Jenna made her television acting debut in 1986 appearing on an episode of ABC Weekend Special, then she appeared on shows like Tales from the Darkside and Kate & Allie acting out guest roles. She also co-starred in the sitcom Lenny although the show didn't last long. In 1989 she appeared in the feature film Born on the Fourth of July opposite Tom Cruise. Then there was Blossom from 1991 to 1995 portraying the role of Six LeMeure. I didn't think she was going to grow up and be extremely hot! She also is the voice of Stacey in A Goofy Movie in 1995. Then she attended the University of Southern Califonia for a couple years, but then she dropped out and returned to acting. From 1999 to 2004 she began to play the role of Stevie van Lowe in the Parkers. During that time Jenna played the voice of Trinket St. Blaire in the animated series Pepper Ann. In June 2000, Jenna recorded a demo compact disc (which honestly I have not heard yet) in an attempt to launch a recording career in country music. Her debut album, Breathing Room, was released on September 18, 2007.
In 2005 she appeared in Marsha Potter Gets a Life. Then she guest stared in a episode of Cold Case and parodied Lauren Graham's character of Lorelei Gilmore in the Family Guy episode Perfect Castaway. She was also the voice of Gracie in the feature Dr. Dolittle 3 which went straight to DVD.