Take Six: The Best Romantic Comedies of the Last 25 Years.


Five wasn’t quite enough. In alphabetical order:

  • Enough Said (2013) – Plain-spoken and touching without forgetting to bring the funny. Plus, any list like this one needs to include an entry that doesn’t fade to black as the couple embrace in a trite-but-satisfying Hollywood kiss.
  • Groundhog Day (1993) – A list like this should also have one film that is only tangentially about the romance. In this case it came down to Harold Ramis’ film or Judd Apatow’s The 40-Year Old Virgin, and that’s just no contest.
  • The Proposal (2009) – Romcoms seemed almost dead when this relic washed up onto our shores, and yet Ryan Reynolds and Sandra Bullock showed us that charm (along with a winning formula and smart writing) can work miracles.
  • There’s Something About Mary (1997) – The Farrelly Brothers’ magnum opus is a clockwork comedy: Everything fits together perfectly, leaving us to marvel at the inspired elegance of “hair gel” and testicles caught in zippers.
  • The Wedding Singer (1998) – Yup, an Adam Sandler movie. But he and Drew Barrymore proved to be a potent onscreen couple, and the star’s love of his 1980s setting clicked in all the right ways. (The pair re-teamed for 50 First Dates, which is good but not Wedding Singer good. Their upcoming collaboration, Blended, looks awful.)
  • When Harry Met Sally… (1989) – Saving the best for last. Rob Reiner and Nora Ephron knocked this one out of the park, and spent the rest of their careers (I know, Reiner’s still working, but come on) trying to recapture this magic. It’s Woody Allen without the neurosis, and the best romcom of the last quarter century.