Charley Pearl [Alec Baldwin] is the heir to a toothpaste empire, a carefree playboy who does not work and fills his days with speedboats, luxury cars, and carefree hobbies. He is engaged to Adele Horner [Elisabeth Shue], the daughter of Lew Horner [Robert Loggia], a foul-mouthed, hot-tempered Hollywood studio mogul who grows wary of Charley’s apparent lack of ambition and guilt about it.
For a quick Las Vegas bachelor fling, Charley rounds up his four closest friends — Phil Golden [Paul Reiser], Sammy [Fisher Stevens], Tony [Peter Dobson], and George [Steve Hytner] — and agrees to foot the bill, even as he yearns to get back home to Adele. Their road trip stops briefly at El Rancho Vegas, where a glamorous singer named Vicki Anderson [Kim Basinger] disrupts Charley’s thoughts of wedding bliss. Charley cannot resist trying to woo her after her performance, but he’s warned that she belongs to somebody else. Vicki, however, responds to Charley’s charm and makes a risky proposition: she leaves a window open at her house for him to visit. The night ends with them in bed, a moment that is interrupted when Bugsy Siegel [Armand Assante], the notorious gangster and hitman who is also involved with Vicki, discovers them.
Bugsy toys with the notion that he’ll whisk Vicki and Charley to a midnight justice-of-the-peace wedding just for the thrill of it. Charley drives Vicki back to California and offers to cover her expenses, but she walks out anyway. To complicate matters, Charley’s actions become a tabloid headline: the wedding photo of Charley with Vicki appears on the front page while his engagement to Adele Horner runs on a later page. Charley apologizes, insisting he still wants to marry Adele, and he agrees to seek an annulment from Vicki and to donate a substantial sum to charity if he dares disappoint Horner again.
Charley’s near-miss with monogamy recurs when he runs into Vicki once more and cannot help himself; he remarries her, once again abandoning his fiancée. Lew Horner’s anger simmers to the brink, and he stops just short of violence, sending a couple of thugs to beat Charley and toss him into a swimming pool. Vicki’s career moment seems possible when an offer lands in her lap, yet Charley’s personal upheaval balloons: his father dies, and he is summoned to Boston to run the family business.
Vicki spends two years in Boston, navigating high society and the dull routines of tea parties, hoping Charley will eventually return to California and to her career. But Charley reneges on his promises, and Vicki ultimately ends their marriage in divorce. The couple’s paths cross again in a nightclub where Vicki has aligned with another shady figure, and a violent confrontation erupts. Charley wrenches Vicki away and, for a third time, marries her. As a grand gesture, Charley sinks millions into a movie studio intended to produce pictures starring his wife.
Meanwhile, the fortunes of Charley’s friends begin to rise in the film world, but Charley’s own fortunes slip into decline, and he ends up broke as his relationship with Vicki continues to fracture. She leaves him once more, and he is left to pick up the pieces. In a later moment, Charley is found at a nightclub, telling his friends that he has discovered a new line of work: computers. He gestures toward the stage where Vicki performs and reveals a diamond engagement ring he has kept, signaling a possible new chapter.
As the story moves toward its close, Vicki returns to the spotlight and, in a final gesture, slides the diamond engagement ring onto her finger, a quiet sign that love, ambition, and luck may still interweave in this turbulent tale of fame, fortune, and flirtation.
