Annie Hall (1977)

In what is probably still his best-known film, Allen is a full 10 years older than co-star Diane Keaton -- a significant but not necessarily scandalous margin. No wonder they don't end up together at the end.

Manhattan (1979)

Allen plays a 42-year-old divorce who celebrates his mid-life crisis by shacking up with a 17-year-old (played by Mariel Hemingway), only to cheat on her with a neurotic Keaton. Guess which one Woody ultimately chooses.

Midsummer Night's Sex Comedy (1982)
Hannah and Her Sisters (1986)
Crimes and Misdemeanors (1989)

The 1980s represented a tame decade for Allen as he began his 12-year relationship with Mia Farrow, who replaced Keaton as his creative muse. In between somber Ingmar Bergman knock-offs, he put forth some of his best-loved comedies, most of which dealt with marital infidelity of some form or another. All seemed well in Woody's world...until the '90s happened.

Husbands and Wives (1992)

19-year-old Juliette Lewis plays a precocious college student who pursues married college professor played, of course, by Allen. Because really, what nubile young co-ed wouldn't be insatiably drawn to a virile hunk of man-flesh like Woody? (Concurrent with the film's release, the ugly tabloid saga of his relationship with Farrow's adopted teenage daughter, Soon-Yi Previn, plays out in the press.)

Mighty Aphrodite (1995)

Woody plays matchmaker for his adopted son's mother, a prostitute/porn star played by Mira "Did I mention I went to Harvard?" Sorvino. Academy voters, apparently thinking Sorvino's hilariously over-the-top accent was intentional, award her an Oscar.

Deconstructing Harry (1997)

In perhaps the most cringe-inducing moment of his career, Allen lays his wrinkled lips on Leaving Las Vegas star Elisabeth Shue. Which might explain why Shue ultimately chose to ditch Hollywood to pursue a career in nursing.

Sweet and Lowdown (1999)

Sean Penn stands in for Allen as a gifted, narcissistic jazz musician who splits his time between a bookish Uma Thurman, a childlike Samantha Morton, and various hookers. And he's the good guy.

The Curse of the Jade Scorpion (2001)

Still considering himself viable as a romantic leading man, Allen casts himself opposite Helen Hunt, Charlize Theron and -- my personal favorite -- Showgirls babe Elizabeth Berkley. Chastised by critics for the implausible casting, he wisely opts to use Jason Biggs and Will Ferrell as surrogates in 2003's Anything Else and 2005's Melinda and Melinda, respectively.

Scoop (2006)

Allen's first collaboration with Scarlett Johansson. All of 20 years old, Johansson is courted by 37-year-old Hugh Jackman -- with Woody thankfully playing the wing-man.

Vicky Cristina Barcelona (2008)

Javier Bardem's refreshingly un-Allen-like character romances Johansson and Cruz simultaneously. Practically ancient at 23, Johansson's days as Allen's muse (a label she vigorously opposes) appear numbered.

Whatever Works (2009)

Curb Your Enthusiasm's Larry David serves as Allen's proxy in a comedy about a "May-December romance" with 20-year-old Evan Rachel Wood. David is a fresh-faced 61.