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Sexiest Man Alive 2009: By the time Depp, 46, landed his second PEOPLE's Sexiest Man cover in 2009 (his first was in 2003), he was famous for his zany portrayal of Captain Jack Sparrow in the Pirates of the Caribbean movies, his non-Hollywood lifestyle (he and his family lived mostly in France) and his chiseled cheekbones.
Now: Depp just turned 50, which he's fine with, if only for the clothing options. "As you get older you can . . . wear anything you want; old people dress cool," jokes the actor, who has been stepping out with actress Amber Heard since his 2012 split from Vanessa Paradis.
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Sexiest Man Alive 2008: When the Aussie hunk won the title five years ago, there was one woman who made sure the honor didn't go to his (gorgeous) head: wife of 12 years Deborra-Lee Furness. "She said, 'Obviously, Brad wasn't available this year,'" Jackman, 40, recalled. "And I said, 'That was a joke, right?' "
Now: After starving himself to play the down-on-his-luck Jean Valjean in 2012's Les Misérables, for which he received an Oscar nod, Jackman, 45, went the other extreme for his role as Wolverine in the upcoming X-Men: Days of Future Past, with daily three-hour workouts and a bland 5,000-calorie diet. "I literally talk to myself like I'm training," he told Entertainment Weekly Radio. "'One more mouthful, come on man, you can do it."
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Sexiest Man Alive 2007: With two of the hottest movies of the year – The Bourne Ultimatum and Ocean's Eleven – under his belt, the 37-year-old Boston native got humble when he found out he won the coveted PEOPLE crown, er, cover. "You've given an aging suburban dad the ego-boost of a lifetime," Damon said. Which, of course, made him even sexier.
Now: His boyish good looks may have a touch of gray but the married father of four isn't fearful of aging, thanks to a still-busy Hollywood legend. The 43-year-old told Contactmusic.com, "Clint [Eastwood] makes the other side of the hill look pretty appealing."
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Sexiest Man Alive 2006: "There's a lot of pressure," Clooney, 45, joked about the Sexiest Man Alive honor. "There are all the events you have to show up for. The sash you have to wear … is embarrassing." He should know – he first won in 1997 when he was a dreamy doc on ER. What wasn't embarrassing: winning the Best Supporting Actor Oscar for Syriana that same year.
Now: Is the affable Clooney, 52, worried about aging in youth-oriented Hollywood? Nah. "I look at myself onscreen and go, 'I don't look like I did when I was 40 – I know that,' " he says. And it's okay. "I just loved the way [Paul Newman] handled growing old onscreen. It's understanding that you're now basically a character actor." Next up for the devoted bachelor: starring in and directing The Monuments Men with good buddy Matt Damon.
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Sexiest Man Alive 2005: Back then, audiences were flocking to see the charismatic actor in the action film Sahara, costarring then-paramour Penélope Cruz. But McConaughey's Texas-size sense of humor was an equal draw. Upon hearing he was crowned SMA, he said, "I like the 'Alive' part ... wait until you see the roles I could take after this."
Now: McConaughey, 44, hasn't let his surfer-dude good looks dictate his career. After playing a buff strip-club owner in Magic Mike, the married actor with three kids lost 47 pounds to portray an HIV patient in the upcoming Dallas Buyers Club.
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Sexiest Man Alive 2002: Affleck, 30, was engaged to Jennifer Lopez and filming the action-adventure flick Daredevil with another Jennifer – last name Garner – who gushed about him: "He's your basic tall, dark and handsome. He's it. You want him to save you. I can't imagine anyone the world would rather see swoop in and save the day than Ben."
Now: He did indeed swoop in – not to save the day but to marry Garner in 2005. Much-lauded for directing 2013's Best Picture Oscar winner Argo, the down-to-earth father of three, 41, will next dominate the big screen as Gotham's Caped Crusader in the upcoming Batman vs. Superman flick.
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Sexiest Man Alive 2001: No one knew how to battle bad guys in a tux better than Brosnan, whose James Bond carried on the tradition of martinis, fancy sports cars and beautiful women. In real life, the 48-year-old Irishman wasn't doing so bad either. "His real beauty emanates from the soul," enthused wife Keely Shaye Smith. "And, like a fine wine, he's aging beautifully."
Now: He hung up his Bond ambition when Daniel Craig took over the role in 2006. But Brosnan's kept busy with other movies, including Remember Me with Robert Pattinson and I Don't Know How She Does It with Sarah Jessica Parker. The actor, 60, recently shot the spy thriller November Man.
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Sexiest Man Alive 2000: Besides his second Sexiest Man title (the first was in 1995), Pitt, 37, received another much talked about designation in 2000 – Jennifer Aniston's Husband. And yet, with a hot career and an equally hot wife, he remained the polite Midwesterner. "What makes him really attractive is internal – his humor and caring and curiosity," said his Fight Club costar Helena Bonham Carter.
Now: He showed his nurturing side when fiancée Angelina Jolie, whom he met on the set of Mr. and Mrs. Smith in 2005, underwent a double mastectomy in February. The actor, 49, who is raising six kids with Jolie, also starred in and produced the Oscar-buzz-worthy 12 Years a Slave.
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Sexiest Man Alive 1999: Life was good for the actor. Onscreen Julia Roberts was galloping into his arms in Runaway Bride. Girlfriend Carey Lowell was pregnant with his first child. And, at 50, that head of silvery hair, the twinkling eyes and swagger were as potent as ever. But he had another gift: "He listens to you," said Laura Linney, his costar in 1996's Primal Fear.
Now: A practicing Buddhist for more than three decades, Gere, 64, hasn't lost any of his charisma (or hair). Though life is still good – the actor received a Golden Globe nom for last year's Arbitrage – he and Lowell split in September after 11 years of marriage.
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Sexiest Man Alive 1998: He’d made a career of being the go-to action hero – Indiana Jones, Han Solo, Jack Ryan – who always got the bad guy and the good girl. Something about his rugged looks and bemused wit drove women wild. But Ford, 56, didn't get it. "I never feel sexy," he said. "I have a distant relationship with the mirror."
Now: Still going strong at 71, Ford had featured roles in the recent Jackie Robinson biopic 42 and Anchorman 2: The Legend Continues. And if there’s ever an Indiana Jones 5, count him in. "I have strong ambition to do it while I'm still alive," he tells ExtraTV.
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Sexiest Man Alive 1996: What made the 42-year-old Oscar winner, known for his reserve, sexy? His Courage Under Fire costar Regina Taylor summed it up: "There's something going on behind the eyes that is at once very accessible, very vulnerable, but very mysterious," she said. "It's that mystery that you're attracted to."
Now: Washington, who's been in showbiz for 30 years, received his sixth Oscar nomination in 2013 for Flight; the 58-year-old also got a big compliment from Good Housekeeping recently, which called him a celebrity "getting sexier by the year."
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Sexiest Man Alive 1995: It wasn't Risky Business for PEOPLE to name the wildly popular actor the Sexiest Man. He was driving audiences crazy in the stock-car-racing adventure Days of Thunder. At the time, the 28-year-old actor was involved with his Thunder costar, Nicole Kidman, who would eventually become his wife.
Now: Though Cruise, 51, has built a career playing heroes in films like Top Gun and Mission: Impossible, he's lately been showing off other sides of his talent in movies like the action-comedy Tropic Thunder and the musical Rock of Ages.
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Sexiest Man Alive 1986: He was the handsome guy blowing up TVs across America with the gleaming grin, chiseled pecs and piercing blue eyes. Playing a compassionate plastic surgeon on St. Elsewhere came with an unexpected perk: "Women would come up to me and show me their breasts and ask for my opinion," said Harmon, 34. "And I gave it to them!"
Now: A veteran of TV's NCIS since it began in 2004, Harmon, 62, recently made headlines when it was revealed he used a sledgehammer to save a teenage boy from a burning car in Los Angeles 17 years ago, according to a CBS report. "I have no doubt that [if not for Harmon] I would not be alive," recounts the victim, Colin Specht, now 33.