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Charley Pearl is the heir to a toothpaste empire's fortune. He is a playboy who doesn't work for a living, spending his time indulging in hobbies like speedboats and fast cars. Charley is engaged to be married to the daughter of Lew Horner, a foul-mouthed, hot-tempered Hollywood studio mogul. Horner is concerned that Charley has no ambition of any kind and no apparent guilt about it. The studio chief warns Charley that if he should make Adele unhappy in any way, there will be hell to pay.
His four best friends—a comedian, a songwriter, a singer and a baseball manager (none particularly successful as yet)—accompany Charley on a drive to Las Vegas for a final bachelor's fling. Charley is willing to foot the bill for Phil, Sammy, Tony and George but is eager to get back home to his fiancee. They make a quick stop for a drink at a nightclub where Vicki Anderson, a glamorous singer, immediately disrupts Charley's thoughts of wedded bliss. He tries to pick up Vicki after her performance but is sternly warned that she belongs to somebody else. Vicki responds to Charley's charm, however, and obligingly offers to leave a window open at her home. Charley shows up and they end up in bed, only to be caught in the act by her other lover—Bugsy Siegel, the notorious gangster.
Rather than react violently, Bugsy amuses himself with the notion that he will take the scared-stiff Vicki and Charley to a justice of the peace in the middle of the night and make them marry one another. Charley drives her back to California and offers to pay her expenses, but Vicki walks out, wanting nothing more from him. In the meantime, their wedding photo pops up on the front page of the morning newspaper—with Charley's engagement announcement to Lew Horner's daughter appearing on a later page, as the enraged studio boss points out. Charley apologizes and still wants to marry a sobbing Adele. He agrees to get an annulment from Vicki and to pay a considerable sum to charity if he should dare disappoint Horner's daughter again.
Charley accidentally runs into Vicki again and can't help himself. Charley remarries Vicki and once again leaving his fiancee in the lurch. Lew Horner stops just short of killing Charley, instead sending a couple of thugs to beat him and toss him into a swimming pool. Charley accepts this as fair. Vicki is happy, too, momentarily, coming home with an offer that could advance her career, only to learn that Charley's father has died and he is needed on the other side of the country in Boston, where he is now expected to run the family's business.
Vicki puts her career on hold and spends two years in Boston, enduring high society and boring tea parties. She can't wait to get back to California and her career, but when Charley reneges on his promise, Vicki promptly gets a divorce. It doesn't take long for Charley to return west. He and his friends track Vicki to a nightclub where she has taken up with another shady figure. They become involved in a violent brawl. Charley then makes off with Vicki and marries her a third time, to the amazement of his pals. As a gesture of gratitude, Charley sinks millions of dollars into a movie studio where he intends to produce pictures featuring his wife. But while the careers of his buddies take off, Charley and Vicki begin to have children and raise a family. Nothing at the new studio gets under way and Charley goes broke. He angrily blames Vicki, who walks out on him yet again.
Divorced and depressed, a haggard-looking Charley is found by his friends quite a bit later at a nightclub, where he tells them he has recently gone into a promising new line of work: computers. He stares dreamily at the stage where Vicki is performing her act. Charley shows his friends a diamond engagement ring that he has brought with him. Vicki slides it onto her finger.
- Alec Baldwin as Charley Pearl
- Kim Basinger as Vicki Anderson
- Armand Assante as Bugsy
- Paul Reiser as Phil
- Fisher Stevens as Sammy
- Steve Hytner as George
- Peter Dobson as Tony
- Robert Loggia as Lew Horner
- Elisabeth Shue as Adele
There has been speculation that Neil Simon based the character of Vicki on singer Marie McDonald, a '50s performer nicknamed "The Body" who was married to shoe mogul Harry Karl more than once and also reportedly the mistress of Bugsy Siegel.
Charley Pearl's four friends, the comedian, songwriter, singer and baseball manager, are believed to be loosely based on Phil Silvers, Sammy Cahn, Tony Martin, and Leo Durocher, according to AllMovie.com and other sources.
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