6. James Van Der Beek (1977–2026)

Then: James Van Der Beek embodied teenage angst as Dawson Leery in Dawson’s Creek. The show was a cultural phenomenon, and his character’s emotional expressions even became one of the internet’s earliest memes (“Crying Dawson”). In the late 90s, Van Der Beek was at the peak of teen heartthrob fame.

Later years: Van Der Beek reinvented himself in surprising ways. He appeared in comedies like Don’t Trust the B— in Apartment 23, poking fun at his former fame, and joined Dancing with the Stars.

He focused on raising his six children with his wife and embracing a more grounded life, and his evolution from teen drama king to family man earned him a whole new level of respect. He died in February 2026 at 48, after a battle with colorectal cancer.