Adam Sandler rose to fame in the 1990s when he appeared as a cast member on NBC’s iconic Saturday Night Live sketch comedy show. Sandler spent five years with Saturday Night Live where he refined his comedy, became known for his comedic songs, and even forged a lifelong friendship with several of the show’s cast members.
Upon leaving the show, Sandler ventured into the world of feature films, where he often played goofy characters. Shortly after, he founded his own production company where he had control over the movies and shows he made and starred in. While Sandler is known for his comedies, he also became a surprising romantic-comedy lead. Several decades into his career, Sandler continues to appear in romantic comedies and woo the hearts of millions of fans around the world.
Mr. Deeds (2002) – 5.8
Mr. Deeds might not be thought of as a traditional romantic comedy, but it definitely has some of the right elements. The movie, which is a remake of the 1936 movie based on a short story, stars Sandler as Longfellow Deeds. Deeds is the nephew of a billionaire and he leaves his entire greeting card empire to Deeds when he dies. The news of the inheritance sparks Babe Bennet (Winona Ryder) to track down Deeds to write a story about him.
After Deeds “rescues” her upon their first meeting, Babe lies about her identity and the two quickly begin to fall for each other. In the end, the two end up helping each other before they go off to live happily ever after.
Murder Mystery (2019) – 6.0
Though Sandler’s movies tend to be high-earning at the box office, he took a deal with Netflix to create a host of original movies for the streaming service. Murder Mystery was one of those movies. And though it might not feature the romantic grand gestures that rom-coms are known for, it does have that Sandler rom-com vibe to it.
Sandler plays Nick Spitz, an NYPD officer who takes his wife, Audrey (Jennifer Aniston), on a once in the lifetime European vacation on a billionaire’s yacht to reignite their marriage. However, things take a turn when the two get wrapped up in a murder mystery after the billionaire is murdered.
Billy Madison (1995) – 6.4
One of Sandler’s first movies after leaving Saturday Night Live was Billy Madison. Though the comedy movie received mixed reviews, it was a commercial success. It also was the gateway to Sandler becoming an iconic rom-com lead.
The movie centers on Billy Madison, a dumb 20-something heir who is forced to go back to school if he wants to inherit his father’s company. While back in school, Billy ends up falling for one of his teachers, and two must navigate their complex relationship.
Big Daddy (1999) – 6.4
Big Daddy might be one of Sandler’s most heartfelt comedies of all time. It premiered in the number one spot at the box office and became the seventh highest-grossing movie of the year and Sandler’s most profitable until 2015. While it’s not a traditional rom-com, there is a strong romance at its center, making for tons of adorable moments in the movie.
The story centers on Sonny, a 32-year-old slacker who refuses to get his life on the track, causing his girlfriend to dump him. After a young child is dropped on his doorstep for his out-of-town roommate, Sonny decides to adopt the young boy in the hopes of winning his ex back. While that plan doesn’t work, Sonny does end up bonding with another woman who quickly becomes his best friend and love interest.
Just Go With It (2011) – 6.4
Just Go With It is one of Sander’s most underrated movies, and certainly his most underrated romantic comedy. A remake of a 1969 movie, it premiered in 2011 and though it was commercially successful, it was panned by critics and even nominated for two Golden Raspberry Awards.
The movie stars Sandler as Danny, a plastic surgeon who was left at the altar when he was in his 20s. In the present, he uses his wedding ring to pick up women who feel sorry for him when he says he’s unhappy in his marriage. His plan backfires when he finally meets the one forcing him to rope in his assistant, Katherine (Jennifer Aniston), and her kids, to pretend to be his fake family.
Blended (2014) – 6.5
Sandler and Drew Barrymore have a strong history of appearing opposite each other in romantic comedies and Blended marks their most recent pair up. It, once again, was nominated for Golden Raspberry Awards despite being profitable at the box office.
The movie follows Sandler and Barrymore who both play single parents raising their children. The two are set up on a blind date that ends with them agreeing to never see each other again. However, the universe has other plans for them when both of their families end up at the same African safari resort where they are forced to spend time together.
50 First Dates (2004) – 6.8
Sandler and Barrymore teamed up for the second time in 2004 to bring to life the underrated rom-com, 50 First Dates. It’s one of few Sandler movies to actually receive generally positive reviews from critics.
The movie follows Henry (Sandler) a womanizer who falls for Lucy (Barrymore), a local art teacher. They spend a perfect first day together but when Henry approaches her a day later, she has no idea who he is. It’s then that Henry learns that Lucy is unable to make new memories due to a horrific auto accident that now has her living the same day over and over again.
The Wedding Singer (1998) – 6.9
Sandler’s first real romantic comedy movie was 1998’s The Wedding Singer, which he starred in opposite Drew Barrymore. To this day, it is one of Sandler’s most popular and well-reviewed movies of all time and even earned a Broadway adaptation.
Set in 1985, the movie follows Robbie Hart (Sandler), a wedding singer who is left at the altar at his own wedding. Disheartened by his breakup, Robbie has a hard time finding the magic in weddings until he meets Julia (Barrymore), a young woman who wants his help planning her own wedding. As the two get to know each other, they begin to fall for each other and the movie culminates in one of the best romantic grand gestures in rom-com history.
Punch-Drunk Love (2002) – 7.3
Punch-Drunk Love may be considered a romantic comedy, but it also has strong dramatic elements to it too. Unlike most of Sandler’s movies, this one was well-reviewed by critics and yet it was considered a box office flop.
The movie centers on Barry (Sandler) a timid but ill-tempered bathroom supply business owner who meets and begins to fall for one of his sister’s co-workers. The two start a friendship and when Barry follows her to Hawaii, they begin to fall in love. However, his past comes to haunt him when he is hunted down by four brothers who want him to pay for a phone sex line he called when he was lonely at the beginning of the movie.
