The Best Of: Freddie Prinze Jr. From 1998-2001

If there is one thing that defined the movies from our formative teenage years, it was probably that they were terrible. Think about it: The ’80s had John Hughes, the ’90s had Kevin Smith and Richard Linklater, and the new millennium had … American Pie? Not Another Teen Movie? Drumline? Yikes. The ’90s were edgy, Winona Rider, Daria, and goth. The ’00s were toothless, Kirsten Dunst, and our prom king was Freddie Prinze Jr. , the romantic lead that throughout the late ’90s and early 2000s who was so innocuous that sometimes you forgot he was in the movie at all. Below, we take a look at that goofy guy who we may or may not have had a crush on, and what his legacy in teen films has left us.

She’s All That

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The game-changing FPJ role. Even though this clip has an unrelated song over it, it captures the pivotal moment that would change the way teens said “Was I a bet?” in the 2000s…by adding curse words.

Down To You

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Julia Stiles and Freddie Prinze Jr. were two bankable stars in the early aughts, so it would seem natural to put them together. Unfortunately, the leads of Down To You had less chemistry together than you would think humanly possible. This film is also notable because Freddie Prinze drinks shampoo in a pseudo-suicide attempt and talks to spiders.

Boys And Girls

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Haha, we don’t even remember what this movie was about, but there is definitely an early 2000s/slacker/Kevin Smith-esque thing going on with this dialogue. Laundry as metaphor for your broken college relationship? Perfect.

Head Over Heels

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This movie was like Rear Window, if Rear Window was a rom-com starring Monica Potter. (Who? Exactly). Freddie had to display a wide range of skills for this film, as both a super rich, lovable art dealer and a possible psycho murderer. So basically, he had to be the cute version of Patrick Bateman. *No spoilerz* but yeah it turns out Freddie like brutally murdered eight women to get into character for this film.

Summer Catch

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IMDB summary: “A rich girl whose family summers on Cape Cod has a romance with a local poor boy who hopes to become a major league baseball player.” Translation: Freddie making terrible speeches in a Boston accent that would put Leo to shame.

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