1. Harold and Maude
A person committing suicide is never funny. A person who keeps trying to kill themselves in the most elaborate ways (hanging, burning, etc.) is dark comedy gold. “Harold and Maude” has always been a cult classic, and it was once called “the greatest love story of our time” in “There’s Something About Mary.” This may be the only time that won’t feel at all creeped out by two people 70 years apart falling in love. This is one of the few movies about romance that doesn’t feel shallow. “Harold and Maude” is that good, and you can never go wrong with a soundtrack filled with Cat Stevens.
2. When Harry Met Sally…
We can thank Rob Reiner for setting the bar high, and then setting the template for 20 years of horrible romantic comedies. “When Harry Met Sally…” does it right for so many reasons. Maybe that’s because it turned a rom-com hater into a believer, at least for its 96 minute running time. Maybe it’s because it never tries to create some implausible, cosmic true love to bring the characters together. Rather, it shows love as something that takes time. Mainly, “When Harry Met Sally…” hasn’t aged a day. Any references involving the 80s have only become funnier.
3. Punch-Drunk Love
Finally, a movie about love that isn’t about people who need to be together, but rather people who make each other happy. As deeply troubled and neurotic Barry Egan, Adam Sandler gives the best performance of his career. Despite shying away from all of the romantic cliches that typically define this holiday, this is a model story about love. Perhaps love isn’t about a card, a box of chocolates, and a lavish dinner. Maybe it’s just about playing the harmonium for your lover and telling them the truth, even if the truth involves you getting into trouble with a phone sex hotline.