Every Adam Sandler and Drew Barrymore movie, ranked from worst to best


Comedy icon Adam Sandler has teamed up with Drew Barrymore three times to star in romantic comedies, and here’s their ranking, from worst to best.

This is how the films starring Adam sandler and Drew barrymore rank, from worst to best. While Sandler certainly has many detractors, it’s safe to say that his career has been very successful. After his Saturday Night Live unceremoniously executed by dismissal, Sandler wasted no time becoming one of Hollywood’s biggest movie stars, straddling 1990s classics like Billy Madison, Happy Gilmore, and The water boy at the top of the box office. As much criticism that Sandler received for playing similar male-child characters in every movie, audiences really didn’t seem to care too much.

Along with this strategy which worked for Sandler at the time, he also branched out at times, such as when he first showed his considerable dramatic abilities in 2002. Punch drunk love, directed by Paul Thomas Anderson. In 1998, Sandler also starred in The wedding singer, which, despite being a comedy, saw it deviate from Sandler’s standard formula and characterization. Instead of, The wedding singer took the route of romantic comedy and introduced a lovely couple between Sandler and Barrymore.


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Sandler and Barrymore’s chemistry was electric onscreen, and their interaction helped Sandler expand his comedic lineup a bit. The wedding singer was a box office success and also received positive reviews from critics, a big departure from the criticism received by people like Billy Madison. Sandler and Barrymore will later attempt to replicate the formula with that of 2004 50 first dates and 2014 Mixture. Here’s how their three collaborations stack up.

3. Mixed (2014)

A decade later 50 first dates came Mixture, and after two collaborations that became box office hits, Sandler and Barrymore both probably thought they were making a safe bet teaming up for comedy. Frank Coraci, director of The wedding singer, even returned to lead the ship. Sadly, Mixture was a failure, according to most, earning both appalling reviews and an anemic box office. By this point, Sandler had had a less than stellar film series such as Jack and Jill, Go with that, and This is my boy, and had apparently started doing his comedic shtick on autopilot. Sandler and Barrymore still had some chemistry, but MixtureThe storyline, crammed with overused romantic comedy clichés and forced intrigue, gave them little to work on. In addition to being partially located in Africa, Mixture is a very generic exercise, sometimes even boring.

2.50 first dates (2004)

50 first dates lucy and henry

Sandler and Barrymore’s second film collaboration, 50 first dates, was not as good as The wedding singer and doesn’t fare well with reviews. Admittedly, it was still a charming time. Sandler and Barrymore’s chemistry carried things well, even despite a few misguided shenanigans from frequent Sandler cohort, Rob Schneider in a supporting role. What really propelled 50 first dates forward, however, was his central genius vanity, in which Sandler’s Henry was forced to woo Barrymore’s Lucy over and over again after falling in love with her due to a car accident that affected his memory. While there are a few ethical questions that could be raised about the whole situation, 50 first dates wasn’t really a movie that tries to get that deep. It’s just an enjoyable romantic comedy that’s always easy to watch and surprisingly moving.

1. The Wedding Singer (1998)

Adam Sandler Wedding Singer Drew Barrymore

The wedding singer may seem like the obvious choice for the top spot, and it is, but it is for a reason. Commonly regarded as one of the best films of Sandler’s or Barrymore’s career, The wedding singer was a romantic comedy – and one of the best of them – that didn’t really favor one over the other, which bothered many of its contemporaries in the genre. The blossoming romance between Adam sandleris Robbie and Drew barrymore‘s Julia never felt pressured and never failed to be utterly charming. At the same time, the comedy was almost entirely topical, too. This was especially true of Robbie’s hilarious and depressing reaction to her ex-fiancé leaving him at the altar. Robbie and Julia were so nice together it was a shame Wedding singer the sequel never took place.

More: The Happy Ending Of 50 First Dates Is Secretly Really Tragic

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