Allen began his career as a performer with a nightclub act in which he was the butt of his own jokes. He was popular on college campuses and a frequent guest on television shows. Allen began his screenwriting career with What's New, Pussycat? (1965), which he directed and in which he also played a part. He went on to become one of the best-known American actor-directors for a series of mordant comedies in which he usually played a bumbling, anxiety-ridden but generally cultured Everyman. They include Take the Money and Run (1969), Bananas (1971), Sleeper (1973), and Love and Death (1975).
Starting in the late 1970s, Allen's films began to explore more serious themes -usually matters of the heart, in all their pain and perplexity. Most were bittersweet comedies, set in New York City and starring Allen opposite Diane Keaton or Mia Farrow. Annie Hall (1977) won the Academy Award for best picture, and Allen for best director; he also shared the best original screenplay award. He won another Oscar for best screenplay for Hannah and Her Sisters (1986).
Allen's other films (he usually released one per year) include Everything You Always Wanted to Know about Sex … (1972); Interiors (1978), a somber drama that paid homage to Ingmar Bergman, whom Allen long admired; Manhattan (1979); Stardust Memories (1980); A Midsummer Night's Sex Comedy (1982); Zelig (1983), a faux-documentary about a human cipher whose infinitely variable personality puts him into many of the 20th century's greatest events; Broadway Danny Rose (1984); The Purple Rose of Cairo (1985); Radio Days (1987); Another Woman (1988); Crimes and Misdemeanors (1989); Alice (1990); Husbands and Wives (1992); Manhattan Murder Mystery (1993); Mighty Aphrodite (1995); Everyone Says I Love You (1996), which incorporated 1930s-style musical numbers into its 1990s story of the lives and loves of affluent Manhattanites; Sweet and Lowdown (1999), with Sean Penn as a talented but clueless, fictional 1930s jazz guitarist; Small Time Crooks (2000), which charmingly harked back to some of Allen's earlier small comedies; Melinda and Melinda (2004); Match Point (2005); and Scoop (2006). Vicky Cristina Barcelona (2008) garnered him the best critical response in years -and won actress Penélope Cruz an Academy Award for her role as the fiery Maria Elena.
Allen's next film, Whatever Works (2009), did not fare as well—nor did You Will Meet a Tall Dark Stranger (2010). Allen's film Midnight in Paris, a nostalgic trip to the Paris of Hemingway and Gertrude Stein, premiered at the Cannes Film Festival in 2011; it provided Allen with good reviews and some box-office heft (it won an Academy Award for best original screenplay, as well). He followed that film with To Rome with Love (2012). Allen wrote and directed Blue Jasmine (2013), which featured an Academy Award–winning performance by Cate Blanchett as a Manhattan socialite headed toward a breakdown. His next film, Magic in the Moonlight (2014), is about a magician (Colin Firth) who seeks to expose an attractive fortune hunter passing as a spiritualist; it did not fare as well with the critics. (Allen also acted in The Front, 1976, a dramatic film about blacklisting in Hollywood, and Scenes from a Mall, 1991, a coolly received Paul Mazursky comedy in which he starred opposite Bette Midler.)
Allen's first play, Don't Drink the Water, opened on Broadway in 1966, and he made his stage acting debut in Play It Again, Sam (1969). Allen is the author of Getting Even (1971), Without Feathers (1975), Side Effects (1980), and numerous magazine pieces. For decades he played his clarinet on Monday nights at Michael's Pub in New York City, and in 1996 Woody Allen and His New Orleans Jazz Band made a successful 14-city European tour that was captured on film by the documentarian Barbara Kopple in Wild Man Blues (1997). Allen's long personal and professional association with Mia Farrow ended in 1992 amid a bitter custody fight, which he lost, over their three children; he subsequently married one of Farrow's adopted daughters, Soon-Yi Previn.