What is the first name that comes to mind when you think of rom-coms? Meg Ryan? Julia Roberts? Hugh Grant? They’re all fantastic, but there’s another equally distinguished name that tends to get overlooked in the genre: Adam Sandler. 

Though the Sandman has established a reputation for bringing the “-com,” to the movies over the course of his career, he’s also proven he is every bit as capable of pulling off a grand gesture and nailing a meet-cute. So, in honor of Valentine’s Day, I decided to rank Sandler’s rom-coms from worst to best.

Before we dive in, I want to acknowledge a few Adam Sandler movies that you won’t be seeing in this ranking: 

Billy Madison and Happy Gilmore. These are my two favorite Sandler movies and if this was a ranking of his filmography, they’d be right at the top of the list. But, alas, they’re pure comedies. There is a love interest that Sandler’s character ends up with in both but you could easily remove the romantic storyline entirely and not much would change (Little Nicky is in the same category but I anticipate there will be fewer outcries over this one).

Punch Drunk Love. Fantastic movie that first showed us the range of the Sandman as an actor. But while you could make a case for it being a rom-com, I think you’d just be arguing semantics. At its core, PDL is a romantic drama with a few comedic elements sprinkled in there (mainly the Philip Seymour Hoffman storyline). 

Any other favorites missing? It very likely did not meet our criteria. With that out of the way, let’s get to ranking.

Sandler and Drew Barrymore had an impeccable track record up to this point, establishing themselves as rom-com royalty among the likes of Hanks/Ryan and Gere/Roberts. But Blended was a major misfire for the duo, as it feels like the kind of half-baked product that has spurred speculation that Sandler mostly plans his movies around where he can have a fun vacation (more power to him, if that’s the reality). It’s a bizarrely convoluted plot, as Sandler and Barrymore play a widower and divorcee, respectively, who end up on “blended familymoon” (is that a thing?) in Africa despite previously having gone on a blind date that did not go well. Blended is not an outright terrible movie but it’s pretty devoid of any of the charm of the previous Sandler-Barrymore films and both of them seem to be content phoning in their performances and hoping they can rest on their laurels.

Rent it on Prime Video.

Danny (Sandler) pretends to be in a terrible marriage in order to trick women into sleeping with him. Somehow, it’s a strategy that works but his full-proof plan backfires when he meets Palmer (Brooklyn Decker) and actually wants to start a relationship with her. Needing to convince her that he’s getting divorced, he convinces his assistant Katherine (Jennifer Aniston) to pretend to be his soon-to-be-fake-ex-wife. Of course, as the charade continues, Danny and Katherine begin to see each other. Just Go With It is not one of Sandler’s best films by any stretch of the imagination, as it’s filled with unfunny jokes and lazy tropes. But Sandler deserves some credit here, as he is able to keep Danny from being a character you actively root against. And, while the story may leave a lot to be desired, he and Aniston do have solid chemistry that helps the movie avoid being a total disaster.

Watch it on Netflix.

I think Funny People is a pretty underrated movie as a whole but the problem is that it’s sort of two movies clumsily mashed together. For the first half, it’s a  fascinating character study of George Simmons (Sandler), a successful comedian who is forced to reconcile his life and legacy after learning that he’s dying. Then it becomes a Great Gatsby-inspired rom-com with Simmons attempting to reconnect with Laura (Leslie Mann), his “one who got away.” Unfortunately, the first half is significantly better than the second, as the will-they-won’t-they dynamic between the two is a lot less compelling to watch than Simmons realizing that all of his priorities in life have been warped by fame and wealth. You’re never really rooting for Simmons and Laura to get together because the relationship you really find yourself invested in by the end is Simmons and his for-hire joke writer Ira (Seth Rogen), so much so that the movie ends with them getting back together. Ultimately, this feels like a classic example of Judd Apatow making his movies 20-30 minutes too long. 

Rent it on Prime Video.

Sonny is the classic man-child archetype that Sandler played for most of his early career. He’s a 30-something with no real direction in life who gets dumped by his girlfriend for his lack of ambition. But that all changes when a five-year-old named Julian (Dylan and Cole Sprouse) is dropped at his apartment and he begins raising him. So far, this doesn’t really sound like a rom-com but Sonny’s pseudo-fatherhood experience gives him purpose and forces him to grow up. And as he matures, he meets Layla (Joey Lauren Adams), an attorney who would have had zero interest in Sonny if she had met him at the beginning of the movie. But through Sonny’s personal growth, he becomes the type of guy who isn’t afraid of being in a healthy, committed relationship. And while Sonny and Julian’s father-son relationship inevitably comes to an end, it was an essential part of helping him find love.

Rent it on Prime Video.

An argument could be made that Mr. Deeds is more of a comedy than a rom-com but I think it falls into the latter category for one big reason: Without the romance between Longfellow Deeds (Sandler) and reporter Babe Bennett (Winona Ryder), not much actually happens in this movie other than the titular Mr. Deeds being amazed by how rich he suddenly is after inheriting the fortune of a billionaire granduncle(?) he didn’t even know he had. The relationship between Deeds and Longfellow is central to the story and includes all of the staples of the rom-com genre, including someone lying about who they are, the other person discovering the lie just as the two are falling for each other, and a reconciliation caused by a grand gesture that redeems the person who was lying. Ryder actually gets to do more than just fall for Adam Sandler, which is not the case in several of his comedies. Plus, the failed attempt at a meet-cute in the form of a staged mugging remains hilarious.

Watch it on Peacock.

How do you convince someone you’re their soulmate when every time they wake up, they don’t remember who you are? That’s the central question at the heart of 50 First Dates, as proud bachelor Henry (Sandler) ends up falling for Lucy (Barrymore), who has a rare form of amnesia where she can’t remember anything that happened the day before. This is a difficult premise for a rom-com and in lesser hands, it’s not hard to imagine it wandering into creepy territory. But instead, you find yourself rooting for this unusual romance and seeing the lengths that Henry will go to in order to make things work with Lucy feels authentic and sweet, in no small part thanks to an earnest and heartfelt performance from Sandler.

Rent it on Prime Video.

If you want proof that Adam Sandler could have made a career as a leading man in rom-coms, look no further. Up to this point, Sandler had mastered the art of playing idiot goofballs but here, he showed his range by wearing his tender heart on his sleeve. The plot is simple but filled with nearly every staple of the genre: Robbie (Sandler) is a wedding singer who meets and begins falling for Julia (Barrymore), a waitress who is engaged to a total a-hole, shortly after he is stood up at the altar on the day of his wedding. It all culminates in a genuinely heart-warming grand gesture that still makes me cry every time I watch it. What really makes this movie an undeniable entry into the Rom-Com Hall of Fame is the dynamite chemistry between Sandler and Barrymore, as you really do feel like you’re watching two people fall in love right in front of you. This movie is not just Sandler’s best rom-com (by a pretty wide margin), it’s one of the best rom-coms ever made.

Watch it on HBO Max.