Taylor began her acting career in 1989 on the Nickelodeon children's television series "Hey Dude" where she played the lifeguard Melody Hanson. She continued in that role through 1991 while making various guest appearances on other programs. In 1995, Taylor was cast as Marcia Brady in "The Brady Bunch Movie" and later in "A Very Brady Sequel". Following "The Brady Bunch Movie", Taylor made several comedic guest appearances on the TV series "Ellen", landing the lead role in the television series "Party Girl", based on the 1995 film of the same name, and more guest appearances on "Seinfeld" and "Friends". She played the racist school bully Laura Lizzie in the 1996 horror film "The Craft", and also played Drew Barrymore's cousin, Holly Sullivan, in the 1998 comedy "The Wedding Singer". In 2001, she starred alongside her husband Ben Stiller in "Zoolander".