If you loved the quirky charm and romantic misadventures of 'Two If by Sea' (1996), you're in for a treat! This article explores 10 similar movies and shows that capture the same blend of humor, romance, and heist antics. Whether you're a fan of offbeat love stories or lighthearted crime capers, these picks will keep you entertained.

Dumb and Dumber (1994)
Description: A road trip comedy featuring two dim-witted friends getting into ridiculous misadventures, with a mix of crude humor and heartwarming camaraderie.
Fact: The film's iconic tuxedo scene was inspired by a real-life incident involving the Farrelly brothers. It was Jim Carrey's first major box office hit.


The Mask (1994)
Description: A zany comedy about a timid man who transforms into a chaotic, cartoonish character, blending physical comedy with a romantic subplot.
Fact: The film's special effects were groundbreaking for its time, blending live-action with animation. It was originally intended to be a horror movie.


Billy Madison (1995)
Description: A goofy, over-the-top comedy about a man-child who must prove himself through a series of absurd challenges, filled with ridiculous humor and a redemption arc.
Fact: The film was Adam Sandler's first leading role in a major motion picture. The script was written in just two weeks.


Tommy Boy (1995)
Description: A buddy comedy featuring a lovable but dim-witted protagonist on a road trip, combining physical comedy with a touching friendship dynamic.
Fact: Chris Farley and David Spade improvised many of their scenes together. The film has since become a cult classic.


Black Sheep (1996)
Description: A comedy about an unlikely duo causing chaos in a political campaign, filled with slapstick humor and absurd situations.
Fact: The film was shot back-to-back with 'Tommy Boy' using the same crew. It was initially less successful but gained a following over time.


Happy Gilmore (1996)
Description: A sports comedy centered around an unconventional athlete who brings chaos and humor to a traditionally serious sport, with a mix of slapstick and heartfelt moments.
Fact: Adam Sandler performed most of his own golf swings in the movie. The film's success helped popularize golf among younger audiences.


Kingpin (1996)
Description: A sports comedy about a washed-up athlete and a naive amateur, blending raunchy humor with a redemption story and quirky characters.
Fact: The film's bowling scenes were choreographed by professional bowlers. It was initially a box office disappointment but later gained a cult following.


The Waterboy (1998)
Description: A comedy featuring an underdog protagonist with a unique talent, blending humor with heartwarming moments and a feel-good resolution.
Fact: The film was initially given an R rating but was edited to secure a PG-13 rating. It was one of the highest-grossing sports comedies of its time.


There's Something About Mary (1998)
Description: A romantic comedy with outrageous humor and a lovable but flawed protagonist, mixing slapstick with a heartfelt love story.
Fact: The film's infamous 'hair gel' scene was almost cut for being too risqué. It became one of the highest-grossing R-rated comedies at the time.


Me, Myself & Irene (2000)
Description: A comedy about a man with a split personality causing chaos in his life, featuring absurd humor and a quirky romance.
Fact: Jim Carrey's dual role required extensive makeup and wardrobe changes. The film's script was inspired by a real-life case of dissociative identity disorder.
