Perennial funny man Adam Sandler has entertained us for years with slapstick comedies and iconic characters. His movies don’t always hit, but you can’t deny that they were a big part of the 2000s comedy scene.

Interestingly enough, the comedian has also dabbled in a pretty good number of romantic comedies. They’ll make you laugh and warm your heart, so if you’re looking to relive the feel-good butterflies of the best Adam Sandler romcoms, you should check these films out.

The Wedding Singer (1998)

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Image from New Line Cinema

It’s an Adam Sandler/Drew Barrymore classic! The film marked the first of the duo’s iconic pairing, showing Sandler as a depressed wedding singer and Barrymore as a waitress and bride-to-be. The two strike up a warm friendship that eventually gave us the sweet masterpiece that was “Grow Old With You.”

Punch-Drunk Love (2002)

Image from Sony Pictures

In Punch-Drunk Love, we follow the story of a loner named Barry who finds love in the arms of his sister’s co-worker, played by Emily Blunt. The film was lauded for Sandler’s deeper portrayal of a man with social anxiety, as well as for the more unique, humorous, and touching tone of the plot. Fun fact: it was even nominated for the Palm d’Or that year!

50 First Dates (2004)

Image from Columbia Pictures

The perfect pair reunite again for this early 2000s comedy, but this time, Sandler is a playboy marine veterinarian who chance encounters Barrymore’s character, an art teacher who experiences memory loss at the beginning of every day. What results is a hilarious, heartwarming tale of a man in love trying to woo the girl of his dreams against the backdrop of the beautiful Hawaii. This is arguably one of Sandler’s better romcoms, so give it a watch!

Spanglish (2004)

Image from Columbia Pictures

More of a comedy film than a romcom, Spanglish depicts the dysfunctional workings of a modern American family. Here, Sandler is an easygoing father of two, married to an uptight and domineering wife (played by Téa Leoni). The family, however, experiences a change in pace when they welcome in a Spanish-speaking housekeeper and her daughter.

Murder Mystery (2019)

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Image from Happy Madison Productions

Funny, entertaining, and the most popular Netflix title in 2019, Murder Mystery saw the veteran team of Adam Sandler and Jennifer Aniston (they did Just Go With It together 8 years prior) take on the roles of a married couple who get tangled in a mysterious murder aboard a yacht. The “whodunit?” type movie raked in 30.9M account views within just three days of its release, showing off the supreme comedic power of the Sandler-Aniston tandem.

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