Look Ma, No Plane

It has been shown in movies again and again that anyone who can fly in an unusual way (whether it be a superpower or just some nifty invention) will fly very close to passenger aircraft, which will either A) annoy those on the plane or B) scare the crap out of those on the plane. Sometimes they'll only be seen by one passenger; usually either a kid who tries in vain to get his parents to look, or a lone alcoholic who stares bemusedly at his miniature of Scotch.

A variation is that, if it is a military aircraft instead of a jetliner, the pilot is likely to demand identification and/or attack.

Probably every flying superhero has done it at least once. Female ones occasionally blow kisses at or otherwise flirt with the pilots. Be careful of the plane's engines, though.

Comics

 * In PS238, Captain Clarinet starts out with a pathological fear of flying, due to having repeated nightmares of being sucked into a jet-engine. It doesn't particularly improve matters when Zodon "helpfully" reminds him that his invulnerability ensures that, should that happen, he'd come out on the other side unscathed... while the plane plummets to the ground in flames with the passengers aboard. ... And then Zodon plays a "practical joke" on him that results in it happening in real life. It backfires spectacularly in that it ends up curing the good captain of his phobia instead of compounding it when is forced to use his flight to put the damaged plane down safely.
 * In the comic Lucifer, the imp Gaudium uses this technique to get from London to New York. To be fair, Gaudium's wings are shorter than his arms and his best flying speed is only a bit faster than a human can walk, so hitching a ride on a commercial jet is practical.
 * In the comics, Spider-Man swings by helicopters all the time. In the game of the second movie, you end up chasing one... if you go too close to the rotors, exactly what you'd expect happens.
 * In one Calvin and Hobbes storyline, Calvin thinks a motorized propeller beanie will let him fly, complete with fantasy sequence where he waves at a plane. Another Sunday fantasy has his parents letting him drive the car, and he drives so fast he breaks the speedometer, goes airborne and passes a jet.
 * Rogue does this in the X-Men comics, buzzing Air Force One and giving ol' Ronnie Reagan a thrill. She does it again in the first issue of her limited series, this time planting a kiss on one of two fighter jets.
 * Inverted in Miracleman, where the title hero (who can fly) takes a plane in his superhero form to meet his enemy Emil Gargunza in Argentina.
 * A 1970s Avengers comic has the title heroes engaged in a battle against Thanos's starfleet. The heroes are flying around in small, vaguely Star Wars-ian ships, but Thor is flying around smashing apart enemy ships under his own power!
 * When Skalman's balloon outperforms a passenger jetplane, the pilot and co-pilot wonder why they are having the same hallucination.
 * Inverted in a Far Side comic: a flock of geese are keeping pace with a passenger jet, and one looks over and sees another goose riding in comfort in the plane, making faces at the others through the window.

Films -- Animation

 * In The Incredibles, the folly of doing this is shown during the "no capes" montage in which a female hero flying by a jetliner and waving at a kid is sucked into the engine when her cape gets caught.
 * In the opening scene of the first Jimmy Neutron movie, Jimmy gets chased by fighter jets while flying his rocketplane. He waves to the pilots and shouts "Nice antiques!"

Films -- Live Action

 * In the second Fantastic Four movie, the Human Torch flies next to the plane in which the rest of the Fantastic Four is flying, annoying the Thing. Yes, you read that right, the Fantastic Four were flying on a ordinary, mundane plane. Johnny had told them, "I don't fly coach."
 * In Superman: The Movie, Superman does this with Air Force One, to save it from crashing.
 * Iron Man (the 2008 movie) is a example of the "fight military aircraft" portion of the trope. And it is awesome.
 * Though actually, Tony unknowingly invaded USAF training space. When Rhodey tries to contact him, he at first lies that he's "driving with the top down", but then admits to be flying in a rocket-powered suit of armor so his men won't shoot him out of the sky.
 * A common sight in daikaiju movies with flying creatures.
 * The Rocketeer did this. It would have looked cooler if there wasn't a hiccup with his rocket pack just then.
 * More like he was still figuring it out - he hit the starter on his jetpack on his helmet!
 * There's a hilarious bit at the end of Flubber using the little boy Running Gag that has been going through the whole movie.
 * During the climax of Addams Family Values, the baby somehow gets catapulted high enough to come eye-to-eye with a commuter plane... specifically, the one that's currently flying the Alpha Bitch and her family home from the disaster that was summer camp.

Live Action TV

 * The Twilight Zone episode "Nightmare at 20,000 Feet" starring William Shatner is the ultimate "scared passenger" example, and one of the few that can be said to be evil. This example also is true for The Movie. A remake of this episode used John Lithgow as Shatner's character. 3rd Rock from the Sun worked in a double Shout-Out when one episode had Dick Solomon (Lithgow) claiming to see something on the wing of the plane, and a later one has the previously-only-mentioned Big Giant Head (Shatner, of course) gets off the plane drunk, saying the same thing (with Dick excitedly saying "That happened to me too!") and explaining that the crew gave him liquor to calm him down.
 * According to Shatner himself, his children would ask him to try this with cabin crew on Real Life flights. Mostly, the crews found this amusing. (This Troper would not advise trying this post-9/11, at least unless you are in fact William Shatner.)

Literature

 * Arthur and Fenchurch in So Long and Thanks For All The Fish. They took a somewhat inventive approach to joining the Mile-High Club.

Video Games

 * In the video game adaptation of Harry Potter and The Chamber of Secrets, Harry and Ron nearly collide with a jumbo jet when flying their father's Ford Anglia to Hogwarts.

Manga

 * Zettai Karen Children:
 * Fujiko is riding on a plane, when she suddenly sees her Friendly Enemy Kyousuke (who has both telekinetic and teleporting powers) flying beside the plane window, just to have a little telepathic chat with her. This infuriates her. A mild subversion since he shows himself only to her, hypnotically hiding his presence from other passengers.
 * In Kyousuke's back-story arc, there is a scene where a fighter pilot gets first confused and then annoyed by two (friendly) ESPers, one of them with telekinetic and the other with teleporting ability, showing up on both wings of his plane, to demonstrate him what an ESPer can do in a battle situation. (And to prepare him psychologically for the upcoming practice battle with little Kyousuke.)

Western Animation

 * In the '90s X-Men animated series, Rogue once sat on the wing of a plane when she needed to think, and didn't notice the passengers freaking out.
 * Danny Phantom has phased through at least one plane.
 * Plane Transformers have been getting closer to real planes of late. Usually fighter jets, and there's sometimes a misunderstanding. (Or it's a Decepticon, in which case, they're right to shoot, but it tends to do them little good.)