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Who didn’t have a crush on Ben Affleck back in the day?! Join Wonderwall.com as we celebrate the newlywed Oscar winner’s milestone 50th birthday on Aug. 15, 2022, with a look back at the best eye candy photos of Ben from earlier in his career… A tanned Ben Affleck showed off his swoon-worthy smolder — not to mention a razor-sharp jawline and dimpled chin — in 2001’s “Pearl Harbor.”
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How can someone be so handsome?! While many of us try to find our best angle before taking a photo, Ben’s always picture-ready! He’s seen here at the “Today” show in 1997.
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Ben Affleck made our hearts race with this adorable look in 2000’s “Bounce.”
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Ben Affleck looked laid-back and casually cute during this portrait session at Los Angeles’s Chateau Marmont in 1998.
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Name a hotter (fictional) astronaut… we’ll wait! Ben Affleck was the ultimate eye candy in 1998’s “Armageddon.”
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Who could forget this role? Ben Affleck played Will’s best friend, Chuckie Sullivan, in 1997’s “Good Will Hunting.”
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The way she looks at him! A very well-groomed Ben Affleck and Jennifer Lopez looked like the perfect pair when they attended the New York City premiere of her film “Maid in Manhattan” in 2002.
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Running errands has never looked so good! Ben Affleck showed off his charming good looks when he was photographed out and about in Los Angeles in 2000. He opted for a quintessentially ’90s and early 2000s look: a leather jacket with an open button-up shirt and tee underneath.
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A man who loves sports? Count us in! Ben Affleck is seen here during an NBA playoff game between the San Antonio Spurs and the Los Angeles Lakers in 2004.
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Did we particularly love this ‘do? Not exactly, but Ben Affleck still looked pretty good with ’70s hair when he played jerk Fred O’Bannion in 1993’s “Dazed and Confused.”
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Furrowed brows! Chiseled jaw! Mesmerizing eyes! Ben Affleck’s got it all. He’s seen here at the Los Angeles premiere of “Dogma” in 1999.
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At the Los Angeles premiere of “Good Will Hunting” in 1997, baby-faced Ben Affleck donned a slightly crumpled suit, a wide striped tie and neatly coiffed hair, which all added up to a lovably dapper look.
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We love how smitten Ben Affleck looks! At the 2005 Creative Arts Emmy Awards, a then newlywed Ben watched as first wife Jennifer Garner spoke on stage.
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We’ll never get over that smirk. Ben Affleck dressed up for the premiere of “Hollywoodland” during the BFI London Film Festival in 2006.
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Ben Affleck proved he’s what dreams are made of in this smoldering portrait taken at the Regency Hotel in New York City in 2000.
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In 1999, Ben Affleck starred in “Forces of Nature” alongside Maura Tierney (pictured) and Sandra Bullock. His charming good looks are reason enough to check out the rom-com!
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Ben Affleck, who’s seen here at the Los Angeles premiere of “Great Expectations” in 1998, sure looked suave in that leather jacket.
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In 2000, Ben Affleck and Matt Damon spoke during a Harvard Living Wage Campaign rally at Harvard University. Nothing’s more attractive than using your status to bring attention to an important cause!
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Who else swooned over Ben Affleck in this flick?! The actor, who’s seen here in 2004’s “Jersey Girl,” played the single dad of our dreams!
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What’s Ben Affleck thinking about? The tux-clad star looked pensive during an event he attended with his mom, Chris, in Boston in 1998.
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Happy Birthday, Matt! Ben Affleck showed some love for his best buddy, Matt Damon, during his 31st birthday celebration in 2001.
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At the 2003 Academy Awards, Ben Affleck looked happy — and bronzed — alongside then-fiancée Jennifer Lopez. We love their love!
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Ben Affleck turned heads at the New York City premiere of “Bounce” in 2000. We love how effortlessly he smizes!
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Once a Red Sox fan, always a Red Sox fan! A goateed Ben Affleck — who looked cute in his Boston gear — threw out the ceremonial first pitch before a Boston Red Sox vs. the Seattle Mariners MLB game at Fenway Park in 2003.
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Buzzcut Ben Affleck? We’re here for it. Ben’s seen here with a different ‘do at the premiere of “Good Will Hunting” in 1998.
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