The image of a lady in need of rescue could be one of the oldest literary tropes in history. In traditional stories, the Hero has to rescue a woman, one in some kind of danger or "distress" as it were, and her love is part of the big epic prize he gets for winning at the end.
It's such a tired image, and so inherently sexist, that it's largely fallen out of favor and is mostly used as a joke in modern movies. Today, writers have a lot of fun with the "damsel in distress" trope, using it for satire, plot devices, and character development in a subversive way. These are often a satire or parody of the trope in a clever or interesting way, either by flipping the roles or surprising the audience with a different outcome than what was expected.
8 Stardust (2007)
Stardust didn't fare very well at the box office when it was first released, and that was partly due to a bad marketing campaign. It was sold like a serious adventure story instead of the fantasy-comedy that it really was, including kings, princes, wicked witches, and magical gems. It actually counts as a DC movie, adapted from a comic book. Henry Cavill even plays a small part.
There's more than one candidate for the "damsel in distress" label in this movie to the point where it's satirical, and there are moments when they aren't the ones in distress at all. In fact, the main male character Tristan is the one most often in distress. The leading lady, a fallen star named Yvaine and the best candidate for the "damsel in distress" role, uses her own power to save them in the end.
7 Star Wars (1977)
Remember that the original Star Wars was intended as a comedy, taking inspiration from those early Buck Rodgers shows and the like. That's partly why the "damsel in distress" trope is a part of the original script, not only for the modern writing style but also for the laughs.
It's obvious from the beginning that Princess Leia is the "damsel" in this scenario. She's a princess in flowing white gowns crowned with piles of silky auburn hair, and Luke totally falls for it, just like the audience does. However, by the time she's waving a phaser gun around and giving her companions rude nicknames, everyone has realized that they might have been misled.
6 Shrek (2001)
Not so much a parody of fairy tale archetypes but a savage roast of Disney in every possible way, Shrek also has an interesting twist in the "damsel in distress" trope. The animated movie looks at the concept of a "monster" as more of a social construct than something inherently evil.
This story misleads the audience with a damsel that seems painfully typical at first. Fiona check off all the boxes; guarded by a dragon, held in a tower, and asleep (well, sort of) until her true love should wake her with a kiss. She has a secret, however, and on the journey back to her kingdom, the "damsel in distress" trope that has defined her character starts to unravel.
5 Young Frankenstein (1974)
Oh, there's Spaceballs too, which deserves an honorable mention, but this spot goes to another Mel Brooks parody, Young Frankenstein. Rather than lampoon a fairy tale trope, this one takes inspiration from the horror genre, specifically the classics that were popular in the 1950s and 1960s.
There are a few candidates for "damsels in distress" in Young Frankenstein, and none of them are as helpless as the movie thinks they should be. Inge, one of our suspects, actually rescues Dr. Frankenstein most of the time, and Madeleine Khan steals the show as a not-so-distressed Bride of Frankenstein that proudly rocks her new haircut
4 The Rocky Horror Picture Show (1975)
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Hey Janet, don't ask that question out loud, we know you're not. A damsel in distress, that is. One of the main characters of the cult classic The Rocky Horror Picture Show is the sweet, innocent Janet, who's just a normal kid out with her beau, the equally white-bread college frat-boy, Brad.
A flat tire and a visit to a creepy mansion in search of a phone, and Brad and Janet's world is turned upside down. The typical roles they're expected to fill also fall apart when confronted with the visage of the enigmatic and terrifying Dr. Frankenfurter. Janet finds out she's in distress, all right, but it's not the kind anyone expected, especially Brad.
3 Dragnet (1987)
The vintage television show was a serious and gritty cop drama, but the movie based on it sure wasn't. With Tom Hanks and Dan Akroyd in the leading roles, it's going to be a wacky 1980s comedy that makes fun of those things instead. The damsel in distress is here, and she fits in well with the other various archetypes this movie lampoons, including religious leaders, the mean boss, and cops in general.
The case leads our intrepid heroes to save the Virgin Connie Swail (that is actually how she's referred to several times) from a sacrifice at the hands of a ruthless gang. It sounds like the premise of an SNL skit and could very well have been one. Even her clothes are a perfect match to the trope, starting with a wedding dress, and moving on to a pink taffeta nightmare that only a princess could love.
2 The Last Unicorn (1982)
Peter S. Beagle wrote the original The Last Unicorn novel as a fractured fairy tale, and the script he adapted had similar elements. All the fairytale archetypes make an appearance over the course of The Last Unicorn, from the talking butterfly to the wicked witch, and many are touched by bitterness and time.
The tropes in this movie fall apart in the face of reality eventually, which makes this equally sad and funny. Prince Lir, the stereotypical hero, can only see Lady Amalthea as a damsel in distress. He finds out she is neither a damsel nor is she in distress, and as a consequence, they can never be together.
1 The Princess Bride (1987)
Perhaps the most famous fairy tale parody ever brought to the silver screen, The Princess Bride makes fun of every trope in this genre and not just the "damsel in distress." The hero saves the damsel in these stories, but who is the hero in this scenario?
Buttercup, our damsel in distress, is the victim of some wicked satire. First Westley leaves her, then she gets stuck with Prince Humperdink, who tries to have her killed before the Dread Pirate Roberts then whisks her away. It's nice that she gets the stereotypical happy ending, but it goes to show that the life of a damsel in distress is a lot more stressful than it looks.