Brest got his big break in 1984 with Beverly Hills Cop, starring Eddie Murphy. The film grossed over $300 million and received a Golden Globe nomination for Best Motion Picture – Comedy or Musical, as well as an Academy Award nomination for Best Original Screenplay.
It was six years before Brest would return with Meet Joe Black, a remake of Death Takes a Holiday, starring Brad Pitt and Anthony Hopkins. The film received mixed reviews and while it had a disappointing domestic box office return of $44,619,100, it fared much better overseas, taking in an additional $98,321,000 for a worldwide total of $142,940,100.
In 2003, Brest wrote and directed Gigli, starring Ben Affleck and Jennifer Lopez. After a protracted battle between studio and director, a radically revised and re-shot version of the original film was released. It became a notorious flop, with a scathing critical reception and disastrous box office performance. In the ensuing years since its release, Gigli has frequently been cited as among the worst movies ever made.
In 2009, his New York University student film, Hot Dogs for Gauguin, was one of 25 films chosen by the National Film Registry of the Library of Congress to "be preserved as cultural, artistic and/or historical treasures".