Lasciate ogne speranza, voi chi’intrate. How did it come to this? At the height of his power in Hollywood in 1999, Adam Sandler founded his own production company as a way to continue making the movies he enjoys. Over the years his films have slowly morphed into a pariah on the landscape of big budget studio comedies, becoming thinly veiled excuses for lavish vacations. But do they truly represent the nadir in the career of one of comedy’s once-brightest stars? Are there any hidden or underrated gems? Is there such a thing as too few fart jokes? Will I retain any sense of sanity by the end of this? Join me and find out, as we venture to the Happy Valley.

In a strange way, 50 First Dates has always felt to me like one of those culturally ubiquitous movies — not unlike It’s A Wonderful Life or Snow White and the Seven Dwarfs, where a viewer can essentially know the crux of a film and all of its story and character beats simply by reading the plot description. Of course, treating a film in this way ultimately cheapens the experience of actually seeing a film for itself and truly understanding its intentions. Shortly after its release, I can remember hearing the main plot of 50 First Dates explained to me: A man (Adam Sandler) falls in love with a woman (Drew Barrymore) who suffers from short-term memory loss and stumbles upon an elaborately constructed ruse that her family and friends have put together for her to shield her from emotional pain — and writing the film off as an insanely over-complicated backdrop for a romantic comedy. In some ways, I wasn’t wrong. Sit and think for too long on the plot of 50 First Dates and your brain will probably explode.

And yet the film isn’t entirely sunk by its insane premise. For that, we can thank the incalculable chemistry between Sandler and Barrymore, returning to star together after 1998’s The Wedding Singer. Chemistry is a powerful weapon in a filmmaker’s arsenal. It’s part of what made the Katharine Hepburn-Cary Grant films so great; same with Ben Affleck and Matt Damon or Seth Rogen and James Franco. Sure, stars can be forced together by their directors to create chemistry, as evidenced by the cast of Platoon or insert any other war-drama-directed-by-a-crazy-person here. But when a duo can channel each other over multiple films, anything can happen.

In the case of 50 First Dates, it also helps that Sandler is re-teaming with Peter Segal, director of his then-most recent film (Anger Management). Perhaps better than any director that Sandler had worked with at the time, aside from Paul Thomas Anderson, Segal knew how best to rein in Sandler’s goofy tendencies to create a more human-adjacent character. Management, you may recall, had its issues, but Sandler wasn’t the primary one. This film undoubtedly still feels like a Sandler vehicle — see the SPAM product placement, Rob Schneider, the entire scene in the mental hospital, etc. — but Segal is able to utilize the best of Sandler by essentially making him the straight man in this bizarro world upon which he stumbles.

One element to 50 First Dates aided by the gift of hindsight is how this film has become emblematic for the larger part of Sandler’s later career. It’s easy to see how the film can be treated as the Patient Zero of Sandler’s post-2000s filmography, where he simply makes films with his friends as an excuse to go on fantastical vacations. Filmed on location in Hawaii, the primary cast is padded out with plenty of Sandler’s frequent conspirators: Schneider, Allen Covert, Peter Dante and a barely noticeable appearance by Kevin James. 

Would this movie be received completely differently if it was produced about 10 years later, after audiences had largely turned on Sandler? Perhaps, but the saving grace of the film is its humanistic storytelling. Calling 50 First Dates nuanced may be a stretch, but Barrymore’s Lucy feels like a real-enough person, and her trauma is treated with enough respect that the film doesn’t break under the weight of its own premise. There are certainly lesser films with characters like Lucy that either don’t dedicate enough time to her or try to make her affliction something easily solvable. Barrymore is one of the most underrated actresses of her generation, and to the extent that 50 First Dates succeeds, it’s because of her.

  • “I’m Getting Paid How Much?!” Inexplicable Cameo Award: Noteworthy for being one of the last live-action Dan Aykroyd film appearances for many years.
  • Just Go With It: The Happy Madison Promise. The opening gimmick of Sandler’s character as a womanizer feels completely unnecessary given how quickly it’s forgotten and never pays off.
  • Fart Joke Counter: None, but what’s with all the jokes about walrus penises?
  • The Walkout Test: Pass.

NEXT TIME: Sandler jumps back on the remake machine with an “update” to the 1974 Burt Reynolds vehicle The Longest Yard.