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The Best Woody Allen Films
We asked local film buffs to pick their favorites.
Four-time Oscar winner Woody Allen (Annie Hall, Hannah and Her Sisters, & Midnight in Paris) is arguably the most prolific filmmaker working today. He’s also one of the most beloved.

He has received more Oscar nominations for best original screenplay than any other person to date; his current tally stands at fifteen nods and three wins -- for Annie Hall (1977), Hannah and Her Sisters (1986) & Midnight in Paris (2011). He’s been nominated for best director a total of seven times to date, and won for Annie Hall.

He’s directed fifteen actors who received Oscar nominations in all four acting categories (lead actor/actress and supporting actor/actress) with five going on to win. In the case of one-time frequent collaborator Dianne Wiest, she won the supporting actress prize twice for performances given in Allen films, her first was for Hannah and Her Sisters, and her second was for Bullets Over Broadway (1994).

This Friday, Blue Jasmine, his 43rd feature film, will open here in Milwaukee. The film stars Oscar winner Cate Blanchett as the title character – a disgraced New York City socialite (think Ruth Madoff by way of Tennessee Williams’ Blanche DuBois) who flees the city and resides with her blue collar sister (Sally Hawkins) in San Francisco after her businessman husband’s (Alec Baldwin) corrupt wheeling and dealing gets him sent to prison, and she’s left virtually penniless by the government.

After I attended a critics screening of the film, I was asked by a friend -- who has never seen a Woody Allen film from start to finish -- which of Allen’s films was my absolute favorite, in 200 words or less.

My answer: Without question, The Purple Rose of Cairo (1985). The reason I love that film as much as I do is because it’s Woody’s love letter to film, a medium I love as well. The movie makes me laugh, breaks my heart, and inspires me every time I see it. The performances are superb, particularly from leads Mia Farrow and Jeff Daniels -- those two are an absolute joy to watch together. Who, besides Woody Allen, would have ever attempted to create a romantic fantasy centered around a lonely and abused woman in the Great Depression who finds some solace from her bleak existence by frequenting the movies? The Purple Rose of Cairo deftly balances comedy and pathos which is very tricky to pull off. I like to think of the film as his underappreciated gem, which it is.

In light of Blue Jasmine's local theatrical release, Moviegoers asked people with ties to the local film scene to discuss their favorite Woody Allen films.

Ashley Altadonna, Tall Lady Pictures founder & local filmmaker:

Take the Money and Run (1969) is fabulous mockumentary. The scene where the two rival gangs of bank robbers show up to rob the bank at the same time always kills me!”

Tom Fuchs, Moviegoers staff blogger:

"There's so many to choose from, but I'll have to go with Crimes and Misdemeanors (1989). I think it's a perfect encapsulation of his best comedic and dramatic work and a tidy encapsulation of his worldview all wrapped into one brilliant bit of filmmaking. Match Point (2005) remade the dramatic portion of the film to pretty decent ends, but when you combine that story with a comedic counterpoint like he does [with Crimes and Misdemeanors], it's amazing.”

Susan Kerns, teacher & local filmmaker, former Milwaukee Film Education Director:

"I was introduced to Woody Allen as a kid when films like Bananas (1971) and Sleeper (1973) played seemingly constantly on HBO. I’m sure I saw Everything You Always Wanted to Know About Sex * But Were Afraid to Ask (1972) that way too -- and understood only that my parents wouldn’t want me watching it. I didn’t realize that Allen was an iconic filmmaker then; I just thought Mel Brooks and he made all the comedies, and I liked it that way. In college, people started telling me I looked like Mariel Hemingway in Manhattan (1979). I did. Sadly, I don’t anymore. After watching it, I fell in love with “the other Woody Allen,” the one who made Manhattan, Hannah and Her Sisters, and Annie Hall. The latter continues to be my favorite and the film of his I return to most. Diane Keaton is amazing, and I think Annie Hall resonates with anyone who has grown up in the Midwest and spent time in New York (or vice-versa). Allen absolutely nails that dynamic. Plus, “We can walk to the curb from here” is the best way to justify a poor parking job. It’s definitely the movie line I quote most."

Graham Killeen, local film/theater director, teacher & film critic:

“There's a deep reservoir of melancholy that runs through even Woody Allen's goofiest comedies that always reminds me he's not just making us laugh, he's making cinema. Nowhere are his humor and despair more deftly intertwined than in Love and Death (1975), and the last shot where Allen blithely dances away with the grim reaper is an absolutely perfect metaphor for him as a filmmaker.”

Jon Kline, organizer, Milwaukee Artist Resource Network (MARN) movies:

Everything You Always Wanted to Know About Sex* But Were Afraid to Ask. Not many directors can go so far into silliness and still keep an audience. It probably taught me a few things, too.

Kyle Laurent, film critic & teacher:

“For me it's Annie Hall. I know it's not a "deep cut" into Allen's library but it's my favorite. It was the first movie I saw where I thought, ‘Oh, you can do THAT in a movie?’ I love how it blended styles and formats. It was the first movie I saw where a character broke the fourth wall and talked directly to the audience. It's also the first romantic movie I saw where they don't live happily ever after.”

Rebecca Merle, actress & filmmaker:

“I love Woody Allen films no matter the period in which they were made. It’s hard to believe he is only hitting his box office highs now. He brings an authenticity to drama and humor that resonates with almost anyone. Play It Again, Sam is that one film I cannot shake loose and I often turn to when I need a laugh – the antics of Woody as the loveless Allen (his real first name) still evokes hysterical laughter. Close runners up for bits that really make me smile are the cello teacher in Take the Money and Run, the cookie causing salivation in Small Time Crooks, and Harry’s soft focus in Deconstructing Harry -- there are simply too many good bits to name them all. I hope to work with him one day myself.”

Chris Sonnleitner, local filmmaker:

Everything You Always Wanted to Know About Sex* But Were Afraid to Ask.

The sheep segment with Gene Wilder will silence any crowd. It's the kind of silence where your body cannot even begin to laugh because the entire sketch is just too much. Comedy gold, sir. Comedy gold.”

Jared Stepp, co-founder, Ideogram Films & producer of the 2013 48-Hour Film Project Milwaukee:

“As a producer/director, I appreciate Bullets Over Broadway. The comedy is catered to performance artists.”

What's your favorite Woody Allen film? Sound off in the comments section below.

Images courtesy of Shutterstock. 

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