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10. Knocked Up (2007)
While Judd Apatow’s odd romance featured a testosterone heavy feel, it is a sweet-natured film that features fine performances from both Seth Rogen and Katherine Heigl. While the real stand-out happens to be Leslie Mann as Heigl’s uptight sister, all the actors are simply perfect throughout. Knocked Up also offers a terrific script and a gorgeous soundtrack courtesy of Loudon Wainwright III.
9. Garden State (2004)
Writer/director/actor (and probably caterer) Zach Braff also offered a great soundtrack, terrific actors and made one of the most irresistible romantic comedies in years. Both Natalie Portman and Peter Sarsgaard give scene-stealing performances as part of the trio of friends. Yet credit Braff for creating such a smart, enjoyable and listenable cinematic romance.
8. Harold and Maude (1971)
Hal Ashby’s inconceivably funny and painfully dark love story is a revelation. This May-December romance between Ruth Gordon and Bud Curt (a seventy-nine-year-old woman and a teenage boy) has become an unforgettable cult classic throughout the years.
7. L.A. Story (1991)
Steve Martin plays a “wacky weatherman” in this irreverent look at Los Angeles. This clever film, written by Martin and directed by Mick Jackson, merges fantasy and comedy in a delightful way. L.A. Story remains one of Martin’s best comedies that is energized by the dazzling chemistry he shared with Victoria Tennant (his then wife), and especially Sarah Jessica Parker.
6. Some Like it Hot (1959)
If you’ve ever questioned why Marilyn Monroe was a star, you merely need to rejoice in this magnificent film. Tony Curtis and Jack Lemmon on the run and dressed in drag are simply perfect in this classic directed by Billy Wilder. It works as a gangster movie, a romance and a comedy. Of course, the luminous Monroe proves it is sexy to be funny.