Grossman also had a recurring role on the television series 10 Things I Hate About You, a reboot of the original cult classic movie of the same name.

[3] In 1999, Grossman was cast in her first major role, playing supporting character Mary Cherry in The WB high school drama series Popular.

[citation needed] After Popular, Grossman joined the cast of The WB sitcom What I Like About You with Amanda Bynes and Jennie Garth.

She appeared in two movies in 2006, Running with Scissors in an uncredited role and in Itty Bitty Titty Committee as Maude.

In 2017, she joined the cast of the seventh season of American Horror Story as Meadow Wilton and a flashback version of the infamous serial killer and Manson Family gang member Patricia Krenwinkel.