Set in the 1930s, Woody Allen’s bittersweet romance CAFÉ SOCIETY follows Bronx-born Bobby Dorfman (Jesse Eisenberg) to Hollywood, where he falls in love, and back to New York, where he is swept up in the vibrant world of high society nightclub life.
Centering on events in the lives of Bobby’s colorful Bronx family, the film is a valentine to the movie stars, socialites, playboys, debutantes, politicians, and gangsters who epitomized the excitement and glamour of the age.
Bobby’s family features his relentlessly bickering parents Rose (Jeannie Berlin) and Marty (Ken Stott), his casually amoral gangster brother Ben (Corey Stoll); his good-hearted teacher sister Evelyn (Sari Lennick), and her egghead husband Leonard (Stephen Kunken). For the hooligan Ben, there are no questions that can’t be answered with brute force, but the others are more likely to ponder deeper matters, like right and wrong, life and death, and the commercial viability of religion.
Seeking more out of life, Bobby flees his father’s jewelry store for Hollywood, where he works for his high-powered agent uncle Phil (Steve Carell). He soon falls for Phil’s charming assistant Vonnie (Kristen Stewart), but as she’s involved with another man, he settles for friendship. Bobby also befriends Rad (Parker Posey), a model agency owner, and her husband Steve (Paul Schneider), a wealthy producer.
When Vonnie’s boyfriend breaks up with her, Bobby seizes the opportunity to romance her, and she ultimately returns his affections. When he asks her to marry him and move to New York, she is tempted, but things do not go as smoothly as planned.
Heartbroken, Bobby returns to New York, where he begins working for Ben, who has muscled his way into owning a nightclub. Bobby displays natural talents as an impresario and swiftly promotes the club into the hottest in town, renaming it “Les Tropiques.” Rad introduces him to the beautiful socialite Veronica (Blake Lively) and he courts her assiduously. Although he is still carrying a torch for Vonnie, when Veronica reveals she’s pregnant, they marry and begin a genuinely happy life together.
Everything seems to have fallen into place for Bobby until the night Vonnie walks into “Les Tropiques.”