Skip To Content
JEWISH. INDEPENDENT. NONPROFIT.
The Schmooze

8 May-December Movies To Make You Re-Think Romance

May-December relationships are a staple not just of the new “Six Dance Lessons in Six Weeks” (read our interview with director Arthur Allen Seidelman here but of many classic movies as well. The recent passing of Mike Nichols has brought one of the best to the fore. Here are 8 that will change how you look at Hollywood romance.

1. The Graduate (Mike Nichols, 1967):

This movie tells the story of an aimless recent college grad, Benjamin Braddock (Dustin Hoffman) who is seduced by an older woman, Mrs. Robinson (Ann Bancroft) and then falls in love with her daughter, Elaine (Katherine Ross). It’s on the American Film Institute’s list of the 100 best movies of all time and was selected by the National Film Registry for preservation as a culturally significant film. Here’s to you Mrs. Robinson…

2. The Reader (Stephen Daltry, 2008):

In Stephen Daltry’s drama, a former Nazi prison guard, Hanna Schmitz (Kate Winslet), has an affair with a 15-year-old boy, Michael Berg (David Kross) and then disappears. They meet again when Berg, as an adult law student (Ralph Finnes) observes her war crimes trial, in which she is wrongly convicted.

3. Lolita (Stanley Kubrick, 1962; Adrian Lyne, 1997)

The Vladimir Nabokov novel received two film adaptations. In the 1962 version, with a screenplay by the author and directed by Stanley Kubrick, James Mason stars as Humbert Humbert and 14-year-old Sue Lyons as Lolita, his sexually charged charge. In the controversial 1997 version directed by Adrian Lyne, those roles were played by Jeremy Irons and Dominique Swain, respectively.

4. American Pie (Chris and Paul Weitz, 1999):

Jim Levenstein (Jason Biggs) gets caught romancing the title “character.” Paul Finch (Eddie Kaye Thomas) does better, with Stifler’s mom (Jennifer Coolidge). And that’s just in the first “American Pie,” directed by the brothers Weitz, Chris and Paul.

5. Manhattan (Woody Allen, 1979):

Forty-two year old Isaac Davis (Woody Allen, who also wrote and directed) dates 17-year-old Tracy (Mariel Hemingway). In an interview, Hemingway said that her scene with Woody in front of the camera was her first-ever make out session.

6. Harold and Maude (Harold Ashby, 1971):

Harold Ashby’s black comedy about a young man (Bud Cort) who drifts into a friendship and then romance with a 79-year-old woman, Maude (Ruth Gordon) was a financial failure before becoming a cult favorite. Now the movie is on the American Film Institute’s list 100 funniest movies of all time and was selected for preservation by the National Film Registry.

7. Twilight (Catherine Hardwicke, 2008):

This is definitely the record setter in the category. He’s 109 (Edward Cullen played by James Pattinson); she’s just 17 (Bella Swan played by Kristen Stewart). In his defense, that’s 109 is 18 in vampire years.

8. American Beauty (Sam Mendes, 1999):

The most honored film of the year (eight Oscar nominations and five wins, including best picture, best director for Sam Mendes and best screenplay), “American Beauty” is about a middle-aged man, Lester Burnham (Kevin Spacey) going through a crisis. He obsesses about a daughter’s friend, cheerleader Angela Hayes (Mena Suvari), and has fantasies of her lying in a bed of red roses.

A message from our CEO & publisher Rachel Fishman Feddersen

I hope you appreciated this article. Before you go, I’d like to ask you to please support the Forward’s award-winning, nonprofit journalism during this critical time.

We’ve set a goal to raise $260,000 by December 31. That’s an ambitious goal, but one that will give us the resources we need to invest in the high quality news, opinion, analysis and cultural coverage that isn’t available anywhere else.

If you feel inspired to make an impact, now is the time to give something back. Join us as a member at your most generous level.

—  Rachel Fishman Feddersen, Publisher and CEO

With your support, we’ll be ready for whatever 2025 brings.

Republish This Story

Please read before republishing

We’re happy to make this story available to republish for free, unless it originated with JTA, Haaretz or another publication (as indicated on the article) and as long as you follow our guidelines. You must credit the Forward, retain our pixel and preserve our canonical link in Google search.  See our full guidelines for more information, and this guide for detail about canonical URLs.

To republish, copy the HTML by clicking on the yellow button to the right; it includes our tracking pixel, all paragraph styles and hyperlinks, the author byline and credit to the Forward. It does not include images; to avoid copyright violations, you must add them manually, following our guidelines. Please email us at [email protected], subject line “republish,” with any questions or to let us know what stories you’re picking up.

We don't support Internet Explorer

Please use Chrome, Safari, Firefox, or Edge to view this site.