Several roles followed throughout the 1980s, with appearances in the 1986 comedy The Whoopee Boys, and the award-winning Peggy Sue Got Married, with Kathleen Turner and Nicolas Cage.
In 1991, Jenney played waitress 'Lena' in Ridley Scott's Thelma & Louise; the following year, she appeared in American Heart, a film which earned her an Independent Spirit Award for Best Supporting Female.
During the nineties, she appeared in much smaller roles including Mr. Jones with Richard Gere, and Leaving Las Vegas, with Nicolas Cage and Elisabeth Shue, as well as Grace of My Heart.
Jane, with Demi Moore, Mad City, with Dustin Hoffman and John Travolta, Desert Blue, with Kate Hudson and Christina Ricci, Practical Magic, with Sandra Bullock and Nicole Kidman and The Deep End of the Ocean, which starred Michelle Pfeiffer and was based on the book by Jacquelyn Mitchard.
Some of her roles include Shoot First: A Cop's Vengeance, The Habitation of Dragons, A Stranger in Town, First Time Felon, the Emmy Award-winning If These Walls Could Talk 2, and The Pennsylvania Miners' Story.