Dealing with a troubled marriage to a drug addict, she finds solace in the genuine friendship of Robert Benchley, a colleague at Vanity Fair.

Amidst depression, Dorothy attempts suicide, but Robert intervenes, choosing not to pursue a romantic involvement due to fear of potential heartbreak.

Given the historical impact of many of the people portrayed in the film, the ensemble nature of the cast led to opening credits displaying all 30 actors listed above.

Director Alan Rudolph was fascinated with the Algonquin Round Table as a child when he discovered Gluyas Williams' illustrations in a collection of Robert Benchley's essays.

[4] After making The Moderns, a film about American expatriates in 1920s Paris, Rudolph wanted to tackle a fact-based drama set in the same era.

He began work on a screenplay with novelist and former Washington Star journalist Randy Sue Coburn about legendary writer Dorothy Parker.

In 1992, Rudolph attended a Fourth of July party hosted by filmmaker Robert Altman, who introduced him to actress Jennifer Jason Leigh.

"[3] Altman used his clout to persuade Fine Line Features and Miramax—two studios he was making films for—to team, with the former releasing Mrs. Parker and the Vicious Circle domestically and the latter handling foreign distribution.

[6] During the film’s 40-day shoot, the cast stayed in a run-down hotel dubbed Camp Rudolph and engaged in all-night poker games.

In addition, the actress listened repeatedly to the two existing audio recordings of Parker in order to perfect the writer's distinctive voice.