Freddie Prinze Jr.
I Know What You Did Last Summer (and its sequel), She's All That, Down to You, Boys and Girls, Summer Catch...we dare you to name a more in-demand leading man in the late '90s and early aughts!
After his string of romantic comedies, Prinze, who is the son of actor Freddie Prinze, took on the role of Fred Jones in the Scooby-Doo franchise's 2002 and 2004 live-actions, starring opposite his wife Sarah Michelle Gellar. He also made a memorable guest appearance as Rachel's male nanny on Friends and fronted his own shortlived sitcom Freddie.
A massive wrestling fan, the 45-year-old worked as a WWE commentator in 2008 and as a producer in 2010. For four years, Prinze voiced Jedi Kanan Jarrus in Star Wars Rebels and he most recently appeared on Peacock's Punky Brewster reboot.
After welcoming daughter Charlotte in 2009 and son Rocky in 2012, Prinze and Gellar will celebrate their 20th wedding anniversary next year.
Jessica Biel
Summer Catch was the 7th Heaven star's first leading film role, with major movies such as The Texas Chainsaw Massacre and Blade: Trinity to follow.
Biel would also go on to appear in The A-Team, New Year's Eve, Total Recall, Hitchcock and A Kind of Murder before returning to the small screen as executive producer and star of The Sinner in 2017.
"There wasn't like a driving force behind it. I got on a path of doing films. But, as we all know, the film industry has become very limited. I wanted to take control of my career again, which is what I had in mind when I started this small production company," she explained to The Hollywood Reporter of forming Iron Ocean Productions with her good friend Michelle Purple. "Also, television was changing: It's become such an incredible place where if you have a thought-out, interesting, fresh idea, you have a great opportunity, especially as a woman, to put something on television."
But since her lead role in the splashy first season, the 39-year-old has focused largely on voice work (BoJack Horseman, Pete the Cat) and the 10-part crime series Limetown.
After five years of dating, Biel and Justin Timberlake got married in 2012 and have since welcomed two sons, Silas, 5, and Phineas, 13 months.
Wilmer Valderrama
The That '70s Show star made his film debut as baseball player named Mickey Dominguez.
After the hit Fox sitcom came to an end in 2006, Valderrama went on to co-star in the short-lived Awake, fronted From Dusk Till Dawn: The Series and joined NCIS as a series regular in 2016. He's also lent his voice to animated films Onward and Prince Charming.
After high-profile romances with Mandy Moore, Ashlee Simpson and Demi Lovato, the 41-year-old actor got engaged to model Amanda Pacheco in January 2020. The couple welcomed their first child together in February of the following year.
Matthew Lillard
While the Scream alum played Prinze's romantic foil in She's All That, Lillard was his trusted catcher Billy Brubaker in Summer Catch. And the 2001 movie wouldn't be the last time the two actors worked together, going on to star in 2002's Scooby-Doo and its sequel two years later. Lillard continued to provide the voice for Shaggy Rogers in animated outings.
Lillard went on to appear in Without A Paddle and The Descendants and made memorable guest appearances on Criminal Minds, The Good Wife and Twin Peaks. From 2018 to 2021, he co-starred in the NBC drama Good Girls and he'll next appear in He's All That, Netflix's reimagination of the 1999 classic, though he won't be playing aspiring MTV VJ Brock Hudson.
The 51-year-old married Heather Helm in 2000 and the couple have three children.
Gabriel Mann
The same year he appeared as Ryan's best friend Auggie Mulligan, Mann also co-starred in the now-cult classic Josie and the Pussycats, so big year for him!
The 49-year-old went on to appear in the Jason Bourne film franchise and enjoyed a recurring part on Mad Men before landing his breakout role as Nolan Ross on ABC's Revenge in 2011. After the drama ended four years later, Mann popped up on Ray Donovan, Hawaii Five-0 and is currently playing the DC villain Hush on The CW's Batgirl.
Marc Blucas
Blucas co-starred as teammate Miles Dalrymple shortly after his two-season stint as Riley Finn on Buffy the Vampire Slayer came to an end. He'd go on to appear in films such as We Were Soldiers, View From the Top and The Jane Austen Book Club and starred on USA Network's Necessary Roughness. The actor has since become a regular feature in Hallmark Channel's popular original movies.
The 49-year-old has been married to journalist Ryan Haddon since 2009 and the couple have two children together.
Beverly D'Angelo
Best known for her work as Ellen Griswold in the iconic National Lampoon's Vacation movies, D'Angelo has the uncredited role of Lusty House Mother in Summer Catch. She'd later have memorable guest appearances on Law & Order: SVU, Entourage and Mom.
D'Angelo was in a relationship with Al Pacino for seven years, with the couple welcoming twins Olivia and Anton in 2001 before splitting in 2003.
The 69-year-old Oscar-nominated actress reprised her role as Ellen in Vacation, the 2015 addition to the franchise starring Ed Helms and Christina Applegate. Around the same time, she and co-star Chevy Chase were looking to make a TV show together titled Chev & Bev that would find them playing grandparents whose plans for retirement are thrown for a loop when have to raise their grandchildren. While ABC initially ordered a pilot, they chose not to pick it up to series.