Jenna began her acting career in 1986, appearing in the television film The Kingdom Chums: Little David's Adventure and guest-starring in an episode of Tales from the Darkside. Jenna has appeared in several television series such as Blossom, in which she played the character Six LeMeure, Family Values, in which she played Phoebe Huck, and The Parkers, as quirky sidekick Stevie van Lowe. She also provided the voice of Stacey in A Goofy Movie and the voice of Trinket St. Blaire in Pepper Ann. She most recently appeared on an episode of Cold Case, and was a voice actor on Family Guy.

In June 2000, Jenna recorded a demo CD in an attempt to launch a recording career in country music. In 2004, she posed for a seductive spread in King Magazine.