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1985: Despite his bad-boy reputation, Sean Penn – one of the decade's hottest young actors – exchanged vows with Madonna as paparazzi helicopters swarmed above. (Their media-circus marriage lasted until 1987.)
2005: No big wedding, no hovering photographers: Ben Affleck said "I do" with Jennifer Garner in June in a private ceremony. The parents-to-be have since embraced a domestic routine of coffee runs and quiet nights.
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1985: Boyishly cute Michael J. Fox lent hipster cred to young Republicanism (as Alex P. Keaton on Family Ties) and weird science (as Marty McFly in Back to the Future).
2005: With his indie-rock and comic-book obsessions, The O.C.'s own loveable misfit, Adam Brody, has made fast-talking fanboys hot. "The giggling, the pointing – girls freak out over him," one producer told PEOPLE.
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1985: The Brat Pack (including, from left, Andrew McCarthy, Emilio Estevez, Judd Nelson and Rob Lowe) were Hollywood's cool clique onscreen (in movies like St. Elmo's Fire and The Breakfast Club) and off.
2005: On HBO's Entourage, It boy Adrian Grenier (from left) only parties if pals Jerry Ferrara, Kevin Connolly and Kevin Dillon are invited, too. Before the foursome hit it big, "L.A. felt lonely," Grenier told PEOPLE.
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1985: After graduating from Brown, future SMA John F. Kennedy Jr. worked at nonprofits, toured the slums of India and even acted: His stage debut, at age 24 in the Off-Broadway show Winners, opened to a full house.
2005: St. Andrews grad Prince William carried on mum's philanthropic work as a volunteer in Chile. Now 23, the British royal will soon follow in his dad's military footsteps, attending the elite military academy Sandhurst.
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1985: Roger Moore, then 57, capped off his career as Her Majesty's most trusted agent, James Bond, in his seventh 007 thriller, A View to a Kill.
2005: Daniel Craig, 37, gets his license to kill as the newest – and blondest – Bond in Casino Royale, due next year. And he's ready for an ultra-cool Bond girl: He's starred opposite Sienna Miller (Layer Cake), Angelina Jolie (Tomb Raider) and Gwyneth Paltrow (Sylvia).
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1985: In the '85-'86 NFL season, Chicago Bears quarterback Jim McMahon won a Super Bowl title – and the nickname Mad Mac, thanks to his taste for mooning helicopters and partying with stars like Bruce Willis.
2005: After winning his second Super Bowl, New England Patriots QB (and former altar boy) Tom Brady donned a tux to escort fiancée Bridget Moynahan to New York City's chic Costume Institute Gala.
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1985: As Miami Vice's Sonny Crockett, the newly sober Don Johnson made pastels and a five o'clock shadow the year's fashion must-haves (PEOPLE even called him "Armani-ed and dangerous").
2005: Colin Farrell, playing Crockett in the big-screen remake of the show, sports the stubble – but he's no teetotaler. "After a long day's work, I can't just go home, get into bed and flip on Friends," he's said.
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1985: Richard Dean Anderson could foil bad guys with nothing but a wad of chewing gum and a few twigs on his hit show MacGyver. No wonder ex Sela Ward called him "sexy and intelligent."
2005: Naveen Andews is Lost's go-to castaway for transceiver building, doomsday-computer repairs and, on the show's Hawaii set, a tune or two. "He can play any song on his guitar," says costar Josh Holloway.
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1985: Bono – a budding activist dabbling with Amnesty International – led U2 at Live Aid, the concert that raised $160 million for African famine relief.
2005: Bono – who's worked tirelessly for Third World debt relief – performed with his band at Live 8 to raise awareness of African poverty and target $25 billion in aid. "Bono's in love with the world," concert organizer Bob Geldof told Time. "He wants to embrace it."
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