Movies like The Ladies Man

In The Waterboy, a socially inept protagonist finds success and self-esteem through an unexpected talent. Viewers who took pleasure in watching Leon Phelps' overconfident ineptitude in The Ladies Man will likely find humor in the assured, yet misplaced self-confidence of Adam Sandler's character.

A Night at the Roxbury features the misadventures of two socially awkward brothers as they attempt to open their own club. Fans of The Ladies Man will enjoy the nightclub setting and the comedic misunderstandings that come from the protagonists' pursuit of romantic connections, paralleling Leon Phelps' clumsy charms.

Like The Ladies Man, Deuce Bigalow: Male Gigolo turns the tables on gender stereotypes with its plot about an accidental gigolo. The awkward, yet heartfelt attempts at romance and the quirky array of characters he encounters will resonate with anyone who enjoyed the unconventional love story in The Ladies Man.

Superstar, which spins off another popular Saturday Night Live character, Mary Katherine Gallagher, into her own film, captures a similar comedic style. Those who appreciated the quirky humor and offbeat romance of The Ladies Man will find more to love in this tale of a Catholic schoolgirl's quest to achieve her dreams.

The Love Guru centers around an eccentric self-help guru who attempts to reunite a star hockey player with his wife. With its blend of ridiculous advice, slapstick, and romance, fans of The Ladies Man's comedic take on love and relationships will likely enjoy this romp as well.

B.A.P.S. focuses on two sassy friends from Georgia who go to Los Angeles to audition for a music video, only to be mistaken for heiresses. Its outlandish humor and the protagonists' navigation through high society will appeal to The Ladies Man audience looking for more outrageous character-driven comedy.

Booty Call is a raunchy romantic comedy that follows the escapades of two friends looking to take their relationships to the next level. The wild, comedic sexcapades and hilarious situations make it a natural follow-up for fans of The Ladies Man's less than smooth romantic adventures.