The Pen in Hand Guide to the Movies: The Legacy of Woody Allen

Illustration by Michael DiMilo

By Geoff Carter

Woody Allen; Attribution:
Colin Swan, CC BY-SA 2.0, via Wikimedia Commons

He is a legendary filmmaker whose career has spanned fifty-some years—and has worked with everyone from Diane Keaton to Cate Blanchett to Scarlett Johannson to John Cusack to Michael Caine—and more. He has worked in nearly every film genre imaginable—slapstick, romantic comedy, historical features, mystery, documentary, psychological drama–everything except maybe science fiction or fantasy; no wait, I forgot Midnight in Paris and Sleeper.

Starting out as a stand-up comic and comedy writer, Allen worked his shtick into rambunctious comedies like Take the Money and Run, Play it Again, Sam and Bananas, but as he grew into his role as writer and director, his films took on complexities and sophistication almost unparalleled in modern cinema. The poignancy of Hannah and Her Sisters and Broadway Danny Rose and the psychological twists in Blue Jasmine are almost unsurpassed. The tension of Match Pointand Crimes and Misdemeanors are as good as anything in neo noir. And his movies nearly always simultaneously function as a vehicle for Allen’s wit (often performed by himself).

He is one of the most unique voices in American cinema, and at eighty-nine, he is actively working on his latest endeavor, Coup de Chance.

Trying to pick Woody Allen’s ten best films is a little like picking the ten coolest cars or the ten tastiest hamburgers in the world. Choosing the top ten of anything is at best subjective, at worst random. Beauty, after all, is in the eye of the beholder.

Of course, Woody Allen’s career cannot be considered with mentioning his personal—alleged—transgressions. While embroiled in the scandals surrounding his and Mia Farrow’s adopted children, Allen’s reputation and image became tarnished, but those horrible allegations surrounding his personal life have not seem to have diminished his reputation as one of the world’s premier screenwriters and film directors.

The Ten Best Woody Allen Movies

(In no particular order…)

Manhattan (1979): A romantic comedy about the tumultuous life of Alvy Singer, a divorced comedy writer who is dating a seventeen-year-old named Tracy (Mariel Hemingway) but throws her over for the beautiful but neurotic ex-mistress Mary (Diane Keaton) of his best friend Yale (Tony Roberts). Shot by Gordon Willis in beautiful black and white, the film is a loving tribute to New York City, which Allen maintained was almost a character in the film. The poignant ending is a tribute to vagaries of love and the value of innocence. Notable for a brief but memorable appearance by the great Meryl Streep.

Annie Hall (1977): Arguable Allen’s breakout film, Annie Hall was not only an engaging romantic comedy, it stretched the envelope of film convention by subtitling character thoughts under dialogue—to hilarious effect, used double exposure to reveal characters’ inner and outer selves, and even allowed Allen to pull Marshall McLuhan out a line for the theater to prove a point. While Diane Keaton had previously received accolades for her performances in Looking for Mr. Goodbar and The Godfather I and II, Annie provided the vehicle for what would become her comic persona. Notable for a brief but memorable—and frightening—appearance by Christopher Walken.

Love and Death (1975): Allen’s comedic take on the historical epic—specifically Tolstoy’s War and Peace. As pacifist and intellectual Boris Grushenko, Allen tries to avoid service during the Napoleanic Wars but is drafted into the Russian Army. In love with his cousin Sonja (Diane Keaton), he is devastated to learn she has married a herring merchant, and in his disappointment and anger, he somewhat becomes a war hero. He returns and marries his widowed cousin—with whom he has a number of hilariously elliptical philosophical discussions. When he is forced to return to service, Sonja concocts an ill-fated plan to assassinate Napolean. Notable for a short appearance by Jessica Harper.

Broadway Danny Rose (1984): A poignant portrait of Danny Rose (Woody Allen), a loser of a talent agent who represents bad acts including ventriloquists, animal acts, and worse. Lou Canova (Nick Apollo Forte) is an over-the-hill lounge singer represented by Danny who because through an unexpected wave of nostalgia, is suddenly popular again. Lou wants his girlfriend Tina (Mia Farrow) to accompany him to a big gig at the Astoria and asks Danny to bring her. Dodging mishaps and danger (including her gangster ex-boyfriend) Danny delivers her to the gig where Lou is a big success and decides—like many of Danny’s clients—to leave for better representation. Tina, regretting persuading Lou to drop Danny, comes back to him. The narrative is notable for being framed as a story told by a group of comedians in New York’s Carnegie Deli.

Hannah and Her Sisters (1986): Another New York City story about three sisters—Hannah (Mia Farrow) the self-sufficient foundation of the family, Lee (Barbara Hershey) who is living with a much older artist (Max Von Sydow) and Holly (Dianne Wiest) who is searching for a direction in life. The film begins and ends on Thanksgiving Day at Hannah and her husband Elliot (Michael Caine)’s beautiful home. Elliott discovers he has a crush on Lee and persuades her to have an affair with him. Holly—hating herself—relies heavily on Hannah’s moral and financial assistance. The siblings’ stories cross borders of infidelity, pride, accomplishment, love, and finally redemption. A beautifully written movie that is impeccably acted by the entire company. Notable for Dianne Wiest’s breakout performance. Also featuring performances by Carrie Fisher, Sam Waterston, Lloyd Nolan, and John Tuturro.

Zelig (1983): Probably one of Allen’s oddest groundbreaking achievements, this mockumentary follows the life and exploits of Leonard Zelig (Allen), a human chameleon who takes on the qualities and mannerisms of the people around him. He first catches the attention of F. Scott Fitzgerald for one moment hobnobbing with the rich and in the next taking on the opinions and mannerisms of the kitchen help. Psychiatrist Dr. Eudora Nesbitt Fletcher (Mia Farrow) tries to help Zelig and discovers that his ability comes from a desperate need to be accepted. After a series of mishaps, the two fall in love, and ultimately live happily ever after. Notable for Allen’s use of documentary film techniques to tell the story of a man who will do anything to be accepted.

Crimes and Misdemeanors (1989): A dark and convoluted tale of a wealthy ophthalmologist Judah (Martin Landau) torn between his lover Dolores (Angelica Huston) and his family. Feeling cornered, he contacts his brother-in-law Jack (Jerry Orbach) to have Dolores killed. Meanhwhile, filmmaker Cliff (Allen) is forced by financial hardship to make a documentary about his pompous brother-in-law Lester (Alan Alda) to film his life story. After falling in love with—and being rejected by Lester’s associate producer Halley (Mia Farrow), he becomes despondent. The film ends with Judah having completely forgiven himself and Lester winning the heart of Halley. Cliff is left alone, wondering about the meaning of life. Notable for Sam Waterston’s portrayal of Ben, a blind rabbi.

Bullets Over Broadway (1994): A black comedy set in 1940s New York. Aspiring playwright David Shayne (John Cusack) tries to get financing for his play by hiring Olive Neil (Meg Tilly), the girlfriend of a notorious gangster. Disappointed with Olive’s personality and lack of talent, Shayne turns to Helen Sinclair (Dianne Wiest) a fading and alcoholic actress as his lead. Things get hot when Cheech (Chaz Palimenteri) turns up at rehearsals to make sure Olive is getting enough exposure. Seeing that Cheech has a great talent for writing, the cast redoes the script, producing a hit, but things get hot when Olive’s boyfriend accuses Cheech of getting rid of her. Notable for appearances by future Sopranos stars Edie Falco and Tony Sirico.

Sweet and Lowdown (1999): A mockumentary about self-centered jazz guitarist Emmet Ray (Sean Penn) and his affair with a mute laundress Hattie (Samantha Morton). Framed as a documentary, the narrative is broken into by commentary from real-life historians, authors, and jazz critics. After recording some tracks for RCA Victor, Ray disappears from public view. He meets Hattie and, despite communication difficulties, the two of them form a close bond, but Ray eventually throws her over, believing a musician of his stature should have a higher social standing. He marries Blanche Williams (Uma Thurman) who eventually rejects him. Ray goes back to Hattie only to discover she is happily married. Notable for Morton’s superlative performance as Hattie.

Blue Jasmine (2013): In this Woody Allen production, Blanchett plays “Jasmine” Francis, a socialite who has fallen on hard times. Her money-manager husband Hal (Alec Baldwin) has been arrested for defrauding her clients and subsequently commits suicide in prison. Broke, and with nowhere else to go, Jasmine travels to San Francisco to stay with her sister Ginger (Sally Hawkins) and her boyfriend Chili (Bobby Cannavale), whom she loathes because she considers him “beneath” her. Jasmine meets Dwight (Peter Sarsgaard) a wealthy ambassador whom she tries to seduce, but when he discovers she has lied to him, he dumps her. Jasmine has an argument with Ginger and Chili and moves out. Blanchett’s performance as the brittle, wheedling, and demanding Jasmine is outstanding. She shifts roles from Jasmine as manipulator to victim to snob as effortlessly as a Ferrari going from zero to sixty. Notable for an early appearance by a brief appearance by Michael Stuhlbarg.