Glass Eye

Glass Eyes are effectively a slightly more technologically advanced version of the eyepatch but without some of the pirate overtones. So they often get the overtones of the Eyepatch of Power. This particularly happens if the glass eye is designed to not match the other eye.

However, another common use of the Glass Eye is for comedy. The eye ends up being ill-fitting, constantly rolls around in the head, perhaps falls out and rolls around on the floor, leading to some slapstick runaround. A common variation for comedy purposes is to make the eyes wooden. It's just inherently funnier somehow, though you might get the common courtesy of a joke where the wooden eye is going along with a pirate's wooden legs and wooden arms and wooden... other bits. Mention must also go to the common joke format of Ignore the Disability, where people take great pains to try to not stare at the deformity.

See also Electronic Eyes for when the concept gets a futuristic upgrade with some more exotic connotations.

Anime & Manga

 * The protagonist of Mushishi, not that one can normally notice. It also serves as a constant reminder of the death that awaits him the moment his other eye disappears. At one point he uses it to make an actual eye for someone.
 * In Yami no Matsuei, Muraki's right eye is often drawn slightly wider than his left, adding to his unsettling appearance. No explanation is offered in the anime (aside from the fact that it glows with a weird blue or violet light when he's summoning familiars/casting curses/generally being freakish and supernatural), but in the manga, during a confrontation with Tsuzuki, it falls out, revealing it to be a glass eye.

Film

 * Ragetti in Pirates of the Caribbean has a wooden eye that has a tendency to fall out a lot and/or "splinter something fierce" especially when he rubs it. He wants to spend his share of the treasure to buy a glass one that fits.
 * Big Bad of Last Action Hero has a selection of glass eyes. Some of whom double as bombs. Each of them with different motifs for the iris (such as a Happy Face or a target or a crosshair).
 * Captain Ron from the movie Captain Ron has a glass eye, but he won it in a poker game and it doesn't fit properly, so he usually has it covered with an eyepatch to hold it in. Later in the movie, during a festival, he tries to remove the eyepatch to blend in, but then his eye spontaneously pops out and bounces away. After searching around for a while, he gives up and puts the eyepatch back on.
 * Since it's Kurt Russell playing this character, it could be a comedic Shout-Out to his more famous character, Snake Plissken.
 * The Sons Of Katie Elder has a Lovable Rogue as one of the sons. He has the trick of auctioning off his glass eye in a raffle at a bar in order to get money for drinks.
 * In Gangs of New York, Bill "The Butcher" Cutting out his eye because it offended him when he lost to Priest Vallon in a street fight in early 19th-century New York City. He replaced it with a glass eye... with an American Eagle for an iris. He taps it with his steak knife to emphasize a point. Daniel Day-Lewis did the scene without blinking.
 * In Valkyrie, Stauffenberg wears a cosmetic eye on formal occasions and an Eyepatch of Power on normal ones.

Literature

 * A very creepy version is Mr. Teatime from Hogfather. He has a grey (black in the Film of the Book) glass eye that may actually be a crystal ball. As the author makes clear, though, it's Teatime's real eye which is the scarier, with its pinhole-sized pupil.
 * Mad-Eye Moody's magical eye from Harry Potter adds an aura of mystique around the veteran dark wizard hunter. His eye also has some particularly creepy abilities such as being able to see through things and turn around in his head to watch all behind him, as befits his ever watchful, ever paranoid personality.
 * Wednesday from American Gods has one. Eye itself doesn't play overly siginficant role in plot (though it plays a role) but it's one of clues to Wednesday's real identity. Well, more the fact that he would actually need one, but still...
 * Isaac, from The Fault in Our Stars, has one at the beginning of the book, as a result of a rare form of eye cancer. The eye itself isn't really mentioned except as part of his description.

Live Action TV

 * On Wings, Lowell mentions his grandmother gets a big laugh every year at Thanksgiving when she takes out her glass eye and sticks it in the stuffing.
 * On Red Dwarf, Warden Ackerman has a glass eye. He does wear an eye patch in one episode where it's been stolen, shortly before it's revealed that he's the owner of a glass eye.
 * One of the most powerful Objects from The Lost Room was the Glass Eye. The only way to use it was to wear it.
 * Columbo implies that he (like actor Peter Falk, see Real Life below) only has one functional eye, telling someone who was helping him search for evidence in one crime that "three eyes are better then two".

Tabletop Games

 * Dungeons & Dragons has magical and Magitek versions, the most famous being The Eye of Vecna.

Theatre

 * A running joke in Accidental Death Of An Anarchist involves the fake Inspector pretending to lose a glass eye (he doesn't actually have a glass eye) and everyone else stopping to look for it. It Makes Sense in Context.

Webcomics

 * Catscratch in The Suburban Jungle has a glass eye to replace the one that was, well, scratched out by a cat.

Comics

 * Kabuki- While kabuki is stuck in prison a fellow agent switches her glass eye with a guards. Her eye is smaller so the guards eye falls out every time he bends over. It plays into their escape plan

Video Games

 * In The Secret of Monkey Island, one of the pirates you meet in Scumm Bar has a glass eye. And the fourth chapter of Tales of Monkey Island involves a magical one that can change color to match the eyes of someone.
 * Bitores Mendez, the village chieftan from Resident Evil 4 has one of these, it apparently has some coding in the iris that's used as a key to the castle.

Real Life

 * Sammy Davis Jr. is probably the best known celebrity to wear an ocular prosthesis, about which he was always very unselfconscious and self-deprecating. (Example: In an outtake from a Bob Hope Special, Sammy blows a cue card line and declares, "Hey, I'm sorry -- I only got one eye, and it was lookin' the other way!!")
 * Once during the run of The Brady Bunch, Barry Williams (Greg) told the other Brady kid actors he had a glass eye. When he was called on it, he borrowed one from an optometrist friend of his father and used that to freak out Eve Plumb (Jan).
 * The actor Peter Falk had to have an eye removed as a child, and so had a glass eye for most of his life. This kind of enhanced his performance as Columbo, the master of Obfuscating Stupidity and Perp Sweating, as it gave him a sort of squint where you didn't know if he was looking at you or not.
 * Which led to a Real Life Crowning Moment of Funny - when playing baseball in High School, he slid into home, and was called out. He popped out his eye, handed it to the umpire, and said "You need this more than I do."
 * Sandy Duncan supposedly has a glass eye.
 * Urban legend. She lost sight in one eye after surgery to remove a tumor, but did not lose the eye itself.
 * Nick Griffin, leader of the British National Party, has one due to an accident involving a shot shell on a burning pile of wood.
 * Jack Elam, wonderful character, had a glass eye, which he used to great effect to look stupid or confused.