It’s no secret that shoes play a center role in entertainment. And when those shoes fail, it takes us off guard and makes for memorable moments we'll not soon forget. Shoe malfunctions, breakdowns, glitches and blips really bring life to any story, fiction or non.

1. Cinderella & the Glass Slipper

Oh dear, this heroine would still doing chores out the wazoo without her glass slippers and their famous malfunction! The latest version of Cinderella is not animated and will appeal to a more sophisticated audience. It looks like sophistication is exactly what Disney is aiming for, offering a line of Cinderella-inspired footwear by nine top designers including Jimmy Choo and Salvatore Ferragamo. Stewart Wietzman presents a jewel encrusted bootie for the line especially designed for the modern princess, priced at a cool $3,500 (available at Saks). And here's a pretty hilarious spoof on the new movie from Saturday Night Live. 

2. He Stole My Strappy Sandals!

We can’t discuss famous shoe malfunctions without the girl who brought the name Manolo Blahnik into every woman’s living room. In hindsight, it’s hard to know if Carrie chased more men around NYC or more pairs of shoes. How can we forget a young, bumbling Carrie in Sex In The City’s “What Goes Around, Comes Around” episode. Poor Carrie is robbed and not only are her hand bag (bagette to be exact) and keys stolen, but her favorite pair of designer strappy sandals.

3. Uh, As If!

Who can forget the 1995 cult hit Clueless? From Tai learning to drive to the famous party scene ("rollin' with the homies"), there are so many memorable moments that are so 90's. But do you remember Cher's shoe malfunction? Travis spills Coke onto Cher's satin sandals and she is not too happy about it. 

4. Don't Make Me Drop a House on You

Coveted by the Wicked Witch of the West, Dorothy’s ruby slippers are considered one of the most important film props in the world. And who can forget this amazing bit of 1939 cinemagic? After the house falls on the Wicked Witch of the East, her sister of the West comes for the slippers, and they magically disappear as her feet and legs recoil under the house. Say what?! Can you say "shoe fail" on the part of the Wicked Sisters? In 2011 this crimson pair sold for a whopping $2-3 million dollars and another pair are currently on display at the Smithsonian, one of the most treasured and asked about pieces in their collection.

5. Death by Stiletto

Here's another outrageous 90's movie shoe malfunction to add to the list. Bridget Fonda shines in the "erotic thriller" Single White Female, playing a psychotic character who causes turmoil for her roommate and her fiancé, Sam. At one point, she gets the same haircut and clothes as her roommate and impersonates her in bed with Sam. When Sam threatens to reveal the truth, she gouges his eye out with a stiletto heel, killing him. Yowch. What a way to go.

6. How Do They Walk in These Things?

In this hilarious 1959 classic, two men witness a murder and are on the run from the mob. They cross-dress into an all female band. Problems ensue when one falls for Marilyn Monroe's character, but he can't tell her because he's a "woman". The other is pursued by a rich suitor who is relentless. In the scene below you get an idea of how difficult it must be for a first-time walker in high heels, as the men wobble through the transit station.