The 12 Most Age-Inappropriate Romantic Pairings in Woody Allen’s Career

In recent years, Woody Allen has been known for his tendency to cast young actresses as love interests for much older men. While his pairings were mostly age appropriate until the early ‘90s (with the obvious exception of “Manhattan”), the creepiness factor has shot upward in recent years, from Larry David romancing Evan Rachel Wood in 2009’s “Whatever Works” to Emma Stone’s recent pairings with Colin Firth and Joaquin Phoenix (although Allen’s latest film, “Irrational Man,” which stars 26-year-old Stone opposite 40-year-old Joaquin Phoenix, is actually pretty tame compared to some of his other outings). Here’s a look at the most egregious romantic pairings from throughout Allen’s career.

Manhattan (1979)
Pairing: Woody Allen (43), Mariel Hemingway (17)
Age difference: 26 years

In his iconic 1979 romance, Woody Allen romances a 17-year-old girl, played by Mariel Hemingway. In a Vanity Fair piece this year, Hemingway detailed how Allen tried to seduce her as a teenager.

Husbands and Wives (1992)
Pairing: Woody Allen (56), Juliette Lewis (19)
Age difference: 37 years

Allen's character leaves his wife Judy (played by Mia Farrow) and embarks on an unhealthy flirtation with his student, Rain (played by Juliette Lewis). The film came out right around the time Allen left Farrow for a relationship with Farrow’s adopted daughter Soon-Yi Previn. (Allen and Soon-Yi have now been married for 18 years.)

Mighty Aphrodite (1995)
Pairing: Woody Allen (59), Helena Bonham Carter (29)
Age difference: 30 years

Pairing: Helena Bonham Carter (29), Peter Weller (48)
Age difference: 19 years

Pairing: Woody Allen (59), Mina Sorvino (28)
Age difference: 31 years

Allen’s take on “Pygmalion” is full of age-inappropriate pairings. Woody Allen’s wife is played by Helena Bonham Carter. Allen’s character then becomes obsessed with and sleeps with a prostitute played by Mira Sorvino. Helena Bonham Carter, meanwhile, embarks on an affair with her colleague (Peter Weller).

Deconstructing Harry (1997)
Pairing: Julia Louis-Dreyfus (36), Richard Benjamin (59)
Age difference: 23 years

Pairing: Judy Davis (42), Woody Allen (62)
Age difference: 20 years

Pairing: Woody Allen (62), Elisabeth Shue (34)
Age difference: 28 years

Pairing: Elisabeth Shue (34), Billy Crystal (49)
Age difference: 15 years

The 1997 film has an older cast than some of Allen’s films, but the women remain much younger than their male counterparts, as is par for the course in Hollywood. In the film, writer Harry Block (Allen) is romantically linked to Lucy (Judy Davis) and Fay (Elisabeth Shue). Fay, meanwhile, has left Harry for Billy Crystal. Within the novel Harry is writing, a woman named Leslie (Louis-Dreyfus) is sleeping with her sister’s husband (Richard Benjamin).

Sweet and Lowdown (1999)
Pairing: Sean Penn (39), Samantha Morton (22)
Age difference: 17 years

In the 1999 rom-com, Sean Penn plays a jazz guitarist named Emmet Ray who falls in love with a mute woman, played by Samantha Morton.

Small Time Crooks (2000)
Pairing: Woody Allen (64), Tracey Ullman (40)
Age difference: 24 years

In the 2000 film, Woody Allen’s wife, played by Tracy Ullman, is 24 years younger than he is.

Hollywood Ending (2002)
Pairing: Woody Allen (66), Debra Messing (33)
Age difference: 33 years

Pairing: Woody Allen (66), Tea Leoni (36)
Age difference: 30 years

In “Hollywood Ending,” Val Waxman (Allen) has a girlfriend and an ex-wife who are both much younger than he is: Lori (Debra Messing) and Ellie (Tea Leoni).

Scoop (2006)
Pairing: Scarlett Johansson (22), Hugh Jackman (37)
Age difference: 15 years

Posing as Jade, Sondra Pransky (Johansson) dates Peter Lyman (Jackman), whom she suspects of being an infamous killer.

Whatever Works (2009)
Pairing: Larry David (61), Evan Rachel Wood (21)
Age difference: 40 years

Larry David plays a retired professor who romances and marries a 21-year-old runaway, played by 21-year-old Evan Rachel Wood.

You Will Meet A Tall Dark Stranger (2010)
Pairing: Anthony Hopkins (72), Lucy Punch (32)
Age difference: 40 years

In the 2010 Spanish-language film, Alfie (Anthony Hopkins) leaves his wife and marries a young prostitute (Lucy Punch).

Magic in the Moonlight (2014)
Pairing: Emma Stone (25), Colin Firth (53)
Age difference: 28 years

The romantic-comedy follows the dalliances of misanthropic illusionist (Colin Firth) who falls in love with a young mystic (Emma Stone).

Irrational Man (2015)
Pairing: Joaquin Phoenix (40), Emma Stone (26)
Age difference: 14 years

In his most recent outing, Joaquin Phoenix’s philosophy professor enters into a relationship with one of his students, played by 26-year-old Emma Stone.

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