Parallel Parking

Parallel Parking is one of the most difficult things to do when you're driving. This is something that will get almost anybody nervous, especially during a Driving Test, and would try avoiding. That, or somehow a character can pull off something daring and spectacular doing it.

Less skilled drivers will usually bump into the cars in front of and/or behind the spot they're either entering or leaving.

Examples of Parallel Parking include:

Advertising

There's a Mentos commercial where some jerk pulls into an open parking spot right when Our Heroine wants to leave, sandwiching her in. Cue a Mentos, and a Bright Idea: she recruits the help of some beefy construction workers to pick up her car and ease it out.
- Being a Smart Car, it can easily be done with four average people, beefiness optional. This troper has witnessed one being taken up a set of stairs at his workplace as a prank.

Film - Animation

The spectacular one is done in The Incredibles, when Mr. Incredible lands the van that was launched from a rocket, then skids perfectly into a vacant parallel spot.
Gru from Despicable Me is perfectly able to parallel park, even though his car puts a semitrailer to shame. He deliberately rams into the cars in front of and behind him anyway. 'Cause he's evil.

Film - Live Action

The Blues Brothers: Elwood J. Blues has to be one of the best in history. Able to do an e-brake slide into any spot.
Ace Ventura 2: Li~ike a glove!
After Annie parks in Annie Hall:

Alvy: Don't worry. We can walk to the curb from here.

Using chi powers to parallel park is one of the things Sing wants to promote in Shaolin Soccer.
The bodyguard Tyrone in Snatch, who'd earlier been talked up as a great driver, smashes hard into a van (ironically containing the guy his bosses are looking for) while backing into a space "big enough for a jumbo jet."

"It was at a funny angle."
"It's behind you, Tyrone! When you back up, things come from behind you!"

Live Action TV

One time on The Late Show With David Letterman they had a remote camera watching some 16-year-olds take their driving test. The parallel parking was particularly bad. For that matter, a semi-recurring segment is having interns parallel park outside the Ed Sullivan Theater.
Mystery Science Theater 3000: During the traffic safety film X Marks The Spot, an early scene has a Match Cut of a car fading into a narrow gap between two cars parked curbside. Tom Servo remarks, "Ah, parallel universe parking." The car's driver has to leave the space the old-fashioned way—as Crow puts it, "He uses the Braille system".
A Tosh.0 bit had various stereotypical poor drivers (Asian woman, 15-year-old girl with her learner's permit, etc) try to parallel park a massive Hummer. The only one who succeeded was the girl.
Reese's driving test in Malcolm in the Middle frustrates him to the point that it turns into a low-speed police chase, which continues for hours until he's nearly out of gas, at which point he leads the Lemming Cops round the entire test run, acing every obstacle and finishing with an inch-perfect parallel park. What do you mean it's not awesome?
In Seventh Heaven, Mary couldn't parallel park during the driving test. She resorted to a crying routing on the evaluator to get the license.
On Seinfeld, George actually claims to be really good at parallel parking, he just didn't count on another guy trying to drive into the space front first while he was backing up. A massive, all-night argument begins between the two drivers over whether front-first parallel parking is acceptable in the civilized world.
One episode of Top Gear involved James May and Jeremy Clarkson driving huge classic cars around London to showcase how fantastic (read: impractical) these cars are in the modern day. One of the producer's challenges involved parallel parking in downtown London, which, as it turns out, was impossible for the cars to do as they are, in fact, longer than the parking spaces themselves.

Video Games

This video, from Halo 3. Really, it's possible in any video game that lets you control the vehicles to a similar degree.

Webcomics

In Wapsi Square, Tina breaks her wrist while parallel parking. She runs over it.
In Nobody Scores!, every attempt at parallel parking results in increasingly implausible accidents.

Western Animation

In one old Disney cartoon placed in the wild west, Bruno comes to town as a villain and parallel parks a horse, bumping into those in front and behind him.
A Looney Tunes short titled "Wild Wife" had a Chew Toy woman speedily hit the parked cars in front and back of her twice apiece. This is probably a "woman driver" joke.
Doug's sister Judy once failed to get her driver's license after failing to correctly parallel park. She finally got it right at the end when most of her concentration was on chewing Doug out for having promised she would drive him and Patti somewhere, which was why he needed her to pass in the first place.
Futurama:
- The first episode has Leela saying that she can fly the ship, as long as she isn't asked to parallel park.
- In one episode, Amy complains that she is useless at parallel parking, and then easily drives in since hovercars can just move sideways. She then suddenly moves forwards and back to hit the two cars anyway.
Phineas and Ferb: one episode focuses on Candace practicing this.
- Also comes up in a later episode when Candace is practicing driving with her mom. Candace's neuroses over her brothers, and later some unintended interference from Doofenshmirtz, ends up resulting in her becoming a textbook example of Drives Like Crazy. However, even Candace's mom had to admit that Candace really had parallel parking down.