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The 20 May-Decemberiest Romances in Film

By Dustin Rowles | Posted Under Seriously Random Lists | Comments (64)

Jack_Nicholson_og_H_138073a.jpg

Last week’s mention of Aaron Johnson and Sam Taylor-Wood’s romantic relationship actually got me thinking about May-December romances in film, in general. Specifically, the disparity between a couple’s real-life age, and I sort of wondered just how many May-December romances are barely even mentioned, especially between an older man and younger woman.

Below, I give you the 20 greatest disparities between a romantic couple’s real-life age — or at least, where a mutual sexual relationship is involved (technically, I should exclude Lolita, as legally, an underage girl cannot give true consent. But I didn’t). I tried to avoid movies where the romance was too tertiary to matter much, and I also excluded Woody Allen films. Otherwise, we’d be here all night.


1. Harold and Maude (Bud Cort, Ruth Gordon): 52 Years

2. Poison Ivy (Drew Barrymore, Tom Skeritt): 42 Years

3. Entrapment (Sean Connery, Catherine Zeta Jones) 39 Years

4. Lolita (1962) (James Mason, Sue Lyon): 37 Years

5. Something’s Gotta Give (Jack Nicholson, Amanda Peete): 35 Years

6. Shopgirl (Claire Danes, Steve Martin): 34 Years

7. Lost in Translation (Bill Murray, Scarlett Johansson): 34 Years

8. Lolita (1997) (Jeremy Irons, Dominique Swain): 32 Years

9. The Door in the Floor (Kim Basinger, Jon Foster): 31 Years

10. Sabrina (1954) (Humphrey Bogart, Audrey Hepburn): 30 Years

11. Sunday Bloody Sunday (Murray Head, Peter Finch):30 Years

12. Bulworth (Halle Berry, Warren Beaty): 29 Years

13. The Russia House (Sean Connery, Michelle Pfeiffer): 28 Years

14. Crazy Heart (Jeff Bridges, Maggie Gyllenhaal): 28 Years

15. Happy Endings (Tom Arnold, Maggie Gyllenhaal): 28 Years

16. Last Tango in Paris (Marlon Brandon, Maria Schneider): 28 Years

17. Love in the Afternoon (Audrey Hepburn & Gary Cooper): 28 years

18. The Girl in the Cafe (Bill Nighy, Kelly MacDonald): 27 Years

19. Six Days, Seven Nights (Harrison Ford, Anne Heche): 27 Years

20. Charade (Cary Grant, Audrey Hepburn) 26 years









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Comments

Charade (1963)

Cary Grant
Audrey Hepburn

26 years.

Posted by: BWeaves at July 26, 2010 2:02 PM

What about Bill & Ted? There was probably a 500-year age gap between them and Princess Elizabeth and Princess Joanna.

Posted by: sars at July 26, 2010 2:06 PM

5. Wonder Boys (Michael Douglas, Katie Holmes): 34 Years

Sorry, where was the mutual sexual relationship here? As I recall, she crushed on him and made a couple of unreturned passes - that's it.

Posted by: Another Jen at July 26, 2010 2:11 PM

Were Bill Murray and Scarlett Johannsson romantic in "Lost in Translation"? I didn't get that at all. If really relating to each other without moving to sexual is the criterion then why not include "The Professional": Jean Reno, Natalie Portman. 33 years.

Posted by: PaddyDog at July 26, 2010 2:13 PM

I love you BWeaves. I read down the list thinking, "Hello? Cary Grant and Audrey Hepburn in Charade?!", but you had taken care of it. I feel behooved to add that Sabrina was written specifically for Cary Grant and not Bogart; and I think we can all agree it would have made it a much better and more believable film with A.A. Leach in the lead.

Posted by: Mrs. Julien at July 26, 2010 2:18 PM

Clint Eastwood (Dirt) & Meryl Streeptease (Not quite dirt): The Bridges of Old People Fucking.

SOMETHING OBVIOUS (?)

Sean Connery. For Never Say Never Again they should have called him 00AARP...

Connery v. Catherine Zeta-Jones-Douglas: Entrapment -- 39 years

Sir Sean v. Julia Ormond: First Knight -- 35 years


Maybe they aren't "romance-y" enough, but Sean Connery doesn't dick around with that shit.

Posted by: D-Day at July 26, 2010 2:19 PM

I guess I can see why a woman might be attracted some of these wizened and decrepit old fucks much older men, but Tom Arnold?! There's no excuse for anyone ever being attracted to Tom Arnold. Geez, Maggie. You don't have to take every part you're offered.

Posted by: Tracer Bullet at July 26, 2010 2:22 PM

Did Catherine Zeta-Jones and Sean Connery get busy in Entrapment? 39 years.

Posted by: Mrs. Julien at July 26, 2010 2:26 PM

All right, I'm evolving the list, as I receive corrections and oversights. Charade added, and Wonder Boys dropped (I think I incorrectly remembered something sexual b/w Holmes and Douglas in that). I do think that Lost in Translation counts, as she did get jealous when he slept with another woman, and I think he whispered something really naughty in her ear in the end. The Connery ones: I think they're not romanc-y enough. Maybe I'm wrong?

Posted by: Dustin Rowles at July 26, 2010 2:26 PM

Well, OK. That's two for Entrapment. That's added; Sabrina is dropped.

Posted by: Dustin Rowles at July 26, 2010 2:28 PM

The Connery ones: I think they're not romanc-y enough. Maybe I'm wrong?

Sean is going to double "O" kick your ass!

Posted by: admin at July 26, 2010 2:30 PM

The Russia House -- Michelle Pfeiffer at 32, Sean Connery 64?

Something around a 30 year age difference, I know that.

Posted by: Maryscott O'Connor at July 26, 2010 2:36 PM

Poor Dustin, he created a website that the Accuracy Police can't help but feel the need to help him out with. Sorry man.

Posted by: Mrs. Julien at July 26, 2010 2:37 PM

These ladies have a major mothball fetish.

Posted by: Kballs at July 26, 2010 2:39 PM

and I also excluded Woody Allen films. Otherwise, we’d be here all night.

Good choice. Given the subject matter, if this list were to persist for more than six hours, we'd need to seek medical advice.

Posted by: branded at July 26, 2010 2:42 PM

Not in the top 20, but pretty close:

Autumn in New York (Winona Ryder, Richard Gere): 22 years

That one always grossed me out. But nothing like the Jack Nicholson/Helen Hunt/Amanda Peet pairings. Ewwwww.

Posted by: figgy at July 26, 2010 2:43 PM

I think the Woody-Allen-Worthy list would be most laughable May/December romances. Cary Grant or Sean Connery one can almost believe in. Woody Allen and Elizabeth Shue in Deconstructing Harry? I think not. As I recall that movie had the special honour of providing Billy Crystal as the other side of the triangle.

Posted by: Mrs. Julien at July 26, 2010 2:45 PM

[Winces]
Bella is in high school. Edward is over a hundred. That's a good 90-some years.

God, I'm so depressed now. No one hates me for that more than myself. I need to take a shower and wash these thoughts out of me. There is no reason that should be the first thing to come to my mind.

Must...find...something...cool...to do...to...rebuild...reputation...

Posted by: penelope at July 26, 2010 2:46 PM

Oh, Penelope, that's one of the worst ever. Not only is he 100, he's also a virgin who's probably never even touched a girl's boob. He also spends his time watching her sleep and stalking her by reading other people's minds.

And I too am ashamed to admit that I know that, but it was in the name of research.

Posted by: figgy at July 26, 2010 2:48 PM

Both Twilight and Bill and Ted are accurate in that respect, but this list - as explained above -- is only concerned with real-life ages. Thanks, though.

Posted by: Dustin Rowles at July 26, 2010 2:52 PM

Figgy and Penelope - I'm so embarrassed for you right now.

Posted by: Mrs. Julien at July 26, 2010 2:57 PM

I'll agree with you on Connery,Dustin. I could never figure out what women saw in him. As a young man, he looked oddly effeminate. Now in his gloaming, he just looks creepy. Psst, Sean: Scotsmen and major exposure to strong sun = not a good mix.

Posted by: PaddyDog at July 26, 2010 3:06 PM

Ooooh, it just quite missed the cut:

Ahhhhnold / Olivia D'abo -- Conan the Still-Entertaining Mess -- 22 Years

I also need someone who's good with the later Roger Moore movies which all sucked and I stopped paying attention to. He was born in 1927, so that'd put a bunch of actresses in the upper-20-year-age-gap.

Don't know he slept with in this one: http://www.imdb.com/title/tt0082398/

You opened up a can, Rowles, we'll be at this all night.

Posted by: D-Day at July 26, 2010 3:18 PM

Love in the Afternoon - Audrey Hepburn & Gary Cooper - 28 years. She was often paired with much older male leads, but sweet god, Gary Cooper looked like her great-grandpa. And his character was a playboy. It was... creepy.

Posted by: HeathPie at July 26, 2010 3:39 PM

HeathPie, I was just about to say Love in the Afternoon, but I took me longer to look up the dates and do the math than you did. I'm surprised it was only a 28 year difference. He looked so much older than her in the movie. It was creepy indeed.

Posted by: MH at July 26, 2010 3:57 PM

Boy, oh, boy, I can't wait to get old! Best believe, myjetski's gonna be a silver fox, a gray wolf, perhaps a sexy Santa. Ho ho ho ho ho.

(Mrs. myjetski is somewhere rolling her eyes right now.)

Posted by: myjetski at July 26, 2010 4:01 PM

Just missed -- Clark Gable (60) and Marilyn Monroe (35), The Misfits, 25 years.

And I'm not sure if they ever got busy, but what about Peter O'Toole (74) and Jodie Whittaker (24) in Venus, 50! Can anyone confirm or deny?

Posted by: sansho1 at July 26, 2010 4:04 PM

Also just missing -- Kevin Spacey (45) and Kate Bosworth (21) in Beyond the Sea, 24 years. This was creepy in it's own special way though, as Spacey was playing a 25-year-old Bobby Darin.

Posted by: sansho1 at July 26, 2010 4:07 PM

Wasn't there a TV movie Pygmalion-derivative that featured Peter O'Toole getting in on with Jodie Foster. EW.

Posted by: Mrs. Julien at July 26, 2010 4:12 PM

Well, great. You knocked off As Good As It Gets now, so my header image makes no sense! (Love in the Afternoon has been added. I think I'd need a second on House Bunny before I can add it, Che, just because it's such a small part of a very awful movie that no one wants to remember.)

Posted by: Dustin Rowles at July 26, 2010 4:18 PM

Daddy Long Legs (1955)
Fred Astaire and Leslie Caron; 34 years.

He "adopts" her and she writes him letters for years and years and then he finally agrees to meet her once she's in college and they fall in love. Great movie, if you can ignore the creepiness I just described.

Posted by: MyySharona at July 26, 2010 4:20 PM

oooh! Found another one:

To Catch a Thief
Cary Grant and Grace Kelly, 25 year difference

Can't blame them, really. It's CARY GRANT, for crying out loud.

Posted by: figgy at July 26, 2010 4:30 PM

Whoa, MyySharona. That's kinda gross.

Posted by: figgy at July 26, 2010 4:32 PM

Poor Audrey Hepburn. I just thought of another: Funny Face with Fred Astaire. Also in 1957. She was 28, he was 58, which makes for a 30 year difference.

Posted by: MH at July 26, 2010 4:33 PM

The Big Lebowski (1998)
David Huddleston and Tara Reid; 45 years.

Oh yes, boys and girls, lest we forget the chemistry and $1000-blowjobs of the other Lebowskis, Geoffrey and Bunny.

And how bout a special shout-out to Chloe.

Amanda Seyfriend: 25
Julianne Moore: 50
Liam Neeson: 58

I think this should be 58 years combined...

Posted by: D-Day at July 26, 2010 4:34 PM

7. Lost in Translation (Bill Murray, Scarlett Johansson): 34 Years

Never had a sexual relationship. Friendship level, almost kind of a "mentor" status, really.

Posted by: earthmanjack at July 26, 2010 4:36 PM

Door in the Floor was Kim Basinger and Jon Foster. Which is 31 years.

Posted by: Will at July 26, 2010 5:14 PM

The Mother (2003)

Daniel Craig bones Anne Reid on screen.

She's 34 years his senior.

If you remember the Dr. Who episode that introduced Martha Jones, Anne Reid was the alien old lady vampire with the straw.

Posted by: BWeaves at July 26, 2010 5:24 PM

Wait, that lovely young man in Sunday, Bloody Sunday was named Murray Head?

Posted by: Drake at July 26, 2010 5:25 PM

Uh, Michael Douglas and Gwyneth Paltrow in A Perfect Murder (aka Dial M for Murder)? 28 years.

Also, I thought the Kim Basinger/Door in the Floor movie was the movie I saw, where she's running through the woods and ends up fucking Lukas Haas. But apparently, she's been in two movies fucking inappropriately young guys. It turns out that Lukas Haas in real life isn't all that young, although he was supposed to be a teenager in the movie, and it really was pretty creepy.

So I submit, for the runners-up list, While She Was Out. 23 years.

Posted by: MM at July 26, 2010 5:51 PM

Sin City (Bruce Willis and Jessica Alba): 26 Years.

Just like Scarlett and Bill, you know they wanted to.

Posted by: Darth Darko at July 26, 2010 6:15 PM

I'm surprised no one's mentioned SAVAGE GRACE. Since my disgust level with that flick is still pretty high, I have no interest in looking up the actual numbers. All I know is that it had Julianne Moore fucking her teenage son. That's more than enough to gross out anyone and leave this little gem of a turd near the top of this list.

Posted by: Barnes78 at July 26, 2010 6:34 PM

marlon brandon?

Posted by: katy the greaty at July 26, 2010 6:54 PM

Can I just say how much I can't stand Helen Hunt?

Posted by: Snuggiepants at July 26, 2010 8:00 PM

I love the SRL. It's the gift that keeps on giving!

Posted by: figgy at July 26, 2010 8:20 PM

Recently I watched the movie "Yes Man" (or is it Yes, Man?) and I could not get past the age difference between Jim Carrey and Zooey Deschanel. The entire movie I kept commenting the romance might be sweet if I were not so creeped out by old(er) man chasing after a young(er) girl. Clocking in at an 18 year real-age difference, with a Ms. Deschanel playing a decidedly younger version of herself (perhaps 22), I couldn't help but feel grossed out.

Posted by: Drix at July 26, 2010 8:31 PM

Father Goose: Cary Grant and Leslie Caron - 27 years.

Posted by: Three-nineteen at July 26, 2010 8:34 PM

Cary Grant was quite the cradle-snatcher, huh...

Posted by: figgy at July 26, 2010 9:15 PM

Clocking in at an 18 year real-age difference, with a Ms. Deschanel playing a decidedly younger version of herself (perhaps 22), I couldn't help but feel grossed out.

Jesus Christ, 18 years? That's the best you can do? And it grosses you out? Jim Carey is 24 years older than I am, and I'd do him. But then again, Sabrina wasn't on this list twice for nothing...

Posted by: SaBrina at July 26, 2010 9:25 PM

Heh... Cradle snatch...

Posted by: SaBrina at July 26, 2010 9:26 PM

Crap, I just realized I spelled Jim Carrey's name wrong. How can I ever face my peers after this?

Posted by: SaBrina at July 26, 2010 9:46 PM

And I'm not sure if they ever got busy, but what about Peter O'Toole (74) and Jodie Whittaker (24) in Venus, 50! Can anyone confirm or deny?

Posted by: sansho1 at July 26, 2010 4:04 PM?

As I recall, they never did. Peter O'Toole's character Maurice was certainly up for it (oh goddamit, that wasn't meant that way), but he died in her arms just after she'd gotten rid of her boyfriend. That would have been a solid #2 otherwise.

Posted by: Uriah Creep at July 26, 2010 10:15 PM

So Maria Schneider was like 52 in "Tango" then? She sure aged well.

Posted by: , at July 27, 2010 12:29 AM

So Maria Schneider was like 52 in "Tango" then? She sure aged well.

Whah?? She was 20 and Brando was 48. I'll bet I'm missing a joke, aren't I? Please tell me. Please?

Posted by: Uriah Creep at July 27, 2010 1:15 AM

.............................
http://www.matchsugar.com/

Searching for a mate is like searching for a house. You know exactly what you want and what you are looking for, but it has to be within your means and what you can afford. here is a website
www.matchsugar.com....it is a dating service for black and white people to find their true love.maybe you will like it.Sign up for free and find your girl or guy.

Posted by: lio at July 27, 2010 3:56 AM

Funny Face, Audrey Hepburn and Fred Astaire, 30 years.

Posted by: Anonymous coward at July 27, 2010 5:10 AM

Buffy was 16 and Angel was over 200, so . . . there ya go.

In the real world, I always got kinda squicked out by Woody Allen and Julia Robert's relationship in Everyone Say I Love You, especially since he gets her by recreating her sex dreams that she told her therapist. (32 years)

Julia Roberts = 29
Woody Allen = 61

Posted by: Rowen at July 27, 2010 6:23 AM

Since Woody has been broached:

Manhattan, Woody Allen (43), Mariel Hemingway (17) = 26 years. And I don't care what anyone says...it wasn't creepy.

Posted by: sansho1 at July 27, 2010 7:20 AM

I'm not saying I wouldn't bang Sean Connery six ways to Sunday, but it is unsettling just how often the older man/younger woman thing shows up.

I think the main difference I'm noticing is when it's an older woman/younger man, it's a major plot point (Harold and Maude, the Door in the Floor...). When it's the opposite, the issue is simply non-existent. No one feels the need to explain why a woman in her 30s would date a man in his 60s. It's been completely normalized.

Posted by: marya at July 27, 2010 8:59 AM

Posted by: Uriah Creep at July 27, 2010 1:15 AM
---
Joke. Brando always looked like he was 80 to me.

Posted by: , at July 27, 2010 10:32 AM

earthmanjack-

a MENTOR STATUS?! WHAT ON EARTH ARE YOU TALKING ABOUT.

Posted by: ashby at July 28, 2010 3:25 AM

Only in a male-dominated industry, with male directors, writers and producers would there be so many pairings of young, beautiful actresses with attractive but aging, past their prime male stars.Most of the pairings are absolutely cringe worthy.

Posted by: jo at July 28, 2010 3:45 AM

Screw Edward/Bella, The Hunger has them beat. Catherine Denueve's character was alive at least through the Roman Empire. She sexually perused a 13ish year old violin prodigy before being forced to settle with Susan Sarandon, 30s. So, roughly 2000+ years difference. Winners.

Posted by: Robert at July 31, 2010 3:33 PM

I don't believe I've seen this said an informative way before. You really have made this so much clearer for me. Thank you!

Posted by: Heriberto Persechino at December 15, 2010 1:35 PM