Sideways (2004) **** [Payne Train Pt. 4]

As a teetotaler, all of the "wine stuff" in Sideways (2004) went over my head—though the situations and dialogue are very amusing—but I still loved the film. With his fourth feature, Alexander Payne strikes a near-perfect balance of breezy comedy and thought-provoking existentialism, succeeding in making the audience care about two deeply flawed human beings. To quote my friend Sean (whose insistence spurred this "Payne Train" filmography deep dive), Sideways is an "authentic meditation (of) masculinity, 

 vulnerability, and ego." An incredibly honest and funny film about life, loneliness, and the search for meaning—you know, relatable midlife crisis stuff.

Alexander Payne Feature Films Ranked