“Zelig” (1983) Woody Allen’s finest achievement: a fantasy about a perennial eyewitness that’s even better than its New Yorkerish literary conceit, thanks in no small measure to the genius of cinematographer Gordon Willis. Unlike anything else ever made in America (please don’t tell me about “Forrest Gump”). In its own way, a very personal film, too.
“Manhattan” (1979) The devilishly funny, personal and, courtesy of Mariel Hemingway, lovely and touching film about the way that Allen’s complex personal life would soon come to obliterate his public esteem.
“Crimes and Misdemeanors” (1989) Not nearly as weighty as it thinks it is, but much more so than most Allen films. Martin Landau is the standout.
“Annie Hall” (1977) One of the two always-mentioned Allen classics (see the following) – too much so to be truly great, but the ultimate tribute to the way Diane Keaton once functioned as his muse.
“Hannah and Her Sisters” (1986) Overrated perhaps, but a terrific film whose performances by Michael Caine and Barbara Hershey demonstrate how powerful Allen’s non-method approach can be with great actors.
“Mighty Aphrodite” (1995) Allen actually allows himself to get a little dirty. Mira Sorvino, who won an Oscar, helps the cause.
“Deconstructing Harry” (1997) Perhaps the most underrated Woody Allen movie of the past 20 years – a truly wickedly funny portrait of a writer resembling Philip Roth (a friend of his estranged partner Mia Farrow).
“Broadway Danny Rose” (1984) He seems to have meant it to be heartfelt. Sometimes it is, especially if you know anything about how much Allen might owe to his longtime agent Jack Rollins.
“Match Point” (2005) Without doubt the biggest surprise on the entire Allen filmography – a plausibly Hitchcockian suspense thriller made in late life.
“Wild Man Blues” by Barbara Kopple (1997) Kopple’s documentary about Allen the clarinetist on tour accidentally became the greatest film about the appalling tabloid version of his life. It’s the most important film for anyone to see to understand his once-controversial relationship to Soon-Yi, who functions brilliantly the way so many musicians’ wives do – as the ultra-competent manager of Woody Allen Inc. They are still together 16 years later.
– Jeff Simon