anthony. Even in death, you were responsible for an enduring meme about how awesome you were. 

As for 2019, it’s too early to say who we will (would?) pick. Like every year, famous men are impacting the world, having career resurgences, experiencing mind-boggling financial success. Post-#MeToo, it feels like the men in the headlines are primarily the ones who’ve been accused of sex crimes; maybe future iterations of a Top 49 Men list will focus on non-famous guys who are making positive change in their communities instead, helping to instill healthy and uplifting versions of masculinity that’ll inspire future generations of boys to become the great — and kind — men they’re capable of being. 

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