Summary

  • The chemistry between Adam Sandler and Drew Barrymore in their movie collaborations is electric, resulting in successful box office hits and positive critical reviews.
  • Despite some setbacks in their careers, such as Sandler's string of less-than-stellar films, their partnership still manages to shine through and captivate audiences.
  • Fans can look forward to a potential new collaboration between Sandler and Barrymore, as they actively search for a new project that showcases their chemistry while offering something fresh and intriguing.

The Adam Sandler and Drew Barrymore movies ranked worst to best captures, at both ends of the scale, one of the most lucrative yet underrated comedic partnerships in Hollywood. Adam Sandler certainly has many detractors, but the box office proves his career has been highly successful. After Adam Sandler was unceremoniously fired from Saturday Night Live, he wasted no time becoming one of the biggest movie stars in Hollywood, starring in 1990s classics like Billy Madison, Happy Gilmore, and The Waterboy to the top of the box office. Barrymore was a child star going back to E.T. The Extra-terrestrial before her comeback as an adult with Scream.

Adam Sandler and Drew Barrymore's chemistry is electric onscreen, and their interplay helped Sandler broaden his comedic range while tapping into Barrymore's kind-hearted good-girl image that defined the last few decades of her career. The Wedding Singer was a box office smash that received positive critical reviews, a big change from the critical thrashing received by the likes of Billy Madison. Adam Sandler and Drew Barrymore later attempted to replicate the formula with 2004's 50 First Dates and 2014's Blended.

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3 Blended (2014)

  • Stream on Max

After two collaborations that were box office hits, Sandler and Barrymore probably thought they were making a safe bet by re-teaming for Blended. Frank Coraci, director of The Wedding Singer, even returned to direct the 2014 movie. The film starred Adam Sandler and Drew Barrymore as single parents who, following a bad blind date with each other, wind up staying at the same resort with their respective kids. Unfortunately, Blended didn't capture the same success as those earlier movies. Along with earning the worst reviews of the three Adam Sandler and Drew Barrymore movies, Blended was also a disappointment at the box office.

By 2014, Sandler had had a string of less-than-stellar films such as Jack and Jill, Just Go With It, and That's My Boy, and he had seemingly begun performing his comedic shtick on autopilot — before moving to Netflix in the late 2010s reignited Sandler's credibility in the eyes of many with solid entries like 2022's Hustle. However, as far as Adam Sandler and Drew Barrymore movies go, the worst still had some chemistry. Sadly Blended's script, packed with overused romantic comedy clichés and forced plot contrivances, gave them little to work with. Outside of being partially set in Africa, Blended is a highly generic and often boring exercise.

2 50 First Dates (2004)

  • Stream on Hulu

Adam Sandler and Drew Barrymore's second movie collaboration, 50 First Dates, wasn't quite as good as The Wedding Singer and didn't fare well with critics. However, it did seem to charm audiences with the return of their winning chemistry. Adam Sandler and Drew Barrymore's work together carried things well, even despite some ill-advised shenanigans from Adam Sandler's friend and frequent collaborator Rob Schneider in a supporting role.

What really propelled 50 First Dates forward, though, was its genius central conceit, in which Sandler's Henry is forced to court Barrymore's Lucy over and over again after falling for her, due to a car accident that affected her memory. While there were a few ethical questions that could be raised about the whole situation, 50 First Dates isn't really a movie that tries to be that deep. 50 First Dates is just an enjoyable romantic comedy that's still an easy watch and surprisingly emotional.

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1 The Wedding Singer (1998)

  • Stream on Prime Video

The Wedding Singer may seem like the obvious choice for the best Adam Sandler and Drew Barrymore movie — and it is, but that's because its place at the top is hard to argue against. The Wedding Singer is Sandler's most overlooked movie and is commonly considered one of the best of Barrymore's career, and it's one of the best in the romantic comedy genre. The movie perfectly walks the tightrope between heartfelt drama and out-and-out humor — a feat that helped it stand out among its contemporaries in the genre.

The blossoming romance between Adam Sandler's Robbie and Drew Barrymore's Julia never felt forced and never failed to be utterly charming. At the same time, the comedy was almost entirely on-point too. This was especially true for Robbie's hilariously depressing reaction to his prior fiancé leaving him at the altar. Robbie and Julia were so likable together that it was a shame a Wedding Singer sequel never happened. As it stands, the 1998 movie is the best Adam Sandler and Drew Barrymore movie, and The Wedding Singer deserves more from Sandler fans.

Why Barrymore And Sandler Are A Pairing For The Ages

Adam Sandler singing to Drew Barrymore in 50 First Dates

Just as Adam Sandler and Jennifer Aniston reunite to lead the cast of Murder Mystery 2 is welcomed because it's known how well the two play off each other on screen, Barrymore is an actor who brings out the best in Sandler. As with many iconic and repeated Hollywood pairings, Drew Barrymore and Adam Sandler work well together onscreen because they also get along off-screen. Both actors often bring plenty of charm, lighthearted humor, and authenticity to their roles, which makes Robbie and Julia, Henry and Lucy, and even Jim and Lauren well-matched pairs.

Even more importantly, every Adam Sandler and Drew Barrymore movie benefits from the fact that the two are good friends, which makes their chemistry flow effortlessly even though not all of their collaborations have been financial successes. As with the likes of Johnny Depp and Tim Burton, some Hollywood collaborations are simply so fulfilling for both people that they're destined to be repeated over and over. Given that there are three Adam Sandler and Drew Barrymore movies that set them up as a romantic pair, the actors clearly love working with each other.

Barrymore & Sandler Have Teased A New Collaboration

Drew Barrymore and Adam Sandler in robes in Blended

It has been almost a decade since Blended, so it seems like time for another Adam Sandler and Drew Barrymore movie. Thankfully, the duo teaming up once again seems like an inevitability with Barrymore and Sandler actively looking for a new project. Barrymore herself confirmed this saying "Maybe not be redundant of something we've done in the past, but not try to prove we're doing something different just to prove it." Not only is it exciting that the two are planning on working together again, but the prospect of it being something new is very intriguing.

Sandler continues to prove himself as a talented actor with his acclaimed role in Hustle and the exciting upcoming Sandler movies like Spaceman and another collaboration with Uncut Gems directors the Safdie Brothers. Like Sandler, Barrymore is an actor whose talents are sometimes underrated and who could use a great project to remind people of her versatility. While Barrymore also pitched a Three's Company reboot with Sandler and Aniston (via Vulture), something completely new for the stars would be the ideal next Adam Sandler and Drew Barrymore project.

The Adam Sandler Drew Barrymore Is Their Best Pairing

Drew Barrymore and Adam Sandler eating waffles in 50 First Dates

Adam Sandler has a number of long-time working relationships with other big-name actors. The actor often works with the same comedy actors, such as Rob Schneider, Henry Winkler, and so many others. That's no different with his romantic pairings too, as Sandler has worked with Barrymore three times, and Sandler and Jennifer Aniston have four movies together. Even Kevin James could be considered one of Sandler's frequent romantic leads based on I Now Pronounce You Chuck & Larry, which sees the two get married for insurance purposes. However, there's no better pairing than Adam Sandler and Drew Barrymore.

Adam Sandler and Drew Barrymore totally bring out the best in each other. While Aniston and Sandler are always entertaining together, Aniston often plays the straight character who always gets angry at Sandler's character for doing something stupid. On the other hand, Barrymore is often just as goofy as Sandler in their movies together. In 50 First Dates, Lucy has a fiery personality and even beats Rob Schneider's character with a golf club when he acts creepy. Barrymore plays unpredictable characters, and it's always fun to watch Sandler play off that performance. That's why Adam Sandler and Drew Barrymore make an iconic pairing.

Source: Vulture.