To roll a drunk is to find someone who has passed out drunk and go through their pockets looking for valuables. Sometimes the thief will tail a drunk, waiting for them to pass out.
Requiring no skill or courage on the part of the thief, drunk rolling is generally regarded as the lowest form of theft and (in fiction at least) those who practice it are treated as the lowest echelon of the underworld.
In extremis, a hero who is strapped for cash may be forced to attempt this. Expect them to be humorously bad at this, and for hilarity to accompany their attempts.
Related to Robbing the Dead.
Organ Theft could be considered a specific instance of this, where one's organs are stolen while intoxicated.
Needless to say, this does occur in Real Life. The term "rolling the drunks" originated in 19th century New York, when tavern owners would tip off a local gang when a suitably inebriated customer was leaving the premises. The gang would "roll" the drunk into an alley and swiftly and efficiently relieve him of valuables, with possibly a blow to the head if he wasn't already passing out. The gang would pay the tavern owner a percentage of the take for the tipoff.
- Asterix: In "Asterix and the Laurel Wreath", a thief named Habeascorpus and his band of cutthroats attempt this on a couple of seemingly unsuspecting victims. Unfortunately for them, their targets a) aren't drunk, only asleep, and b) are Asterix and Obelix. However, after he and his thugs have all been knocked flat, he invites them to join his gang (which they pretend to go along with, as they're wanted by the Roman authorities and in need of somewhere to hide out).
- A more calculated example than most in a 2020 X-Men comic, where Wolverine deliberately gets Magneto so drunk he passes out (halfway through telling Wolverine they should be friends, no less), and then steals his helmet (which Wolverine needs to defend himself against a mind-controlling villain).
- More than once in Knights of the Dinner Table, B.A. has become frustrated by his players ignoring his carefully-crafted adventure in favour of roaming the alleys of the city attempting to scam easy XP by rolling drunks.
- During Brian's Cattle Punk campaign, Bob's character has his boots stolen by a local outlaw. Bob then becomes obsessed with stealing a pair of boots off a drunk sleeping in the livery stable. He runs into all kinds of problems and this act will keep coming back to haunt him over the course of the campaign.
- In Glamour For Sale, police detective Jim Davis enlists the aid of good-girl Ann Powell, inadvertently involved with bad-girl Peggy Davis, in the investigation of an escort service that thinly disguises such nefarious practices as rolling drunks, blackmail, and extortion.
- In Money Train John and Charlie are transit cops who often pretend to be drunk or high and then foil would-be thieves who attempt to roll them. In one case it backfires on John when a couple of obnoxious women don't just try to roll him, but to take him home with them as well. Grace, a female cop, has to intervene, pretending to be his enraged and equally drunk girlfriend.
- Once Upon a Time in America: In 1918, Noodles and his pals plan to rob a drunk as a truck hides them from a police officer, but they're foiled by Maximillian "Max" Bercovicz, who jumps off the truck to rob the man himself. Noodles confronts Max, but a crooked police officer steals the watch that they are fighting over.
- In Pool of London, the man who takes Johnny to the illegal drinking club later steals his cash while Johnny is passing out drunk.
- Subverted in Scrooged with Eliott Laudermilk. After getting fired by Frank Cross, Elliott spends the night and most of the next day boozing; however, he doesn't get rolled until he passes out from donating blood for money; a homeless guy helps himself to Eliott's cash (and also his coat).
- The first time the street kid Pete is seen in Two Hands he is stealing the wallet of someone passed out in an alley.
- Underworld U.S.A. opens with a 14 year-old Tolly rolling a drunk who has just left a New Years Eve party. He steals the man's wallet and watch before he has to flee from an approaching cop.
- In The Fortress of the Black Cauldron, the drinking contest you can take part in was actually organised by Luci so that she could pickpocket your opponent.
- In Gorky Park, when Renko is looking up past firearms offenses, one of the cases he comes across is a youth who used a wooden replica of a pistol to rob a drunk. Drunks getting robbed would also show up from time to time in the sequels; not surprising, considering that most of the books take place in the Soviet Union and Russian Federation.
- The Great Train Robbery: Eighteen months after the robbery, Agar's mistress is caught in the act of robbing a drunk and informs on Agar to escape imprisonment.
- In Le Mauvais Génie of Countess de Ségur, Alcide steals money from Mr. Georgey after getting him and Julien (his little protege) drunk. He then puts some of the money in Julien's pockets to make him look like the guilty party.
- In The Outsiders, Dally wears a ring that he obtained by rolling a drunk senior.
- In Red Dwarf: Infinity Welcomes Careful Drivers, the introductory chapters on Mimas introduce a pair of homeless drug addicts by the name of Denis and Josie. With Josie completely immersed in Better Than Life, Denis has to provide for both of them, most commonly by stealing from drunken spacers on shore leave: the last decent meal he's had is a slice of pizza nicked from one such tourist two days prior. In the end, this doesn't work out, so Denis resorts to taking some Bliss for Dutch courage and mugging his targets instead — the first of them being Lister.
- In Wyatt by Garry Disher, Wyatt does this to man who is already in the drunk tank. Scooped up when the police did a sweep rounding up the homeless, Wyatt needs to get out of jail before the police check his prints and discover he is wanted. Finding a middle class businessman on a bender who was grabbed in the same raid, Wyatt lifts his ID off while he is passed out. When the police start releasing those who obviously aren't homeless, Wyatt passes himself off as the businessman and walks free.
- Dead Man's Gun: In "The Highwayman", Robert Cosgrove obtains the eponymous gun (and $93 in cash) by rolling Jonathan Barrett—a guest at his boarding house — when he is passed out drunk.
- In The Defenders, Jessica steals a can of beer from a passed-out homeless man on the subway.
- The Murder, She Wrote episode "Smooth Operators". Upon seeing Elliot dumped in the alley, a local homeless man creeps up on him and steals his watch and wallet. He then tries to steal his shoes, but can only get one off due to rigor mortis.
- Bowling for Soup: In "I Think You Like Me Too", the singer initially claims that he got jukebox money from a friendly biker. In one of the later verses, he admits:
That biker guy was passed out on the floor
We took his wallet and the keys to his Harley
And now he doesn't have them anymore
- The old English music hall song "If You Want to Know the Time Ask a Policeman" was about the well-known practice of policemen stealing watches from drunks. A Conservative MP in Thatcher's government, not knowing the background, referred to it as an example of the friendly relationship between the 19th C. police and the working class.
- Les Misérables: In his song "Master of the House," Thenardier cheerfully admits to robbing his patrons when they're too drunk to notice, alongside all his other shady business practices.
Master of the house, keeper of the zoo
Ready to relieve 'em of a sou or two
Watering the wine, making up the weight
Pickin' up their knick-knacks when they can't see straight
- Fallen London: The 'Rob a drunk' storylet allows you to do Exactly What It Says on the Tin.
- Genshin Impact: In one of the roads in Mondstadt region, you may come across an NPC named Greg. If you talk to him, he at first tries to strike a friendly conversation with you, in which you can have a dialog option where you're saying nonsense. But later, one dialog option can make Greg point out that you're actually pretending to be drunk, and he chooses to stop talking with you. He's actually one of the Treasure Hoarders, who you commonly find as enemies.
- Paper Chase: If you drink enough to pass out, when you wake up, all your possessions will be gone.
- In Quest for Glory I, if you drink enough terrible beer or a single Troll Sweat at the bar, you'll wake up outside with no money.
- Subeta's Drunk Carl gives Fetch Quests. Occasionally the items you give him will make him pass out, in which case you get your reward for the quest directly from his pockets. This may happen regardless of what he asked for, which can include bags of coffee grounds, beef jerky, pastries, and boxes of tiles.