Film credit
James Gandolfini as Trupo is the standout what-if, with Ray Liotta, Brad Pitt, and Eddie Murphy also mentioned
Van Lathan selects Halle Berry; Wesley Morris and Bill Simmons select Eddie Murphy. Berry is credited with the film’s most durable breakout role, while Murphy is praised for an unusually mature, generous and vulnerable comic performance.
Robin Givens, David Alan Grier, Boyz II Men, Reginald Hudlin, P.M. Dawn, Strangé perfume and the three-man pool-game format receive yes votes; Eddie Murphy, Martin Lawrence, Toni Braxton, the 1992 Knicks and chitlins are rejected, while Black romantic comedies remain disputed.
Research attributes the concept to Eddie Murphy, describes Eartha Kitt’s objections and a deleted nude metal-detector gag, cites Jules and Jim as a structural influence, and explains how Lela Rochon’s feet were made less attractive.
Halle Berry was Reginald Hudlin’s preferred Angela and Eddie Murphy ended the search after her screen test; Paramount executives resisted Robin Givens, with Vanessa Williams held as the backup for Jacqueline.
Halle Berry’s performance receives the final first choice; Jeffrey Holder’s ad pitches, the Martin television origin story, period slang, Eddie Murphy’s reactions and clothes, the role reversal, Strangé ads, Star Trek riff, Angela’s breakup, and the heartbreak-and-recovery arc are also praised.
The opening lunch's homophobic and transphobic material is identified as an element that has not aged well.
John Witherspoon’s entire dinner sequence is Bill Simmons’s and Van Lathan’s selection; Wesley Morris chooses Grace Jones’s first perfume-boardroom scene. The lunch, Lady Eloise encounter, Robin Givens flirtation, art class, pool game and rooftop reconciliation remain major alternatives.
The podcast explicitly reports Roger Ebert gave Boomerang three stars and quotes his view that Eddie Murphy had returned to form as a gentler, character-building comic actor.
Eddie Murphy Delirious joke about leaving a haunted house reportedly inspired title and premise; commentary observations read secondhand from an internet article.
