Louise Lasser, Bananas
The second Mrs. Woody Allen was in six of his films, counting voice work in his feature directorial debut, 1966's What's Up, Tiger Lily? Allen, 24, was married when he met Lasser, 21. "We immediately, immediately, just were meant to be in the same playpen," she recalled in a 2013 interview. They divorced in 1970 after four years. Asked if the breakup scene in Bananas was based on their break-up-to-make-up tendencies, she said, "We finally ended up improvising it, but it could have been that I was the girl then that things were based on."
Diane Keaton, Annie Hall
The most famous of her eight collaborations with Allen is Keaton's Oscar-winning turn as the spirited, analytical girlfriend who's driving him mad in the 1977 classic, also a winner for Best Picture, Best Director and Best Original Screenplay.
Mariel Hemingway, Manhattan
The 1979 comedy is considered a classic, but 17-year-old Mariel playing a 17-year-old who dates Allen's twice-divorced, 42-year-old screenwriter has always been weird. Hasn't it?
Mia Farrow, The Purple Rose of Cairo
Allen's off-screen partner starred in 13 of his films between 1982 and 1992 before their messy breakup.
Charlotte Rampling, Stardust Memories
The French goddess helps Allen go meta in this romance about a filmmaker recalling the past loves who inspired him.
Mia Farrow, Barbara Hershey and Dianne Wiest, Hannah and Her Sisters
That's the ever-stable Hannah and her flaky, resentful-then-remorseful sisters, left to right. Allen won a Best Original Screenplay Oscar and Wiest won the first of her two Best Supporting Actress Oscars. (Michael Caine also won Best Supporting Actor, the only one of five male acting nominees from an Allen film—including Allen himself—who's actually won.)
Anjelica Huston, Manhattan Murder Mystery
The Oscar winner helps Allen and Diane Keaton's nosy New York couple solve a Rear Window-reminiscent crime in this 1993 comedy but got the short end of Allen's hope for mankind as Martin Landau's impatient mistress in Crimes and Misdemeanors.
Mira Sorvino, Mighty Aphrodite
Sorvino was a lock for the Best Supporting Actress Oscar for her role as a hooker with a heart of gold (and a hilariously high voice) in the 1995 comedy.
Penélope Cruz, Vicky Cristina Barcelona
The Spanish beauty scooped up a Best Supporting Actress Oscar for her role as Javier Bardem's seductive and unstable ex-wife in the 2008 romance.
Judy Davis, Husbands and Wives
The Australian star of stage and screen has been in six Woody Allen films, including his upcoming as-yet untitled romantic comedy due out in 2016.
Dianne Wiest, Bullets Over Broadway
Another Best Supporting Actress win for Wiest as a stage diva who's got the playwright (and the rewrite guy) silently wrapped around her little finger.
Drew Barrymore, Everyone Says I Love You
She's a happily engaged woman with a sprawling family who starts to question her choices in this boisterous 1996 musical comedy.
Samantha Morton, Sweet and Lowdown
The British actress plays a mute woman who's charmed—and then repulsed—by Sean Penn's talented but self-sabotaging jazz man.
Charlize Theron, Celebrity
Allen skewers the biz in this comedy about the vapid goings-on in Hollywood.
Helen Hunt, The Curse of the Jade Scorpion
She's the classy efficiency expert who unwittingly falls for Allen's insurance investigator in this period-caper comedy from 2001.
Radha Mitchell, Melinda and Melinda
The Australian actress stole the show playing two versions of the same character in Allen's 2005 what-if-this-comedy-was-a-tragedy hybrid.
Scarlett Johansson, Match Point
"It's very hard to be extra witty around a sexually overwhelming, beautiful young woman who is wittier than you are. Any time I say anything amusing, Scarlett tops me," Allen raved about ScarJo, whose first of three films for the director was this cynical drama about a social-climbing tennis pro who needs to silence his girlfriend before his rich fiancée finds out.
Evan Rachel Wood, Whatever Works
The savvy actress plays a naive runaway who winds up on Larry David's curmudgeonly New York doorstep and they inexplicably become an item (well, until she meets Henry Cavill) in the 2009 comedy.
Marion Cotillard, Midnight in Paris
Owen Wilson's starry-eyed screenwriter finds love with the French beauty during his forays into the City of Light's raging literary scene (in the 1920s) in this fantastical 2011 confection, for which Allen won a Best Original Screenplay Oscar, his fourth Academy Award.
Emma Stone, Magic in the Moonlight
Colin Firth's skeptic accidentally falls in love when he tries to expose Stone's beautiful clairvoyant as a fraud in this gorgeously shot period romance.
Cate Blanchett, Blue Jasmine
The Australian star sucked up every award in her path on her way to the Best Actress Oscar for her mesmerizing role as an increasingly delusional woman who went from riches-to-rags after her husband turned out to be a Bernie Madoff type.