25. Groundhog Day (1993)
Image Source: Nerdist
Bill Murray in a romantic comedy? Yes, please. Regardless of what day it is, Groundhog Day is an ideal romantic comedy to watch. The film transcended an easily forgettable holiday and found something incredibly romantic in being caught in-between seasons. Murray plays Phil Connors, a self-loathing TV reporter trapped in a time loop to last more than 40 years. This gives him enough time to successfully court Rita (Andie MacDowell). It is charming, and all-around worth repeating again…and again…and again.