Adam Sandler is a man of many talents. While his dramatic skills have been snubbed time and time again by the Academy Awards, his stature in comedy is rarely questioned. Although he started his career as a more zany comedy star, his romcoms are some of his most popular and successful projects.
From the sun-soaked beaches of 50 First Dates to the 80’s soaked chaos of The Wedding Singer, Sandler has built a romcom filmography that spans decades and defies easy categorization. His leading-man charm is equal parts goofy and genuine. With that, he has a way of making even the most absurd premises feel surprisingly heartfelt. So, here’s our ranking of every Adam Sandler romcom movie.
6. Mr. Deeds (2002)
Mr. Deeds is perhaps the campiest of Adam Sandler romcom movies. It’s silly, supporting players overact, and the subplots are eccentric and over-the-top. However, there’s some tremendous heart at its core. The plot follows Longfellow Deeds (Sandler), a small-town pizzeria owner who inherits a controlling stake in a media conglomerate and leaves his quaint home for the first time in his life. As he begins to operate the business his own way, the tabloids become obsessed with him. This is where reporter Babe (Winona Ryder) comes in to get close to him in the hopes of doing an exposé.
As can be expected, the unlikely duo end up falling for each other, thus thrusting the movie into formulaic territory. Yet alongside appeasing to typical romcom fans, Mr. Deeds elevates with its ability to subvert other parts of the formula. Doubling as a fish-out-of-water comedy, we watch as Deeds gets in over his head but dishes out life lessons along the way. Instead of being a broken or damaged character who needs the help of others to change, the lid is flipped and Deeds sets out to change those around him by teaching them to enjoy the small things in life and unlock their empathy for other people.
5. Just Go With It (2011)
Just Go With It does follow the flawed main character formula as Adam Sandler takes on the role of the womanizing plastic surgeon Danny Maccabee. After a failed engagement scarred him early in life, Danny has come up with a defence mechanism approach to dating, typically built on white lies that help him avoid commitment. However, when one of his tell-tales spirals out of control, he enlists the help of his assistant to stop it from spiralling out of control and keep the woman of his dreams.
Jennifer Aniston stars as Danny’s receptionist Katherine, a single mother who agrees to pose as his ex-wife so he can secure his new relationship. With the whole gang heading on a vacation to Hawaii, the web of lies becomes messy and inflated when Danny and Katherine begin to develop feelings for one another. While totally trope heavy, Just Go With It is a crowd pleaser. The romantic tension is almost secondary to the chaos of keeping the facade going. The plot mechanics do a lot of the heavy lifting over genuine chemistry, but there’s an important message at its core of how a lie can quickly spiral and damage others.
4. Blended (2014)
When Blended was released in 2014, it represented a major event in romcom cinema, pairing together Adam Sandler and Drew Barrymore for the third time. After the success of their prior comedy-centric movies, Blended leans more towards drama, focusing on two single parents dealing with the aftermath of loss. The plot follows Jim and Lauren, who after an unsuccessful blind date, find themselves stuck together at a resort for families. As their respective kids benefit from the burgeoning relationship, their attraction grows as they slowly let down their steel guards.
More grounded and simple than their two other collaborations, Blended allows both Sandler and Barrymore to dig deep emotionally, with comedy being a side dish rather than the main course. This heartfelt flick garners its place through earned emotional warmth rather than sharp writing. While it is another mismatched couple story, the blended family angle warms our hearts as we see two broken families slowly becoming whole. It’s sentimental and broad, but the sincerity is hard to argue with.
3. 50 First Dates (2004)
At the time of its release, 50 First Dates was strikingly different from other Adam Sandler movies. Although he had already dabbled in romcoms, this film saw him strip away the hostility and gross-out humor he had become famous for. Most notable, his character was warm and caring, a far cry from his anger-soaked turns in films like Happy Gilmore and Punch-Drunk Love.
Heavily inspired by the story of Michelle Philpots, a British woman who developed a daily memory reset after accidents in 1985 and 1990, Peter Segal‘s high-concept romcom follows Henry Roth (Sandler), a man afraid of commitment until he meets the beautiful Lucy (Barrymore). However, when he arrives for a second date and she doesn’t recall ever meeting him, he learns of her plight. Instead of giving up, he sets out to win her heart all over again every single day. While supporting stars like Sean Astin and Rob Schneider bring forth the manic energy and zaniness, the true heart of the picture comes from the deeply emotional and dedicated love story. Today, 50 First Dates is looked upon as a timeless classic in the romcom realm.
2. Punch-Drunk Love (2002)
With Paul Thomas Anderson behind the wheel, Punch-Drunk Love was never going to be your standard romcom. The story focuses on Barry Egan (Sandler), a socially frustrated man who struggles to connect with other people, including his own family. When he calls a phone-sex line to curb his loneliness, he is blackmailed and finds his burgeoning romance with the mysterious Lena (Emily Watson) put at major risk.
Although difficult to watch at times due to the awkwardness, the romance is tender and real. Anderson ditched the standard fairy tale narrative to deliver a much more realistic take on love, something that is rarely straight-forward. While this brings subtle shades of comedy, the rest comes from the absurdity of the backstories, with everything surrounding the unlikely romance being suffocating and bizarre. It’s the only entry on this list that treats Sandler as a purely dramatic instrument, and as his first ever dramatic role, it might actually be his best rendition to date.
1. The Wedding Singer (1998)
The Wedding Singer was a pivotal moment in Adam Sandler’s career, transforming him from a goofy comedian to a versatile talent. What stands out most is his ability to exude natural charm, stripping away over-the-top character traits seen in films like Happy Gilmore and Billy Madison to deliver something multidimensional. The story focuses on Robbie Hart, a heart-broken wedding singer who falls for waitress Julia (Barrymore), who’s engaged to the controlling and sleazy Glenn (Matthew Glave).
While the plot indeed follows the classic “wrong partners, right timing” trope, the execution is what elevates it. Robbie isn’t just a caricature – he’s a man dealing with genuine heartbreak and existential crisis, making his eventual connection with Julia feel earned rather than scripted. The Wedding Singer manages to keep the “Sandler-isms” comedy fanatics love (like the occasional outburst or the hilarious Billy Idol cameo) while maintaining a core of sincerity. It doesn’t rely on mean-spirited humor to get a laugh, choosing instead to lean into the sweetness of its central romance. The result is a definitive romcom of the 90s, standing the test of time today, still performing well on streaming charts.
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