Not a member? Sign up now
24. Bullets Over Broadway (1994)
Few filmmakers are as preoccupied with genius and its trappings as Woody Allen. This funny, though flawed, film focuses on the behaviors that artists believe they're entitled to once they've been validated as geniuses. Chazz Palminteri's performance, as a gangster who turns out to be a brilliant playwright, is inspired.
23. Sweet And Lowdown (1999)
Allen strayed from his comfort zone to direct this dramatic picture about a troubled jazz musician, a somewhat bright spot in his '90s work. Allen's personal passion for jazz comes across in the film's period-perfect music, but Sweet And Lowdown's leads, Sean Penn and Samantha Morton, really carry it.
22. Radio Days (1987)
Similar in tone to the stronger Purple Rose of Cairo, Radio Days was another mid-'80s Allen picture that dealt romantically — critics might say sentimentally — with the escapes provided by entertainment. Its semi-autobiographical nature is obvious in the way that Allen so lovingly and confidently captures the milieu — a big Jewish family living in Rockaway Beach in the '30s.
21. Anything Else (2003)
This was one of Allen's most hated films of the past decade, but unjustly so. While it certainly pillages from the Allen canon (especially Annie Hall), it's not bad when viewed out of that context. Jason Biggs's performance doesn't exactly hide why his career's turned out the way it has, but Christina Ricci is bewitching, and Allen sparkles as the wack-job pseudo-mentor to Biggs. The scene where Allen takes a tire iron to a car windshield is one of the best he's ever performed in.
20. Bananas (1971)
This film is often grouped alongside Love and Death and Sleeper as the best of Woody's "early, funny ones," and while it's the earliest (and weakest) of the three, it still offers up its fair share of laughs, including an absurdist turn by Howard Cosell that, sadly, has severely dated the film. The scene where Woody's guerilla leader orders lunch for his army — "500 grilled cheeses, one with tomato" — is priceless.
19. Vicky Cristina Barcelona(2008)
A Woody picture making money! Again! After Match Point's success a few years earlier, this picture's reception made it clear that Allen's European sojourn had resuscitated his career to a degree. Light on the one-liners and heavy on the theatrics, the film could only have worked with hot-blooded performers like Javier Bardem and Penelope Cruz — but it did. It also features a breakout performance from Rebecca Hall.
18. Everyone Says I Love You (1996)
Perhaps the last time Woody really pushed himself in terms of genre exploration, this film is a comedy-musical hybrid not unlike the ensemble pictures he loved as a youth. It works better than you might expect, with a surprisingly touching performance of "I'm Through With Love" from the director himself. A few roles do seem miscast — never has Edward Norton been more toothless — but the neurotic Upper West Side Jewish clan is written with zest.
17. Hollywood Ending (2002)
One of Allen's most underrated films, Hollywood Ending was reviled when it was released, but the concept is intrinsically funny — a director trying to make a Hollywood film while blind — and Allen runs with it nicely. Treat Williams is excellent as the sleazebag Hollywood producer.