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.

Sleepless in Seattle (1993)
directed by Nora Ephron

Nora Ephron’s delightful script, which pays homage to another great romantic film, An Affair to Remember, earned her (along with co-writers David S. Ward and Jeff Arch) a Best Screenplay nod from the Academy in 1994. What’s unusual about this film is that though Sam (Tom Hanks) and Annie (Meg Ryan) get a glimpse of each other at several points, they don’t actually meet until the last two minutes of the movie. There are very few romantic comedies in which the main characters share such little screen time, yet they have so much chemistry that we root for them to (literally) get together. For those of you who would like to see more than a couple minutes of interaction between the lovable Tom Hanks and Meg Ryan, check out Joe Versus the Volcano (1990) and You’ve Got Mail (1998).

The American President (1995)
directed by Rob Reiner

Fact: No one makes politics as entertaining as The American President‘s screenwriter (and recent Academy Award winner for The Social Network) Aaron Sorkin (check out “The West Wing” if you need further proof). Not only is the writing exceptional, but so is the central idea of the film: The President (Michael Douglas) hurts his chances for reelection by falling for an environmental lobbyist (Annette Bening). How many other romantic comedies can you name that are centered around politics? Add to this an all-star supporting cast including Martin Sheen, Michael J. Fox and Richard Dreyfuss and–voilà–instant classic.

As Good as It Gets (1997)
directed by James L. Brooks

Melvin Udall is not a traditional rom-com leading man. In fact, he’s probably one of the most insensitive, impatient, unsympathetic and nutty characters ever written, yet he is strangely endearing, in part because of the great performance from the incomparable Jack Nicholson. Nicholson won the 1997 Academy Award for Best Actor for this performance, while Helen Hunt, who played his love interest in the film, took home the Oscar for Best Actress, making As Good As it Gets the most recent film to win both statues.

Bridget Jones’ Diary (2001)
directed by Sharon Maguire

Bridget Jones is not your typical romantic comedy heroine. She’s a few pounds overweight, a bit vulgar, a tad insecure and a poor judge of character. In other words, she’s human, which is refreshing given that most rom-com heroines are perfection personified. In addition, Bridget Jones’ Diary is a nod to Pride and Prejudice, and it definitely puts a fresh, comic spin on the classic love story. As is often the case with sequels, Bridget Jones: The Edge of Reason (2004) lacked the sincerity and humor of the first film. Hopefully the next Bridget Jones film (yes, they’re planning a third one) will capture the spirit of the original.

(500) Days of Summer (2009)
directed by Marc Webb

What makes this a great romantic comedy? Three words: Animated. Dance. Sequence. In an article for MM [“(500) Days of Summer, Irony and Parentheses“] screenwriter Scott Neustadter wrote that he and co-writer Michael Weber “… always dreamed of writing a romantic comedy like our heroes Cameron Crowe and Woody Allen—one that was relatable and identifiable, where the comedy came from a real place.” Neustadter and Weber certainly succeeded. Like Woody Allen’s Annie Hall, this film effectively uses humor, in addition to devices like flashbacks, subtitles and daydream sequences, to tell the story of the beginning and end of a relationship. We know we’re not going to see a story with a happy ending (the characters’ relationship only lasts 500 days), but we watch anyway because we become invested in the characters and their emotional journeys.

Do you hate/love one of the movies we listed? Did we miss out on one of your favorites? Want to share your favorite pre-1970s examples of original romantic comedies? Tell us in the comments!