5. 50 First Dates (2004)
Along the same bent as Big Daddy,
50 First Dates is one of Sandler's sweeter outings, this time dealing with romance rather than a father-son bond. Sandler plays Henry Roth, a womanising vet at a sea-life park whose life is inexorably changed when he meets Lucy (Drew Barrymore), who suffers from a special type of amnesia that makes her forget everything of the previous day when she wakes up. It's an absolutely barmy premise, but a unique one around which to wrap a romance, an inspired
Groundhog Day-esque yarn that sees Henry trying to get Lucy to fall in love with him again every single day. If a premise like this is executed poorly, it would end up creepy and anything but funny, but Sandler thankfully guides it home, in large part due to the excellent chemistry with Barrymore, who previously sparked with him on The Wedding Singer. It's a Sandler film with real heart and intention, but is also suffused with some hilarious cameos, specifically Sean Astin, completely throwing himself into the role of Lucy's steroid-addicted brother. Sure, the ending is absolutely absurd, but it's sweet-natured, and sometimes that's enough. It currently sits at 44% on Rotten Tomatoes despite being one of Sandler's minor commercial successes.