41. The Wedding Singer (1998)
Adam Sandler has shown on more than one occasion over the last 25 years that there’s many more strings to his bow than the one-not comedy shtick, but he doesn’t show it anywhere near often enough.
The Wedding Singer was arguably the first time he demonstrated true potential as a romantic leading man, and he’s never generated better onscreen chemistry with anyone than the spark he shares with Drew Barrymore.
It’s very inconsistent in terms of tone, but the central romance greatly elevates the material, and the schmaltz and saccharine moments have cemented it as one of the most beloved movies of either star’s career.