Every Adam Sandler & Drew Barrymore Movie, Ranked From Worst to Best

Adam Sandler and Drew Barrymore movies are ranked from worst to greatest. Despite his many critics, Sandler’s career has been extremely successful. After his tenure on Saturday Night Live was abruptly interrupted by fire, Sandler pounced on the opportunity to become one of Hollywood’s biggest performers, riding the success of 1990s blockbusters like Billy Madison, Happy Gilmore, and The Waterboy to stardom. Sandler received a lot of flak for portraying man-children in each of his films, but moviegoers didn’t seem to mind.

As well as that method worked for Sandler back then, he did break out at times, such as in 2002’s Punch-Drunk Love, directed by Paul Thomas Anderson, in which he showed off his enormous dramatic ability for the first time. Even though The Wedding Singer was a comedy in 1998, Sandler deviated from the typical Sandler formula and personality in this film. Rather, Sandler and Barrymore’s chemistry in The Wedding Singer made it a sweet romantic comedy.

With their on-screen connection, Sandler and Barrymore were able to stretch their humorous boundaries a bit. This marked a marked improvement over the critical thrashing that films like Billy Madison experienced when they were released, as The Wedding Singer was both a box office success and a critical success. Afterward, Sandler and Barrymore attempted to repeat the concept with 50 First Dates and Blended in 2004 and 2014. As you can see, here are the results of their three previous partnerships.

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3. Blended (2014)

Blended was released a decade after 50 First Dates, and both Sandler and Barrymore undoubtedly thought they were making a safe bet by re-teaming for the comedy after two successful collaborations. Even the director of The Wedding Singer, Frank Coraci, is back at the helm. Unfortunately, Blended was widely seen as a flop, garnering negative reviews and disappointing box office results. Since his previous flicks like Jack and Jill and That’s My Boy and the underwhelming “Just Go With It,” Sandler had gotten into the habit of delivering his comedy act on autopilot. Sandler and Barrymore still had chemistry, but the writing for Blended was so full of tired romantic comedy tropes and forced plot twists that the actors had no room to express themselves. Blended is, other than the fact that it takes place in part in Africa, a very generic and, at times, uninteresting exercise.

2. 50 First Dates (2004)

In 50 First Dates, Sandler and Barrymore collaborated for the first time since The Wedding Singer, although critics didn’t like it as much. There is no denying that it was a beautiful period. With the help of regular Sandler co-star, Rob Schneider’s misguided antics in a supporting role, the chemistry between Sandler and Barrymore kept the movie moving along well. The brilliant underlying idea of 50 First Dates was that Henry, played by Sandler, was compelled to court Lucy, played by Drew Barrymore, repeatedly after falling in love with her due to a car accident that impaired her memory. A few ethical problems may be raised about the situation, but 50 First Dates isn’t a film that aims to be that serious. In other words, it’s a lighthearted romantic comedy that is unexpectedly poignant despite its simplicity.

Drew Barrymore and Adam Sandler Movies
Drew Barrymore and Adam Sandler Movies

1. The Wedding Singer (1998)

The Wedding Singer is the most obvious pick, and it is, but there is a good reason for that. One of the best romantic comedies ever made, The Wedding Singer didn’t favor either Sandler or Barrymore, which handicapped many of its competitors in the same genre. Never once did the romance between Robbie (Adam Sandler), played by Adam Sandler, and Julia (Drew Barrymore), feel forced. The comedy, on the other hand, was nearly flawless. In Robbie’s case, this was especially true, as his ex-fiancee left him at the altar. It was a shame that Robbie and Julia didn’t have a Wedding Singer sequel.

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