Great Classic Films: Date Night

Valentine’s Day is fast approaching, so in the spirit of romance I’ve compiled a list of five classic romantic films. This is my latest installment of Great Classic Films for various occasions and audiences, including my picks for the Fourth of JulyHalloween, Christmas, and Classics for Kids. This list was harder than usual to make because Old Hollywood did romance really, really well. There are dozens of great romantic movies I could have chosen, but I’ve whittled it down to these five suggestions.

So, if you’re skipping Fifty Shades of Grey this Valentine’s Day and need something else to watch, here are my picks of great love stories and classic romantic comedies perfect for date night.

1. An Affair to Remember (1957)

If you want intense romance, grab some tissues and settle in for one of the most romantic movies of all time (ranked #5 on AFI’s list of Greatest Love Stories). Cary Grant meets Deborah Kerr onboard an ocean liner sailing from Europe to New York. They’re both in serious relationships with other people, but love isn’t always convenient! The ship docks in New York, and the lovesick pair make a plan: they will meet in exactly six months at the top of the Empire State Building if they decide to give the relationship a go. (If you’ve seen Sleepless in Seattle, you know this movie!)

Something goes wrong, though, and we are afraid that our couple won’t live happily ever after. I won’t spoil the ending, but it’s amazing, and the whole film is drenched in romance and feelings. Fun fact: This movie is a very faithful remake of Love Affair (1939), starring Charles Boyer and Irene Dunne. In fact, both films were directed by Leo McCarey!

Here’s the trailer, and click here to buy this film. Bonus: You can watch An Affair to Remember on Netflix streaming, and Love Affair on the Movie and Music Network.


2. The More the Merrier (1943)

This film is the romantic comedy, in my opinion. I absolutely love its enchanting combination of goofiness, romance, comedy, and swoon-worthy moments. Plus, it stars my favorite actor and eternal crush, Joel McCrea.

The More the Merrier is set in WWII in Washington, D.C., which is struggling with a housing shortage. An elderly millionaire (Charles Coburn) arrives on business and worms his way into becoming a young woman’s roommate (Jean Arthur). He then sets about finding her a “high-type, clean-cut, nice young fellow.”

He meets Joel McCrea and decides he is the perfect candidate, so he invites him to share his half of the apartment. Naturally, all sorts of hijinks ensue, most of which are hilarious, sexy, sweet, ridiculously romantic, or all of the above.

This is a marvelous movie that gets around Production Code norms in some very creative ways. The pillow talk separated by a wall and the stoop scene are personal favorites. Fun fact: This movie was nominated for Best Picture, and was re-made with Cary Grant as Walk, Don’t Run in 1966, but it can’t compare to the original.

Here’s a clip, and you can read my full review here. And you can buy this great movie here.


3. Roman Holiday (1953)

This movie has a wonderful love story, iconic actors, one of the greatest days ever, and an ending that will make you cry and smile at the same time. Audrey Hepburn plays Princess Anne from an unnamed country on a goodwill European tour. She’s poised and dignified, but she’s also very young, and her royal duties don’t allow much time for relaxation or fun. During her visit to Rome, all the pressure, responsibilities, and exhaustion finally get to her, and the doctor gives her a sedative to help her sleep. But before it takes hold, she sneaks out and wanders the streets of Rome, where a very handsome and very decent American (Gregory Peck) finds her. She doesn’t know that he is actually a reporter planning to use her “Roman holiday” as his big scoop…

This movie is charming, poignant, damn romantic (#4 on AFI’s list of Greatest Love Stories), and overall incredibly delightful. Fun fact: it was Audrey Hepburn’s first Hollywood film, and she won the Oscar for her performance! Here’s the trailer, and here is my full-length review of the film. You can buy this movie here.

4. Casablanca (1942)

This was also one of my Fourth of July picks, but this movie is just so darn timeless and amazing that it works for just about any occasion! If there was an entry for “timeless classic” in a film encyclopedia, it would be Casablanca.

Unlike some other classics that can feel like a chore to watch, and that you “appreciate” but don’t really enjoy, this movie remains gripping, funny, romantic, and crazy-watchable, even seventy-three years later.

The cast can’t be beat: Humphrey Bogart, Ingrid Bergman, Claude Rains, and Paul Henreid, among many other greats. The script is taut perfection, it’s packed with incredible moments, and the love story is one for the ages. Even if you haven’t seen it, you probably know some of its famous lines. “We’ll always have Paris,” anyone?

Rick (Bogart) is an American living in Vichy-occupied but really Nazi-controlled Casablanca, a city full of refugees fleeing Europe. The dream is to get to America through Casablanca via neutral Portugal, but many get stuck in Casablanca indefinitely. Rick runs his nightclub and remains “neutral,” but things get complicated when an old love arrives and needs his help to escape the Nazis.

I cannot emphasize enough what a must-see this movie is. Fun fact: Casablanca ranked #1 on AFI’s Greatest Love Stories, and #3 on the 100 Greatest Movies of All Time list. Here’s the trailer, and click here to buy this classic.


5. The Palm Beach Story (1942)

This film is a grown-up romantic comedy that starts after the happy ending. It’s got a bit more bite than the typical romance, but that makes it more fun.

Witty, goofy, writer-director Preston Sturges brings his trademark snappy dialogue, hilarious, farcical sophistication, and pratfalls to this amazing movie. Joel McCrea (can’t help myself) and Claudette Colbert are married and in love, but money is tight, so Colbert decides to divorce her husband and use her beauty to entice wealthy men to invest in McCrea’s invention.

She is convinced that she’ll be much more helpful to McCrea as a pretty divorcée than as his wife. She sets off for Palm Beach (where the millionaires are, dahling) with McCrea in pursuit. They meet fabulous characters (Mary Astor, and Rudy Vallee, among others) as McCrea tries to get Colbert back and she attempts to fight their powerful love and attraction for each other. You’d think she’d learn not to ask for his help undoing a stubborn zipper on her dress…

Fun fact: Sturges later wrote that this movie was all about his theory of “the aristocracy of beauty,” as demonstrated by the film’s notion that a beautiful woman can get just about anything she wants. He also claimed the story was based in part on his own experiences amongst the millionaires of Palm Beach, writing simply: “Millionaires are funny.”

Here’s the trailer, and you can read my full review here. You can buy this movie here.

I hope that one of these romantic classics strikes your fancy. For more, follow me on TwittertumblrPinterestInstagram at BlondeAtTheFilm, and Facebook. As always, thanks for reading, and Happy Valentine’s Day!

Categories: Comedy, Drama, Romance, Screwball

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20 replies »

  1. Nice list! I am a Jean Arthur fan, so The More the Merrier is a great pick in my book. You also might want to check out another lovely Arthur film, The Devil and Miss Jones, it is terribly charming…..And related to the terrific Palm Beach Story is Midnight, also starring Colbert and Astor, and featuring a very funny performance by John Barrymore. Happy Valentine viewing!

  2. Perfect list! I don’t know how you could restrain yourself to just those five. If I had to pick, I’d be freaking out. (No, Notorious! No, Magnificent Obsession! I forgot Now Voyager! What about…) Interesting fact about An Affair to Remember: when a friend told Cary Grant that the ending made him cry, Cary’s response was “It always does that to me, too.” Just when you thought he couldn’t get any better.

    • Love that Cary Grant story, Michaela! Swoon. I know, Notorious and Now, Voyager were close calls! I think there will definitely be some more “date night” lists coming soon. Classic Hollywood did romance so well!

  3. Good choices. Not sure where I’d put it, but I’d have “I Know Where I’m Going” somewhere in the top 5. The story and setting are beautiful, and while the leads aren’t really glamorous, that makes it more romantic somehow. (I believe that last is also true for Brief Encounter.)

    I’d probably knock out Affair To Remember. I can’t identify with Cary Grant. He’s like the next stage of evolution. I feel like a chimp watching him.

    [SPOILERS] Roman Holiday is wonderful but the princess’ duty is ridiculous. Would Monaco or Liechtenstein or wherever she’s from erupt into civil war if she left to go with Peck? Would the Soviets invade? No. Let them find someone else to cut their ribbons and christen their yachts. If I was her subject, I’d let her marry him so long as she promised to visit us once a year and wave at me. Happy ending for everybody.

  4. Thanks, Syd! I’ve never seen “I Know Where I’m Going;” thanks for the recommendation! And maybe the Princess could have stayed with Peck, but isn’t it so romantic and poignant that she doesn’t? Maybe they met up later when she was older and made it work.

    • Oh it’s very romantic that she doesn’t (The Love That Can Never Be), and if they had shown me the script I wouldn’t have changed a thing. It’s so enthralling that it was hours before it occurred to me to ask why she couldn’t abdicate.

      I would so love to believe that they could get together when she’s older, but after 10 years – and this is the real tragedy – she will be a very dull person.

      There was a joke about the Emperor Franz Josef that he could speak platitudes in 15 languages, but the insult is directed more at the office than the man. Despite Audrey’s new-found maturity at the end of the film, I’m afraid the tedium of the job will soon smother her spirit and charm. Being vague and uninteresting is in the job description, and her mind and personality is bound to reflect this eventually. That holiday was her last and only chance to be a real individual.

      “You are who you pretend to be, so be careful who you pretend to be.”

  5. I’ll be watching WINGS OF DESIRE part of the Wim Wenders Retrospective, Austin Film Society on Valentine’s day.. I can’t see More The Merrier enough…

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