Hilary Duff
Before starring as Sophie, Hilary was gushing over Ethan Craft (Clayton Snyder) and heading to Rome on school trips in Lizzie McGuire back in the early aughts. She is also known for her movie roles in A Cinderella Story, Cheaper by the Dozen, Cadet Kelly, Casper Meets Wendy, Material Girls, The Perfect Man, The Haunting of Sharon Tate, Flock of Dudes and Beauty and the Briefcase.
She also played Kelsey in the Sutton Foster-led series Younger and Olivia Burke in Gossip Girl.
Josh Peck
Hug me, brotha! Josh now plays Drew in How I Met Your Father, but fans may remember him as the hilarious Oprah-obsessed teen named Josh in Nickelodeon's Drake and Josh. He has also starred in TV series Turner and Hooch and Fuller House.
You may have also recognized his voice in Teenage Mutant Ninja Turtles, Lego Star Wars: All-Stars and Ice Age: Continental Drift.
Francia Raisa
Before playing Valentina on HIMYF, Francia starred in Secret Life of an American Teenager and Grown–ish, as well as movies including Bring it On: All or Nothing and Life Size 2.
Kim Cattrall
Kim may now be telling the story of how she met her son's father in HIMYF, but she is best known for her iconic role as Samantha Jones in HBO's Sex and the City.
But she has portrayed more than a cosmo-loving Manhattanite. She has also starred in Mannequin, Police Academy, Porky's, Star Trek VI: The Undiscovered Country and more.
Tien Tran
There's no denying Tien has a large range of acting abilities. Before joining Hulu's comedy sequel, she starred in the 2021 horror film Candyman, as well as TV shows including Showtime's Work in Progress, Hot Date and HBO Max's Southside.