1. Groundhog Day (1993)
When it comes to the best comedies of the ’90s, the top spot could really only belong to one film. Groundhog Day stars comedy legend Bill Murray as contemptuous TV weatherman Phil Connors sent to the small town of Punxatawney to cover their annual Groundhog Day event. However, Phil finds himself trapped in a time loop, and is forced to live the same day over and over until he learns to change his ways.
Andie MacDowell stars opposite Murray as Phil’s love interest, and Groundhog Day also features the talents of Chris Elliott, Stephen Tobolowsky, and Brian Doyle-Murray. However, the film’s success really hinges on Murray’s ability to embody the character of Connors – something that Bill Murray is able to do all too well. The slow transformation and seemingly endless suffering of Connors is something that Murray brings to life with apparent ease, selling the film’s time loop premise in a way that few actors could pull off.
There’s so much depth to Groundhog Day: it’s well-written, well-acted, and well-conceived. Everything about it feels intelligent and unconcerned: it’s a fun and vaguely fantastical romp that makes full use of Bill Murray’s ability to make almost anything seem funny. Basically, Groundhog Day is filled with smarts, heart, and enough laughs to make you want to relive it over and over and over. (And over.)
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