playboy

American  

[pley-boi] / ˈpleɪˌbɔɪ /

noun

• playboys
  plural

1. a man who pursues a life of pleasure without responsibility or attachments, especially one who is of comfortable means.

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playboy British  

/ ˈpleɪˌbɔɪ /

noun

1. a man, esp one of private means, who devotes himself to the pleasures of nightclubs, expensive holiday resorts, female company, etc

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Other Word Forms

Noun Inflected Forms

• playboys
  plural

Etymology

Origin of playboy

First recorded in 1620–30; play + boy

Example Sentences

See Examples For:

playboy playboys

The 41-year-old royal misfit has long struggled with the monarchy's strictures, shaking off the angry young man and "playboy prince" tags only to find himself at loggerheads with his closest relatives.

From Barron's ● Aug. 23, 2026

Before that date he was “millionaire playboy Jeffrey Epstein.”

From The Wall Street Journal ● Nov. 20, 2025

Oh yeah, and in 1992 Donald Trump was a playboy tycoon in his mid-40s, at the peak of his tabloid celebrity.

From Salon ● Aug. 31, 2025

It is about a con-man taking on the identity of a wealthy playboy.

From BBC ● Aug. 8, 2025

You’re a failure, a playboy, a racetrack tout.”

From "A Confederacy of Dunces" by John Kennedy Toole

Paul was “one of the most gregarious playboys in New York City,” according to biographer Frank Brady, author of “The Publisher,” and Paul and William Randolph Hearst were regulars at New York nightclubs.

From The Wall Street Journal ● Apr. 5, 2026

One wonders what he really thought about the pampered, preening, multimillionaire playboys of the contemporary global game, who change hairstyles weekly and win world championships sparingly.

From Los Angeles Times ● Dec. 29, 2022

Until his social media ban, Tate was operating something called Hustler University, which promised, for $49 a month, to turn his audience into rich playboys, as he presents himself to be.

From Salon ● Aug. 23, 2022

He spent the postwar years in Paris, befriending Prince Aly Khan and other jet-setting playboys who frequented casinos.

From Washington Post ● Jan. 11, 2022

He worships the vuvv playboys he works for.

From "Landscape with Invisible Hand" by M.T. Anderson