She has appeared in films including Lost Highway, Two Girls and a Guy, First Love, Last Rites (all 1997), Urban Legend, Another Day in Paradise (both 1998) and High Fidelity (2000).

[6] She is distantly related by marriage to baseball player Tim Lincecum on her mother's side.

Following that film she starred in several TV movies including Modern Vampires, Hefner: Unauthorized, and The Shaggy Dog.

That same year she guest starred in an episode of Ally McBeal and co-starred with Vincent Kartheiser, James Woods and Melanie Griffith in Larry Clark's crime drama Another Day in Paradise.

To avoid an NC-17 rating, a rough sex scene with Kartheiser had to be removed from the theatrical version.

[10] In 2000, Gregson Wagner had roles in Stranger Than Fiction, and High Fidelity opposite John Cusack.

In 2001, she was regular cast member in the short-lived prime time soap opera, Pasadena.

In 2020, Gregson Wagner produced the documentary film Natalie Wood: What Remains Behind, directed by Laurent Bouzereau.