20 Years of ‘50 First Dates’ — Ranking Adam Sandler and Drew Barrymore Films

When we think of iconic romantic comedy duos, Adam Sandler and Drew Barrymore might be the first to come to mind. 20 years ago on February 13th, 2004, they starred in 50 First Dates, one of the most unforgettable films (even if Drew’s Lucy can’t remember it). It’s a charming love story between Adam’s Henry and Lucy, whose short-term memory loss never conquers their chemistry.

As the second film in a series of three starring Adam and Drew, 50 First Dates has also inspired actors to work together in multiple films. Adam also has a series of three films with Jennifer Aniston, but he’s not the only one who repeats his scene partners. Ryan Gosling and Emma Stone have starred in three films. Eugene Levy and Catherine O’Hara played partners in three projects. Even Keanu Reeves and Winona Ryder have also joined in on the fun. And we can’t forget Kristen Stewart and Jesse Eisenberg. But for now, we’re ranking Adam and Drew’s films from worst to best.

3. ‘Blended’ (2014)

When it was announced that Drew and Adam would reprise their classic pairing in this 2014 Netflix film, fans were overjoyed. It seemed like a precedent that perhaps, in another ten years, they’d do it again. That leads us to 2024! But while both Adam and Drew have mentioned looking for another project to do, there doesn’t seem to be anything on the docket, which makes Blended just slightly less promising than we had hoped.

The film itself is not up to par with Drew and Adam’s first two, which automatically makes it a disappointment. Even though it has decent jokes, it’s impossible not to compare it with 50 First Dates and The Wedding Singer. In all fairness, it’s way harder to make a rom-com that’s not contrived in 2014 than it was in 1998. But despite the star power behind Blended, the story felt forced and predictable at the same time, so it’s easily the worst of the Adam and Drew films.

2. ‘50 First Dates’ (2004)

50 First Dates follows Adam’s Henry after he meets Drew’s Lucy in a restaurant. Lucy is opinionated and charming, and their characters’ immediate chemistry is impossible not to root for. However, Henry quickly learns that Lucy suffers from short-term memory loss due to a tragic accident. On top of that, Lucy’s family is very protective of her and thinks it’s best for Henry to just move on. But these unique obstacles are weak against Henry’s determination. 

Throughout the past 20 years, 50 First Dates has set a standard for rom-coms by proving that love stories can be told through a male perspective and still be beloved by all. With Adam’s trademark humor, 50 First Dates combines slapstick comedy with an emotional undertone as Henry has to find a unique solution to a unique problem to win Lucy over every single day. 

In fact, 50 First Dates may have been inspired by the story of Michelle Philpots, who luckily met her husband, Ian, before the accident that caused her memory loss. But Michelle and Ian got married in 1997, years after her symptoms started, so he reminds her of their wedding everyday with a photo album. This fact makes 50 First Dates all the more romantic. However, some of the jokes, especially those with Rob Schneider, are a bit cringe today, so it still falls short of its predecessor.

1. ‘The Wedding Singer’ (1998)

The Wedding Singer was Adam and Drew’s first film together, and it will always be a crowd-pleaser. If we think about their movies like the phases of a relationship, The Wedding Singer was easily the honeymoon phase. Every moment is exciting and electric. To this day, Adam credits Drew with making him seem desirable as a romantic lead. The Wedding Singer is also an early example of a comedically goofy man branching out into a different type of role.

Adam’s Robbie was recently dumped by his evil ex, but ironically, he’s a wedding singer. While working a particularly depressing wedding, Robbie meets Drew’s Julia, who is in a not-so-great relationship. Robbie and Julia help each other through these challenges as friends, but it all culminates with Robbie’s romantic gesture when he plays a legitimately good song to win over Lucy on an airplane. It takes the cake as the best film because, despite how great 50 First Dates was, every moment in The Wedding Singer has value. And it’s impossible not to fall in love with Adam and Drew.

The Drew Barrymore & Adam Sandler Movies That Never Were

While there are only three Drew and Adam movies now, there could have been another had Drew not turned down the role. Before Kate Beckinsale took on the role of Adam Sandler’s character’s wife in Click, Drew was offered the part. The reason behind this hasn’t been publicized, but it could be because of conflicts with Fever Pitch, which she starred in and produced.

But now that it’s been a whole ten years, we’re due for another Drew and Adam collaboration. Drew said on The Drew Barrymore Show that she, Adam, and Jennifer Aniston talked about doing a Three’s Company Reboot. In March 2023, Drew told ET Online that they were “actively seeking” their next project, but they’re waiting until they know it’s the right one.

“I know, I wonder the same thing, ’cause I think that is important for us, to hook into it,” Drew added. “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. It’s like an alchemy, you know? And it’ll be a little of this, a little of that.” Regardless, we’re excited for whatever this and that are.