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Romantic Comedies Done Right
10 of the Most Original Romantic Comedies
John Cryer and Molly Ringwald in Pretty in Pink
Last weekend saw the release of the romantic comedy Something Borrowed, in which a single career woman falls in love with her best friend’s fiancé. As with every other year, 2011 has seen the release of quite a few rom-coms, including No Strings Attached and Just Go With It, with This Means War, Friends with Benefits and What’s Your Number? set for release before the year is out. The genre tends to rehash the same old plots, themes and conflicts again and again. Will the heroine choose her career or her love life? Will she say “yes” to the responsible, respectable suitor or the fun, unpredictable one? She’s [insert age here] and isn’t married yet--she must be totally unlovable! Maybe she should just--gasp--give up on romance altogether!
The romantic comedy genre as a whole gets a bad rap, but there have been some truly good, original rom-coms. For example, there’s John Hughes’ Pretty in Pink, which stars Molly Ringwald as a high school outcast in love with the rich, popular Blaine (Andrew McCarthy) and lusted after by fellow oddball Duckie (John Cryer). Pretty in Pink has all the hallmarks of a great romantic comedy (a simple, universal story, quirky characters, likable actors and memorable dialogue), plus the added benefit of a lip-syncing scene in which Duckie grooves to Otis Redding’s “Try a Little Tenderness.” This year marks Pretty in Pink‘s 25th anniversary, and MovieMaker has been inspired by its example to take a look back at ten unique, clever romantic comedies, from the 1970s to the present, that have set the standard for the genre. Moviemakers take note: We need more smart romantic comedies like the following. . .
Harold and Maude (1971)
directed by Hal Ashby
Normally the thought of a young man in a relationship with a geriatric is woman is, well, creepy, but this movie manages to turn the odd pair of death-obsessed Harold (Bud Cort) and lively septuagenarian Maude (Ruth Gordon, who won the Best Supporting Actress Oscar for Rosemary’s Baby in 1968) into one of the most charming and memorable on-screen couples in movie history. Enhanced by a soothing Cat Stevens soundtrack, Harold and Maude explores the extraordinary bond between the wide-eyed, eccentric Harold and the wise, effervescent Maude. Bud Cort explained the reason the film resonates is that “it reveals so much mystery and truth about the big questions in life.” If you’ve seen the film, you’ll agree with Mr. Cort. If you haven’t, you’re in for an unforgettable treat.
Annie Hall (1977)
directed by Woody Allen
Annie Hall, the 1978 Academy Award winner for Best Picture, was a unique and groundbreaking romantic comedy for its time. However, much of what made this film so special--for example, its use of subtitles and flashbacks, its animated sequence and tendency to break the fourth wall--was not originally intended. Annie Hall started out as a murder mystery (an idea Allen revisited in Manhattan Murder Mystery), but the film really came together in post-production, after a great deal of original footage was cut and re-shot to focus on the relationship between Alvy (Woody Allen) and Annie (Diane Keaton). Knowing that this iconic romantic comedy could have been a very different film makes one appreciate it all the more.
Tootsie (1982)
directed by Sydney Pollack
Along with Some Like It Hot, Tootsie (which was nominated for the Academy Award for Best Picture in 1983) is considered one of the two best gender-bending romantic comedies ever made. As hilarious as this film is, director Sydney Pollack said that the actors never played their scenes for comedic effect: “No one ever laughed during the shooting of any scenes of the film.” While out-of-work actor Michael’s (Dustin Hoffman) physical transformation into his alter ego Dorothy brings the laughs, the heart of this film lies in Michael’s internal transformation. As Michael tells Julie (Jessica Lange, who took home the Best Supporting Actress Oscar for this film), “I was a better man with you as a woman than I ever was with a woman as a man.”
When Harry Met Sally (1989)
directed by Rob Reiner
At the beginning of When Harry Met Sally, Harry (Billy Crystal) says “Men and women can’t be friends because the sex part always gets in the way.” But Harry and Sally (Meg Ryan) do become friends, and they come to discover that love is not a product of instant attraction, but something that grows over time. They learn each others’ eccentricities, opinions and tastes, and they come to love each other despite them. Norah Ephron received an Academy Award nomination for her script, but she’s the first to admit that not everything in the film was scripted. Some of the greatest moments, like the infamous fake orgasm scene, were improvised or suggested by the actors.
Pretty Woman (1990)
directed by Garry Marshall
There aren’t many romantic comedies in which the heroine is a prostitute. In this Cinderella story, Vivian (Julia Roberts), the hooker with a heart of gold, is so endearing that we want to see her better her life and win over her Prince Charming, Edward (Richard Gere). It’s hard to believe that Roberts wasn’t the first (or second, or third) choice to play Vivian, the role that earned her her second Oscar nomination. The original script was much darker and didn’t appeal to actresses like Meg Ryan, Sandra Bullock and Sarah Jessica Parker, who were only a few of the actresses considered to play the part. Marshall, Gere and Roberts turned out to be a magical team, so it’s no surprise that in 1999 they reunited to make another romantic comedy, Runaway Bride.
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COMMENTS | POST A COMMENT 
- Comment by Liz on 5/21/11 at 10:35 am
I haven’t seen some of the older films that you have included (like Tootsie) but I agree with you in the sense that we need more of these movies. I recently saw a special on John Hughes and how his movies were warmly welcomed by the public because he insisted on including characters that would relate to REAL life. Hopefully we will see more decent movies like his.
- Comment by Yassmin on 5/26/11 at 10:27 am
It is amazing to me that you choose 10 most romantic comedies. And not EVEN one film was with people of a different culture. I am biracial so I see color and notice that one half of me is ALWAYS left out. You should watch and then add Brown Sugar to the list.
- Comment by Samantha Husik on 6/16/11 at 8:25 pm
Hi Yassmin,
When creating this list I considered many films but I had to narrow it down to ten, so I’m sorry if your pick for best romantic comedy was not represented on this list. It’s unfortunate, but in researching for this list I found that there are not many romantic comedies that focus on people of different races/cultures (do something about this - go make a romantic comedy about the cultures you feel aren’t acknowledged in film). By the way, I love Brown Sugar - I own it - but the fact of the matter is that it has not furthered or put a spin on the romantic comedy genre, which is what this list is about.
Thanks for your comment.
-Sam
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