I left Cleveland to get away from His and Her towels, people who call cocktail parties 'pours' and the guy who always breaks it up by wearing a lampshade on his head.
— Time Magazine article on actor Jim Backus, December 15, 1958.
A person getting drunk enough at a party to wear a lampshade as a hat.
It's hard to pin down the origin of this trope. One theory is that the guys get drunk enough to mistake lamps for hat racks; other theories are collected on this web page. The idea of a drunk wearing a lampshade goes back to at least 1945 in the U.S. - and probably even earlier (another article dates it to 1928). If that's true, this trope could be Older than Television. It has also been suggested that this originated as a piece of "dirty" physical comedy: the man puts on the lamp-shade, exposes himself, and asks for someone to "turn him on" using his "switch".
Regardless, the cliche nature of it has turned it into a Dead Horse Trope. It's uncommon to find examples nowadays that aren't parodies of this.
Sometimes the lampshade wearer will say that they're feeling light-headed.
The same effect is sometimes achieved with a traffic cone, though in reality they tend to be too wide and heavy to be practical as headwear. Add to that the fact that they have to be drunk enough to consider stealing the cone in the first place, so cone wearers tend to be drunker than lampshade wearers.
Note, there is another reason you may see someone with a lampshade on their head: the Rule of Funny use as a Paper-Thin Disguise, in order to pretend to be a lamp. This has nothing to do with being drunk.
A Sister Trope to Necktie Headband (what a Japanese Salaryman will do instead).
Not to be confused with Lampshade Hanging.
Note: it is possible to hang a lampshade on Lampshade Wearing. Case in point: "Someone does it at every party, it was only natural."
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Anime and Manga
The Person Formerly Known as Taro Sekiutsu in Sayonara, Zetsubou-Sensei sold his name to an immigrant, and now lives in a cardboard box in the streets, wearing a lampshade as a mask.
Father Goose - a movie about a commander having to take care of a school teacher and her students had a scene in which the teacher accidentally got drunk because of a mistaken belief she was bitten by a snake (long story). He led the rather prim woman to believe she did dance naked with a lampshade on her head.
In Hot Fuzz one of the teens constable Angel arrests for being drunk and disorderly is wearing a traffic cone on his head.
"There are no delusions for the dead. Dying is like waking up after a really good party, when you have one or two seconds of innocent freedom before you recollect all the things you did last night which seemed so logical and hilarious at the time, and then you remember the really amazing thing you did with a lampshade and two balloons, which had them in stitches, and now realize you're going to have to look a lot of people in the eye today and you're sober now and so are they but you can both remember."
One of the students in Wayside School is Falling Down raises a theory that Mrs. Jewls lets Myron do whatever he wants because Myron has a picture of Mrs. Jewls wearing a lampshade, and threatened to show it to the principal unless she allowed him to break the rules. One of the other students then asks how the principal would recognize Mrs. Jewls if a lampshade covered her face.
Roy Blount Jr's 1984 comic essay "What to Do on New Year's Eve - II" discusses this:
"Try it, and you'll see why. A lampshade has prongs that don't fit the human head (might fit a cat's, but a cat would hate it), and there are dead moths in there. Stuck to the sides. But not stuck very securely. You could breathe one into your nose."
In Mash, when Winchester thought he had an accidental marriage, there are pictures (which the audience never sees) of him doing just this.
An episode of Feral TV involved the cast having acquired a large stash of lampshades, which they naturally put on their heads and used as 'helmets' for a Power Rangers spoof.
Mighty Dorky Power Whingers!
Michael Scott in The Office episode "Christmas Party" wears a lampshade at one point during the episode, likely drunk.
Father Ted wears a lampshade in one episode - not out of drunkenness, but to impersonate a stereotypical Chinaman. (How was he to know that there were three Chinese people observing him through the window?)
This was the basis for one of the physical challenges on Double Dare - one partner would have to find poker chips in a bowl of dip and throw them to his partner, who was required to catch them with the lampshade serving as a blindfold.
In the Red Dwarf episode "The Last Day", Lister somehow wakes up wearing a traffic cone ("On a mining ship, 3 million years into deep space") after a night of drunken revelry. Cat Hand Waves it by saying "It's not a good night unless you get a traffic cone."
On one of George Carlin's stand-up albums, he claims that doing impressions of Ed Sullivan is replacing wearing the lampshade at parties.
Brad Paisley's "Alcohol", sung from the POV of alcohol itself, contains the line "And I'll bet you a drink or two / That I can make you / Put that lampshade on your head." Deconstructed in the music video, where "Little" Jimmy Dickens walks onscreen and dons a lampshade in the most deliberate fashion.
The Irish Rovers' song "Wasn't That a Party?" has a variant of this trope.
"Someone took a grapefruit and wore it like a hat."
Jellyfish mentions someone as wearing a "lampshade crown of thorns" in the lyrics of "Joining A Fan Club".
A Far Side cartoon with three teenagers on a couch, surveying a living room which they have obviously carefully tidied, moments before the parents come home... "Play it cool," says one, "they'll never know we've been partying." The deception would be perfect if they were not all three wearing lampshades.
It's definitely appeared in a few different Garfield strips.
It's a prominent recurring feature in The Garfield How to Party Book by Jim Davis.
In Peanuts, Snoopy and Spike have worn lampshades on a couple of occasions.
In Doonesbury, Mark Slackmeyer is bartending a college reunion, and an attendee comes up to the bar wearing a lampshade... before the party has even begun.
Patrick from Sponge Bob Square Pants comes home in one when he arrives home at midnight saying, "That was some party!" when he was supposed to come home earlier and help Spongebob with the baby scallop/clam (long story).
Oddly enough, in "Spongebob Meets the Strangler", SQUIDWARD wore one of these... TWICE.
Judging by his expression, even Larry was impressed by this particular move... TWICE.
Gary also does it in another episode, and SpongeBob is still able to pull the chain attached to the shade and turn off the light.
In one Freakazoid! episode, the villains are at a party for Freakazoid's imminent doom. Invisibo wears a lampshade so you can tell where he is.
In the Looney Tunes short "Norman Normal" (1968) there's a character who wears a lampshade while droningly saying "Approval" over and over.
One of the drunken cats in "Trap Happy Porky," (1945) belting out "On Moonlight Bay" (natch) also wears a lampshade.
In Aladdin, Genie turns himself into a lampshade over Al's head for the line "A girl appreciates a man who can make her laugh."
One episode of Xiaolin Showdown involves the Ring of Nine Dragons, which spits a person into up to nine copies of themself, unfortunately also dividing intelligence among them. When Jack Spicer gets his hands on it, we see one of his clones with a lampshade on his head.
In the episode "Madeline and the Big Cheese" of the Madeline animated series, Danielle and Madeline has to come up with an impromptu way to lull Lord Cucuface to sleep so... well, see the TV.com summary.
Madeline: Psst, Danielle, you be the queen.
Danielle: Me? Queen who?
Madeline: (thinks) AHA! (Puts lampshade over Danielle's head) Queen Lampshade!