Woody Allen’s Films Ranked By Age Disparity

What a nice image of a girl and her father!
What a nice image of a girl and her father!

Yesterday, the trailer for Woody Allen’s latest movie, Magic in the Moonlight, was released and everyone who had momentarily forgotten about the director’s historical penchant for young women was instantly reminded of it, all thanks to the star-crossed couple at the film’s center. Set in the 1920s, Magic in the Moonlight, is the story of Stanley—an Englishman who poses as an Asian magician (no, really)—and Sophie—a charming but possibly duplicitous medium. The trailer is Allen in total Midnight in Paris-y form, and features “flirtatious” dialogue like “you’re a very clever little humbug,” that nobody—not even back in the Jazz Age—would have been able to say with a straight face.

But our problem isn’t with the trite dialogue or hackneyed setup. No, our problem is with the fact that the romantic leads in Allen’s film are played by none other than Colin Firth and Emma Stone. Don’t get us wrong! We have nothing against either of these actors. They’re fine! They’re also really, really far apart in age; Firth is 53 years old and Stone is 25 years old. That’s not the age difference of very many romantic couples, rather that’s the age difference of a father and daughter. Or, maybe, a man and his girlfriend’s daughter. Who’s to say, really.

This got us thinking about Allen’s films, though, which, admittedly is not something we’d done in some time. There are those that are notorious for featuring extreme May-December romances (Manhattan, Everyone Says I Love You, and now, Magic in the Moonlight) and those that have less of an age disparity at work (Hannah and her Sisters, Annie Hall), and we wondered if there was any way to gauge the quality of the film based on the chronological difference between the leads. Which, you know, a film’s quality is obviously subjective (unless it’s Curse of the Jade Scorpion because barf), but in ranking Allen’s films from most age-appropriate romances to least, we discovered… well, what exactly? That Allen’s films are almost uniformly better (there is a glaring, Jason Biggs-ian exception) when they’re not simply masturbatory fantasies? That out of almost 40 films only about 10 are even watchable by critical standards? That we get profoundly sad when we realize how many actors we admire have worked with Allen in the last 20 years? All of the above, actually. But you know, check it out for yourself. Here are Allen’s films ranked, by how many squirms they induce.


1) Bananas (1971): 1 year age difference (Woody Allen, 35; Louise Lasser, 36)

2) Another Woman (1988): 1 year age difference (Gena Rowlands, 58; Ian Holm, 57)

3) Alice (1990): 2 year age difference (Joe Mantegna, 43; Mia Farrow, 45)

4) Anything Else (2003): 2 year age difference (Jason Biggs, 25; Christina Ricci, 23)

5) Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) (1972): 6 year age difference (Woody Allen, 35; Lynn Redgrave, 29)

6) Melinda and Melinda (2004): 6 year age difference (Will Ferrell, 37; Radha Mitchell, 31)

7) Interiors (1978): 7 year age difference (Richard Jordan, 40; Diane Keaton, 33)

8) Midnight In Paris (2011): 7 year age difference (Owen Wilson, 42; Marion Cotillard, 35)

9) Take the Money and Run (1969): 8 year age difference (Woody Allen, 33; Janet Margolin, 25)

10) Match Point (2005): 8 year age difference (Scarlett Johansson, 20; Jonathan Rhys Myers, 28)

11) Zelig(1983): 8 year age difference (Woody Allen, 46; Mia Farrow, 38)

12) Broadway Danny Rose (1984)8 year age difference (Woody Allen, 47; Mia Farrow, 39)

13) Sleeper (1973): 9 year age difference* (Woody Allen, 37; Diane Keaton, 28)

14) Love and Death (1975): 9 year age difference* (Woody Allen, 39; Diane Keaton, 30)

15) Annie Hall (1977): 9 year age difference* (Woody Allen, 41; Diane Keaton, 32)

16) Manhattan Murder Mystery (1993): 9 year age difference* (Woody Allen, 56; Diane Keaton, 47)

17) Stardust Memories (1980): 9 year age difference* (Woody Allen, 43; Charlotte Rampling, 34)

18) The Purple Rose of Cairo (1985): 10 year age difference (Jeff Daniels, 30; Mia Farrow, 40)

19)  Blue Jasmine (2013): 11 year age difference (Cate Blanchett, 44; Alec Baldwin, 55)

20) Hannah and Her Sisters (1986): 15 year age difference (Michael Caine, 53; Barbara Hershey, 38)

21) Scoop (2006): 16 year age difference (Scarlett Johansson, 21; Hugh Jackman, 37)

22) Vicky Cristina Barcelona (2008): 16 year age difference (Scarlett Johansson,  23; Javier Bardem, 39)

23) Bullets Over Broadway (1994): 18 year age difference (John Cusack, 28; Dianne Wiest, 46)

24) Sweet and Lowdown (1999): 18 year age difference (Samantha Morton, 21; Sean Penn, 39)

25) To Rome With Love (2012): 20 year age difference (Woody Allen, 77; Judy Davis, 57)

26) A Midsummer Night’s Sex Comedy (1982): 23 year age difference (Mia Farrow, 37; Jose Ferrer, 60) 

27) Crimes and Misdemeanors (1989): 24 year age difference (Anjelica Huston, 37; Martin Landau, 61) 

28) Small Time Crooks (2000): 25 year age difference (Woody Allen, 65; Tracey Ullman, 40)

29) Manhattan(1979): 26 year age difference (Woody Allen, 43; Mariel Hemingway, 17); 9 year age difference (Woody Allen, 43; Diane Keaton, 34)

30) Deconstructing Harry (1997): 26 year age difference (Woody Allen, 60; Elisabeth Shue, 34)

31) Husbands and Wives (1992): 27 year age difference (Woody Allen, 55; Juliette Lewis, 28);  26 year age difference (Sidney Pollack 62; Judy Davis, 36)

32) The Curse of the Jade Scorpion (2001): 28 year age difference (Woody Allen, 66; Helen Hunt, 38)

33) Magic In the Moonlight (2014): 28 year age difference (Colin Firth, 53; Emma Stone, 25)

34) Everyone Says I Love You (1996): 30 year age difference (Woody Allen, 59; Julia Roberts, 29)

35) Mighty Aphrodite (1995): 31 year age difference (Woody Allen, 58; Mira Sorvino, 27; Helena Bonham Carter, 29)

36) Hollywood Ending (2002): 34 year age difference (Debra Messing, 33; Woody Allen, 67)

37) You Will Meet a Tall Dark Stranger (2010): 39 year age difference (Anthony Hopkins, 72; Lucy Punch, 33)

38) Whatever Works (2009): 41 year age difference (Larry David, 62; Evan Rachel Wood, 21)

*changed from 11-year age difference, because I am bad at math

Follow Kristin Iversen on twitter @kmiversen


  1. Interesting summation. Just makes me think he is a guy who has the power to always put young pretty girls with marginally atrractive old geezers, mostly Woody himself. While it may be reality or wishful for most men it is boring for me as a woman.

  2. I think you’ll find, on checking your arithmetic, that the age difference between Woody Allen and Diane Keaton is 9 years, not 11.

    As far as age gaps–remember Mr. Rochester and Jane Eyre? Mr. Knightley and Emma? etc….. (both from novels written by women)

    Or how about Mr. Darcy and Lizzie?–8 years’ difference in THE quintessential novel written by a woman

  3. I am somewhat loathe to add to the sole comment this sad article has generated but….why waste your time writing up an article like this about someone you clearly hate? Seems pretty unhealthy to me.

  4. Why do you keep saying there’s an 11-year age difference between Woody Allen and Diane Keaton? If you do the math you will find that Woody has always been nine years older than Diane.

  5. In midnight in paris Owen Wilson ends up with the young girl in the end. Léa Seydoux is the actress. In 2011 she was 26 and he was 42. 16 year difference.

  6. I’m not sure why anyone would ever be remotely surprised by this. Woody Allen is 35 years older than his wife, who is his former wife’s adopted daughter whom he started having an affair with when she was 21 years old or YOUNGER.


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