10 movies that feature older women with younger men

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THE GRADUATE, from left, Dustin Hoffman, Anne Bancroft, 1967 — Dustin Hoffman and Anne Bancroft in 'The Graduate'. Photo:
Courtesy Everett Collection

There's a lot to unpack in movies that center around May-December romances featuring a man as the younger — and sometimes inexpert — lover.

Some films present the tryst as illicit; others don't bat an eye. There is also, of course, the inescapable reality that these relationships are treated as novel, while it's often the standard in Hollywood when the ages of the characters getting intimate are reversed.

Nonetheless, there are great movies that handle these pairings with care and successfully mine their emotional depths, as Mike Nichols did in what is maybe the best-loved movie in this mold, The Graduate. (Though, there was only a six-year age difference between the film's leads in real life.)

Below, dig into 10 great films that feature a romance between an older woman and a younger man.

10. Adore (2013) — Lil and Tom; Roz and Ian

Robin Wright and Naomi Watts in 'Adore'. Matt Nettheim

Dating your best friend's son would probably strike most adults as a no-no. But that's not the case for Naomi Watts' Lil and Robin Wright's Roz, best friends who both strike up affairs with the other's sons in this adaptation of Doris Lessing's 2003 novella The Grandmothers.

9. Notes on a Scandal (2006) — Sheba Hart and Steven Connolly

Cate Blanchett and Andrew Simpson in 'Notes on a Scandal'. Everett Collection

Cate Blanchett's free-spirited art teacher Sheba Hart sleeps with a 15-year-old student (Andrew Simpson), but it's her friendship with a nosy co-worker that leads to her ending up arrested for the affair. The lesson: Keep your underage trysts a secret from Judi Dench.

8. Class (1983) — Ellen Burroughs and Jonathan Ogner

Jacqueline Bisset and Andrew McCarthy in 'Class'. Everett Collection

Homeroom gets real awkward when high schooler Jonathan (Andrew McCarthy) discovers that the older woman he's been seeing — played in all her feathered-hair glory by Jacqueline Bisset — is mom to his best pal Skip (Rob Lowe).

7. Bull Durham (1988) — Annie Savoy and Crash Davis; Annie Savoy and Nuke Laloosh

Susan Sarandon in 'Bull Durham'. Everett Collection

Minor-league baseball players Crash (Kevin Costner) and Nuke (Tim Robbins) find themselves under the spell of sexually vivacious fan Annie (Susan Sarandon), who knows her way around the bases.

6. Sunset Boulevard (1950) — Norma Desmond and Joe Gillis

Gloria Swanson in 'Sunset Boulevard'. Everett Collection

In Billy Wilder's classic Hollywood noir, faded silent-film star Norma Desmond (Gloria Swanson) falls in love with newbie screenwriter Joe Gillis (William Holden) but ultimately kills him when he serves her a reality check.

5. American Pie (1999) — Stifler's Mom and Finch

Jennifer Coolidge in 'American Pie'. Vivian Zink

The term "MILF" was barely an idea until Jennifer Coolidge stole the show (and Eddie Kaye Thomas' character's virginity) in this teen raunchfest as Stifler's buxom mom, quickly becoming every teenage boy's dream. (We'll leave it to your imagination what kind.)

4. How Stella Got Her Groove Back (1998) — Stella Payne and Winston Shakespeare

Angela Bassett and Taye Diggs in 'How Stella Got Her Groove Back'. D. Stevens

If you're a successful but single businesswoman like Stella (Angela Bassett), getting your mojo back isn't hard when you go on a first-class vacation to Jamaica and attract a short-shorts-wearing Taye Diggs.

3. To Die For (1995) — Suzanne Stone and Jimmy Emmett

Nicole Kidman in 'To Die For'. Shane Harvey

Nicole Kidman is a comedic marvel as a local weather reporter so obsessed with becoming a famous news anchor that she seduces a trio of teens, including one played by Joaquin Phoenix, and persuades them to murder her husband (Matt Dillon), whom she thinks is holding her back.

2. Harold and Maude (1971) — Maude Chardin and Harold Chasen

Bud Cort and Ruth Gordon in 'Harold and Maude'. Everett Collection

Somehow this dark comedy manages to make a May-December romance between a 79-year-old eccentric (Ruth Gordon) and a death-obsessed young man many decades her junior (Bud Cort) more charmingly offbeat than creepy.

1. The Graduate (1967) — Mrs. Robinson and Benjamin Braddock

Anne Bancroft and Dustin Hoffman in 'The Graduate'. Everett Collection

Anne Bancroft's Oscar-nominated Mrs. Robinson easily holds the title of cinema's ultimate hot mom, thanks to the actress' combination of pathos, blazing sexual magnetism, and sphinxlike expressions in The Graduate. Yes, Benjamin (Dustin Hoffman), she was trying to seduce you.