Freddie Prinze Jr.
Best known as: Ray in the I Know What You Did Last Summer movies, Zack in She’s All That
Golden era: Late ‘90s and early ‘00s
Then: Freddie always played the BMOC you wanted to date. Oh, that smile! That dangerously spiky hair!
Now: Freddie took himself off the market when he tied the knot with his I Know What You Did Last Summer co-star Buffy Sarah Michelle Gellar in September 2001. The couple welcomed their first child, daughter Charlotte Grace, eight years later, and their second child, son Rocky James, in September 2012. As far as acting goes, Freddie hasn’t done a whole lot since his rom-com heyday, starring in two live-action Scooby-Doo films opposite his wife, headlining a short-lived series called Freddie, recurring on one season of 24, and voicing the Jedi Kanan in the animated series Star Wars Rebels. But hey, he was briefly on the "creative team" for WWE Raw in 2008, so that's... a thing.