Bananas

When people talk about Woody Allen’s pure comedies, there’s a good chance that this is the Woody Allen movie they’re talking about. The story, about a guy (Woody Allen, of course) who becomes a South American dictator in order to impress a woman, is absolutely packed with gags from start to finish – at least two of them involving Howard Cosell. If you like anarchic, absurd gags, check out Bananas, undoubtedly one of the funniest Woody Allen movies.

Interiors

On the other end of the spectrum is Interiors, an entirely humor-free homage to Woody Allen’s idol Ingmar Bergman. Just because it ain’t funny doesn’t mean it ain’t good, though. Here’s a Woody Allen movie that does what all great drama does – punch you in the gut and then crawl inside your head and never leave. A lot of people don’t like Interiors because of its vastly different tone from most other Woody Allen movies (September and Another Woman excepted), but if you have an open mind there’s no reason for you not to dig it.

Annie Hall

This is probably the definitive Woody Allen movie, in that it’s a perfect blend between the early, funny, anything-for-a-laugh stuff and the more mature comedies and dramas Woody Allen would be known for later. It’s also a pitch-perfect depiction of a brief romantic relationship that has Woody Allen using every stylistic trick in his arsenal, including but not limited to: Subtitles, animation, breaking the fourth wall, celebrity cameos, long takes, and bad karaoke.

Hannah and Her Sisters

In our opinion, this is not only an essential Woody Allen movie, but probably the best movie Woody ever made. It has a massive ensemble cast too large to list here, and features several interconnected dramatic arcs involving the loves and losses of Hannah and her two sisters. It also features what is perhaps Woody Allen’s best performance on screen. Why wouldn’t you watch this movie?

Match Point

When Match Point came out in 2005, many people noticed that it was a change of pace for Woody Allen. Namely, it falls into the genre of “thriller,” which is not something very many Woody Allen movies came close to before then (maybe Crimes and Misdemeanors, which is excellent). However, Woody pulls this off with such confidence and deftness, it’s a wonder he hadn’t been making movies like this for ages. We don’t want to spoil the plot in case you haven’t seen it, but it’s a Woody Allen movie that will start out as a typical drama, but will end up holding you on the edge of your seat in a way that you probably wouldn’t expect from Woody Allen. Until now, anyway.

This is a mere handful of Woody Allen’s movies, who’s been churning out practically a movie a year for decades. But these five pretty much run the Woody Allen gamut, from light and ridiculous comedies to heavy and suspenseful dramatic thrillers. So if you’ve been living under a rock for those decades and haven’t checked any Woody Allen movies out, wouldn’t now be a good time?