27. The Holiday (2006)
Two romances for the price of one: English Kate Winslet, trying to get over a broken heart, swaps houses at Christmastime with Californian Cameron Diaz, who's trying to figure out why she doesn't seem to have a heart. One of the best scenes in this movie is when Winslet arrives in LA, sees Diaz's home, and jumps up and down around the house -- the way we'd act if life suddenly dropped us in a Nancy Meyer movie home. Winslet, as always, is great in this movie, but this is Diaz at her height: awkward, anxious, adorable, and someone with whom you want to drink a bottle of wine (ideally with both of you wearing one of the perfect-for-wine-drinking cardigans she wears in this movie). Diaz has the better of the two romances -- no offense, Jack Black, but you're no Jude Law -- but the subplot with Winslet and the elderly neighbor tugs at your heartstrings.
Where to watch it: Rent on iTunes, Amazon, Vudu, and YouTube