Published at 7:00 AM on January 27, 2009
Jeremy Medina

By Jeremy Medina

He Adored New York City: Woody Allen's 10 Finest Films

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"I don't want to achieve immortality through my work...
I want to achieve it through not dying."
— Woody Allen

Love him or hate him, Woody Allen is the most prolific filmmaker of our time. Vicky Cristina Barcelona—released on DVD today amidst Oscar buzz for its star Penélope Cruz and a Golden Globe win for best musical/comedy—is his 39th feature film, an astronomical figure. Inevitably, not all of those 39 are completely original or entirely worthwhile, but that oft-recurring phrase “Woody Allen’s comeback film” should be retired for good. That phrase was placed on 1999’s Sweet and Lowdown, 2005’s Match Point and, for some, Vicky Cristina Barcelona. "Comeback" suggests he’s somehow left us. He hasn’t.

To be fair, Allen has produced some of his worst films this decade—with Anything Else, Hollywood Ending and Scoop standing as the biggest letdowns. But, as Barcelona wonderfully affirmed, when Allen is at the top of his game he’s still among the most talented filmmakers in the business. Now 73, Allen's got another film on deck for 2009—the comedy Whatever Works with Larry David. But instead of looking ahead, I want to take a step back and look at Allen's long, illustrious career that has given moviegoers so much laughter and joy; and so much to ponder, debate and analyze. Here is my estimation of his 10 best, keeping in mind that when it comes to the top three, it’s just personal preference.

10. Sweet and Lowdown (1999)

sweet_and_lowdown.jpgAllen's melancholic comedy on the emotionally vacant, self-destructive fictional jazz guitarist features two of the best performances in any Allen film to date, by two of the best actors in movies today: Sean Penn and Samantha Morton. Penn plays Emmet Ray, a talented but reckless musician who never commits to anything, least of all to a woman; Morton plays the mute woman who finally steals his heart. A whole world of human emotion is written across Morton's expressive face; she never speaks because she doesn't need to. It's a tremendous performance, matched only by Penn's. "I've made a mistake," Penn cries in the haunting final scenes, illuminating one of Allen's harshest recurrent themes: happiness is only recognized after it has passed. Once it's gone, it's gone forever.

9. Match Point (2005)

match_point.jpgMatch Point restored many's faith in Allen after a series of disappointments. Essentially a retread of half of Crimes and Misdemeanors—albeit a fine, glossy, expertly-paced retread—the film marked Allen’s key departure to Europe for the first of four efforts. Jonathan Rhys Meyers and Scarlett Johansson made for beautiful blanks for which he could project his lofty Dostoyevskian ideals, in a tale about murder and it's devastating mental and moral ramifications. Thematically dense yet consistently compelling, Match Point is the kind of thinking man’s thriller only Allen knows how to make.

8. Love and Death (1975)

love_and_death.jpgThe very best of Allen's "funnier, earlier films," Love and Death showcases Allen's two favorite themes (see title). The absurdist plot centers on a young couple (Allen and Diane Keaton) who plot to assassinate Napoleon in czarist Russia. Garbed in one ridiculous costume after another, Allen's character philosophizes on God, love, death and the meaning of life, in between zany antics and hilarious physical comedy. The balance between big ideas and featherweight comedy is seamless, making Love and Death the perfect segue into the more ambitious and complex films that followed.  

7. Vicky Cristina Barcelona (2008)

vicky_cristina_barcelona.pngWhat starts out as an innocent summer jaunt to Spain turns into a time of romance, discovery, and self-doubt for the film’s titular characters, finely played by Scarlett Johansson and Rebecca Hall. From its Spanish setting to its playful, sensual love scenes, Vicky Cristina Barcelona feels like a departure for Allen. But, in truth, the film is an evolution from Allen’s earlier works—another meditation on relationships, an exploration of people who find themselves confused by love and afraid of happiness. One thing is certain: there has never been and never will be another character like Maria Elena. Rapturously played by Penélope Cruz, she is the film’s indispensable beating heart.

6. Bullets Over Broadway (1994)

bullets_over_broadway.jpgWhile Dianne Wiest deservedly won an Oscar for her blissfully funny performance as an over-the-top actress (one who prides herself on "never playing frumps or virgins"), Bullets Over Broadway is one of Allen’s funniest films because of the excellence of its entire cast. John Cusack, Chazz Palminteri, Tracy Ullman and, miraculously, even Jennifer Tilly play off each other brilliantly. Allen’s endlessly quotable script (“don’t speak!”) contains key insights into art and morality, creating that rare, beautiful thing: a hilarious and thought-provoking comedy.

5. Crimes and Misdemeanors (1989)

crimes_and_misdemeanors.jpgAllen has long been fascinated by the idea of getting away with murder, the subject of one half of Crimes and Misdemeanors. The terrific Martin Landau plays a successful ophthalmologist who has the woman he had an affair with (Anjelica Huston) murdered because she threatened to destroy his carefully constructed lie of a life. The other half of the film tells the story of a struggling documentary filmmaker (Allen), trapped in a loveless marriage and in love with a woman (Mia Farrow) who does not reciprocate his feelings. Both stories are steeped in loss—a loss of happiness, faith and morality. When the two stories converge at the end, the results are nothing short of powerful.  

4. The Purple Rose of Cairo (1985)

purple_rose_of_cairo.jpgAllen has stated a number of times The Purple Rose of Cairo is among his favorite films he’s directed, and it’s no wonder—it’s his sweetest and most imaginative film to date. Mia Farrow delivered her best performance in the 13 films she made with Allen, playing a lonely woman who escapes to the movies to live out her fantasies through her favorite actors. Even when the dashing Tom Baxter (a young Jeff Daniels) steps out of the screen and into her life, she keeps her emotions and expectations in check: “I just met a wonderful new man. He’s fictional, but you can’t have everything.” Purple Rose whimsically builds toward a gut-wrenching, elegiac final shot that reminds us why we go to the movies in the first place: to dream.

3. Annie Hall (1977)

annie_hall.jpgAnnie Hall is, without question, Allen’s most recognized and influential film to date—and the sole best picture winner in his canon. The film is also one of the best romantic comedies ever, simply because it takes the time to show all of the moments that happen in a relationship—the wide spectrum of happy and sad, of bittersweet and just plain bitter. From fighting over which movie to see, to laughing while chasing down lobsters in the kitchen, Allen perfectly encapsulates the delicate beauty found in the highs and lows of a relationship. It doesn’t hurt that his wit and humor is perfectly matched by Diane Keaton, in her iconic, Oscar-winning performance. Funny with a perceptively intellectual undercurrent, Annie Hall is an enduring classic.

2. Hannah and Her Sisters (1986)

hannah_and_her_sisters.jpgThree delicately written and deeply felt stories are interlaced in Hannah and Her Sisters, a relationship dramedy that stands as one of Allen's best screenplays. Michael Caine plays a man married to Hannah (Mia Farrow) who is in love with his sister-in-law (Barbara Hershey). Dianne Wiest is the family screw-up and former addict who bounces from career to career and relationship to relationship aimlessly. Allen plays Hannah's ex-husband, a resident hypochondriac (what else?). Caine and Wiest deservedly won Oscars, but the entire cast is superb, pulling off the remarkable feat of creating characters that feel like they're part of a family—a wonderful, loving, screwed up, tangled family who depend on each other to survive, whether they like it or not.
 
1. Manhattan (1979)

manhattan.jpgThings that makes life worth living: Woody Allen's masterpiece Manhattan. Gorgeously shot in black-and-white and set against a backdrop of Gershwin's "Rhapsody in Blue," Allen’s ode to the city that never sleeps is a profound meditation on love and loss. Allen, Diane Keaton and Michael Murphy play jaded, self-absorbed adults who over-think and over-analyze every aspect of life. Mariel Hemingway beautifully plays Tracy, the young girl in love with Allen and the only character who is honest about her feelings, the only one with the capacity to love whole-heartedly. The other characters are too delicate, too bruised, and too cynical. When Tracy tells him “you have to have a little faith in people” in the film’s touching final scene, our hearts melt a little—love may be fragile and fleeting, but it’s worth the risk every time. Romantic, witty and bittersweet, Manhattan is impeccably crafted, and stands tallest among Allen’s multitude of towering achievements.

Honorable Mentions: The wistfully nostalgic Radio Days (1987); the brutally honest Husbands and Wives (1992); the tragically somber Interiors (1978); the futuristic farce Sleeper (1973); and the criminally underrated Small Time Crooks (2000).

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