By Jessica Wedemeyer
1:50am PST, Mar 6, 2017
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 41 on March 8, 2017, Wonderwall.com is 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 of him at the 1997 premiere of "The House of Yes," his second film (following 1996's "To Gillian on Her 37th Birthday").
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We all fell in love with Freddie Prinze Jr. when he starred as Zack Siler in 1999's "She's All That." Doesn't this shot of him in his high school letter jacket take you back?
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It was a gathering of late '90s "It" couples during the ninth annual MTV Movie Awards in Los Angeles on June 3, 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!
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!
Freddie Prinze Jr. joined real-life love Sarah Michelle Gellar and her "Buffy the Vampire Slayer" co-star Michelle Trachtenberg on the red carpet during the 2001 Teen Choice Awards in Universal City, California, on Aug. 12, 2001. All three were nominated for awards that year.
Freddie Prinze Jr. sported an oh-so-'90s 'do while posing with co-star Brandy (another staple of the times) during the 1998 premiere of "I Still Know What You Did Last Summer."
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 on Dec. 22, 1998.) If you can listen to "Kiss Me" without experiencing some major feels, you probably weren't alive during the late '90s!
A platinum blond Freddie Prinze Jr. supported his real-life love Sarah Michelle Gellar on the red carpet during the 2001 Golden Globe Awards when she was nominated for Best Performance by an Actress in a Television Series – Drama for her work on "Buffy the Vampire Slayer" — which is basically our favorite show of all time!
Freddie Prinze Jr. wore quite the ensemble (print suspenders with a contrasting print tie — eep!) during the very first Teen Choice Awards on Aug. 1, 1999.
A rising star named 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 teenybopper romantic comedy.
Jinkies! So many icons in one photo! Remember when Freddie Prinze Jr. brought Fred Jones — our favorite blond mystery-solving cartoon character — to life in 2002's "Scooby-Doo," the live-action adaptation of the legendary animated series?
Freddie Prinze Jr. sported a totally '90s look — loose-fitting jeans, a short-sleeved button-down and a spiked hairdo — during the 1998 premiere of "Shakespeare in Love." (He'd be banned from the red carpet if he tried to attend a modern-day event in this getup!)
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: Netflix. Now.)
Aww! Freddie Prinze Jr. was just 19 years old when he walked the red carpet during the 1996 Golden Globe Awards. Ten months later, he made his feature-film debut in "To Gillian on Her 37th Birthday."
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.
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?!
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 platinum blond hairdos.
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.)
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."
