Douglass's known acting career spanned 21 years, from 1978 to 1999. She was featured in the films Breaking Away, Romantic Comedy, and The Lonely Guy, and she had a recurring role on the television series Galactica 1980. Before all this, she had appeared on the cover of the December 1974 edition of Playboy.

Nude and erotic photos of Douglass also appeared in the 1981 edition of Hustler, which led to her filing a lawsuit against the magazine. In the suit she claimed that the photos were published without her permission and portrayed her in a false light, including as a lesbian, which damaged her career as an advertising model. A jury ruled in her favor, but in 1985 the United States Court of Appeals for the Seventh Circuit reversed the judgement and ordered a new trial. The United States Supreme Court let the order stand without comment.

In 1984, Douglass appeared in the fact-based made-for-television comedy-drama film Her Life As A Man, an adaptation of "My Life As A Man," an article Carol Lynn Mithers had written for the Village Voice. Her character, Carly Perkins, was an aspiring female reporter who sought a sportswriting job on a national magazine whose Editor was infamously chauvinistic, and she disguised herself as a man, using the alias of Carl Parsons, convincingly enough to be able to get the inside story she wanted.

On December 2, 2000, Douglass became Robyn Halprin when she married Criminal defense attorney Rick Halprin, who was known for the high-profile clients, including Chicago crime boss Joseph Lombardo, whom he represented.

In 2002, the Halprins sued Prairie Single Family Homes of Dearborn Park Association under the Civil Rights Act of 1968, claiming that the neighborhood association was allowing harassment of the couple because Halprin was Jewish. In 2004, in a decision much-debated among attorneys, the United States Court of Appeals for the Seventh Circuit reversed part of a lower court's dismissal of the case on narrow grounds. Douglass later divorced Halprin.