When Valentine's Day rolls around, it's time for a rundown on my favorite romantic films. As always, remember that romance, like beauty, is in the eye of the beholder. What's romantic to me may not be even slightly so to others. Some traditional romantic movies I enjoy and others put me to sleep -- hardly a state in which romance (other than the dream variety) can take place. And, as a man, I like my movies to be about something in addition to the romantic stuff. So, with the possible exception of the most recent two films on this list (see Part III), none of these are what anybody would call "chick flicks." Pardon the sexism, and to each his, or her, own.

First let's take a look at some films made before 1945.

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The Thin Man (1934)
The first of the charming William Powell/Myrna Loy vehicles based on the Dashiell Hammett novel. Funny rather than sappy, which you'll soon discover is one of my most important requirements in a romantic comedy. Watch all of the films in the series, and if you and your significant other don't start talking to each other like Bill and Myrna, I'll be surprised.
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It Happened One Night (1934)
It doesn't get any better, or funnier, than Clark Gable and Claudette Colbert. The first time a movie won Oscars for Best Picture, Best Actor, Best Actress, Best Director, and Best Screenplay.
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Mr. Smith Goes to Washington (1939)
I realize this isn't widely thought of as a "romantic" movie, but the development of the relationship between Jimmy Stewart and an adorable Jean Arthur, presented in the inimitable Capra style, qualifies it as a romantic comedy in my book. If you like the romantic elements in Mr. Smith, you'll also enjoy You Can't Take it With You, made the previous year by the same director and with the same stars.
Buy Mr. Smith Goes to Washington Posters

The Philadelphia Story (1940)
How could a film possibly miss when it involves a romantic triangle with Cary Grant, Jimmy Stewart, and Katharine Hepburn? It can't, of course. For you fans of musicals, not to mention Grace Kelly, Frank Sinatra, and Bing Crosby, it was remade in 1956 as High Society, but the original is still the best.
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The Shop Around the Corner (1940)
Ernst Lubitsch directed and Jimmy Stewart and Margaret Sullavan starred as the clueless pen pals in this delightful romantic comedy, remade 58 years later as You've Got Mail, starring Tom Hanks and Meg Ryan. You may also enjoy the 1949 version, starring Judy Garland and Van Johnson, called In the Good Old Summertime. I'll leave it up to you to decide which you like better; the email gimmick makes for a faster-moving plot, but the other two are charming, old-fashioned, and well-acted by four of the best in the business.
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Ball of Fire (1941) and Meet John Doe (1941)
Gary Cooper and Barbara Stanwyck made both these films in the same year, and even if you think Cooper is the worst actor ever born (he's not), Babs plays off him perfectly in both films, as he plays the straight man in one and the clueless dope in the other.
Buy Ball of Fire and Meet John Doe Posters

Casablanca (1942)
If I did have to rank these films, this one would come first. I shouldn't have to tell you why. If you haven't seen it for some reason, don't wait until V-Day.
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To Have and Have Not (1944)
Bogie and Bacall, together for the first time on film, and together forever in real life. The off-screen story is even better than the one in this film, but it's still a good tale, and has that great speech about how to whistle.
Buy To Have and Have Not Posters

Part I

Part II - 1946-1960

Part III - 1961-1989

Other Classic Movie Checklists that you'll enjoy.