The Ladies Man

After his raunchy radio persona costs him his Chicago gig, Leon Phelps finds himself out of work and scrambling for options. His loyal producer Julie sticks by him, hoping to keep things steady. Then a letter arrives from a former lover promising a fortune, and Leon realizes the mystery woman could change his life if he identifies who she is. The prospect of wealth becomes a catalyst for a city-spanning scramble as Leon and Julie navigate a maze of flirtations, fashionably loud parties, and shady schemes. They chase clues, dodge rivals, and test their friendship as both of them weigh loyalty against the lure of easy money, without spoiling what lies ahead.

Directed by Reginald Hudlin, The Ladies Man came out in 2000. It adapts the Saturday Night Live character Leon Phelps created by Tim Meadows and collaborators into a feature with a sharper comic edge and a bigger Chicago setting.

The film drew mixed reviews and carries a modest 5.3 out of 10 score from audiences. It looks at fame and male fantasies through raunchy humor and flirtatious misadventures, while also poking at loyalty, friendship, and the temptations that come with sudden wealth.

Culturally the film has a limited footprint outside fans of Tim Meadows. It reflects a specific era when SNL sketches were spun into feature comedies. Some jokes feel dated, but the movie remains a snapshot of early 2000s noted pop culture humor.

Awards: The film did not secure major nominations or wins, and it did not feature in major ceremonies. In the end, critics who watched it noted Tim Meadows' performance but the project failed to become a contender during awards seasons.