By Jessica Wedemeyer
12:00pm PST, Mar 8, 2023
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Freddie Prinze Jr. starred in some of the greatest teen fare of the late '90s and early '00s — iconic flicks such as "I Know What You Did Last Summer," "She's All That" and "Scooby-Doo." In honor of one our first celebrity crushes turning 47 on March 8, 2023, we're taking a look back at some of the most nostalgia-inducing photos of Freddie during the early years of his career when he was the king of Young Hollywood. Keep reading to relive his glory days, starting with this shot…
Freddie Prinze Jr. looked super-cute in glasses at the 1997 premiere of "The House of Yes," his second film (his first was 1996's "To Gillian on Her 37th Birthday").
MORE: The hottest photos of a young John Travolta
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We love their love! Freddie Prinze Jr. and then-girlfriend Sarah Michelle Gellar were a picture-perfect pair at the New York City premiere of his film "Boys and Girls" in 2000.
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Have you seen a look more '90s than this? We think not! In 1999, a 23-year-old Freddie Prinze Jr. attended the Los Angeles premiere of the thriller movie "End of Days" in an oversized gray sweater, baggy gray pants and dark blue sneakers.
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Freddie Prinze Jr. is seen here with actress Selma Blair, who's one of wife Sarah Michelle Gellar's best friends, at the premiere of the sci-fi horror movie "Existenz" in 1999.
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It was a gathering of late-'90s "it" couples during the ninth annual MTV Movie Awards in Los Angeles in 2000. Freddie Prinze Jr. and Sarah Michelle Gellar caught up with then-couple Katie Holmes and Chris Klein during the show. While Freddie and Sarah tied the knot in 2002, Katie and Chris parted ways in 2005 following an engagement of just over a year. So many memories!
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Freddie with a buzzcut? We love it! The Hollywood hunk is seen here at the Los Angeles premiere of the Nicole Kidman-led horror movie "The Others" in 2001. Love the glasses too, Freddie!
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Freddie Prinze Jr. was the perfect date when he attended the Los Angeles premiere of "The Grudge 2" — in which his missus, Sarah Michelle Gellar, starred — in 2006. Just look at the way she looks at him!
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Freddie Prinze Jr. cozied up to on-screen love Jennifer Love Hewitt in 1998's "I Still Know What You Did Last Summer." The slasher sequel opened during the height of J.Love's reign as Hollywood's leading teen screen queen, making them quite the pair!
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Freddie Prinze Jr. melted hearts with his signature smirk when he appeared on MTV's "Total Request Live" in 2002 with his "Scooby-Doo" castmates.
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Freddie Prinze Jr. joined real-life love Sarah Michelle Gellar and her "Buffy the Vampire Slayer" co-star Michelle Trachtenberg on the red carpet at the 2001 Teen Choice Awards in Universal City, California, in 2001. All three were nominated for awards that year.
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If you're a Freddie Prinze Jr. and Sarah Michelle Gellar stan like us, then chances are you've already seen this ridiculously cute photo. The Hollywood couple is seen here during a New York Knicks vs. Miami Heat NBA playoff game at NYC's Madison Square Garden in 2000.
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Freddie Prinze Jr. sported some oh-so-'90s hair while posing with co-star Brandy at the 1998 premiere of "I Still Know What You Did Last Summer."
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Freddie Prinze Jr. and Rachael Leigh Cook appeared in the music video for Sixpence None the Richer's "Kiss Me" after it was featured in their film "She's All That." (They shot the clip in Los Angeles in 1998.) If you can listen to "Kiss Me" without experiencing some major feels, you probably weren't alive during the late '90s!
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Co-stars reunite! Freddie Prinze Jr. was all smiles when he posed for a photo alongside "She's All That" co-star Kevin Pollak — who played the father of Rachael Leigh Cook's Laney Boggs — at a 2002 party.
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A bleached-blonde Freddie Prinze Jr. supported real-life love Sarah Michelle Gellar on the red carpet at the 2001 Golden Globe Awards when she was nominated for best actress in a TV drama series for her work on "Buffy the Vampire Slayer" — which is basically our favorite show of all time!
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Freddie Prinze Jr. hit the red carpet with his "Scooby-Doo" co-stars Matthew Lillard, wife Sarah Michelle Gellar and Linda Cardellini during the flick's Los Angeles premiere in 2002.
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Freddie Prinze Jr. wore quite the ensemble — printed suspenders with a contrasting printed tie) during the very first Teen Choice Awards in 1999.
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Rising star Paul Walker appeared alongside Freddie Prinze Jr. in 1999's "She's All That." Just two years later, a little film called "The Fast and the Furious" opened in theaters. The rest is history, but it all started with this beach volleyball scene from the teen romantic comedy.
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Four months before Freddie Prinze Jr. and Sarah Michelle Gellar tied the knot, they took the stage together during the Nickelodeon Kids Choice Awards in 2002!
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Jinkies! Two icons in one photo! Remember when Freddie Prinze Jr. brought Fred Jones — our favorite blonde mystery-solving cartoon character — to life in 2002's "Scooby-Doo," the live-action adaptation of the legendary animated series?
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Freddie Prinze Jr. sported a totally '90s look — loose-fitting jeans, a short-sleeved button-down and a spiked hairdo — at the premiere of "Shakespeare in Love" in 1998.
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It was a "Buffy the Vampire Slayer" reunion during the Los Angeles premiere of "Scooby-Doo 2" in 2004! Freddie Prinze Jr. and his real-life leading lady, Sarah Michelle Gellar, posed for photos with "BTVS" alum Seth Green during the premiere of the second "Scooby-Doo" flick, in which the Hollywood couple starred. (Fun fact: Seth and SMG are still close friends to this day!)
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Yowza! Freddie Prinze Jr. and a midriff-baring Jessica Biel raised temperatures in their 2001 baseball-themed rom-com "Summer Catch." (If you somehow missed this gem: Apple TV. Now.)
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Aww! Freddie Prinze Jr. was just 19 when he walked the red carpet at the 1996 Golden Globe Awards. Ten months later, he made his feature film debut in "To Gillian on Her 37th Birthday."
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Freddie Prinze Jr. joined forces with a familiar face for 1996's "To Gillian on Her 37th Birthday" — Claire Danes! (The film debuted just two weeks before her blockbuster flick "Romeo + Juliet" hit theaters.)
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Are those Transitions lenses in your glasses, Freddie Prinze Jr.? Our favorite leading man of the early aughts was like a warm ray of sunshine on the red carpet during the 2002 MTV Movie Awards.
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Freddie Prinze Jr. did his best pensive stare while starring in the 2000 romantic comedy "Boys and Girls." Do you understand now why we were so obsessed?!
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In 2001, Sarah Michelle Gellar supported hubby Freddie Prinze Jr. when she attended the Los Angeles premiere of his baseball-themed rom-com "Summer Catch."
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Freddie Prinze Jr. reunited on screen with wife Sarah Michelle Gellar, Linda Cardellini and Matthew Lillard in 2004's "Scooby-Doo 2: Monsters Unleashed." Fortunately, the sequel marked his final partnership with Canadian tuxedos and blonde hairdos.
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Freddie Prinze Jr. took home the surfboard for choice movie actor during the 2000 Teen Choice Awards. Wasn't he dreamy? (We probably voted for him, TBH.)
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What do you get when the male star of "She's All That" teams up with the female star of "10 Things I Hate About You"? Magic! That's exactly what happened when Freddie Prinze Jr. and Julia Stiles played lovers in 2000's "Down to You."
