Hustler

The Hustler is working a Short Con. He has a simple tale, one that a single person can tell. Generally, the hustler is a little down on his luck, and a little less smooth than a Con Man.

Which is why he shows up in so many shows. Let's face it. The smooth guy who is always right, while The Mark is always wrong ... that smooth guy is a little too smooth to be interesting. He is like Marty Stu, on the grift. (See: Boring Invincible Hero.)

Go back to Ash, of Hustle for a moment. Wasn't he more engaging than Danny (Mr. Smooth)?

Not to be confused with the Larry Flynt magazine. If you're looking for The Hustler, a movie about someone pulling this kind of con, see that page.

Anime and Manga

 * Hare from Monster Rancher started off as this, cheating the main characters out of all their cash on his first appearance after he correctly gauged their rather extreme level of gullibility. He later joins the group himself, mostly out of the desire for a bigger challenge and the chance for some fun.
 * Because on its frequent focus on criminals, Monster features several examples - notably, Otto Heckel and Gunther Milch.

Fan Works

 * This work from DeviantART. The not-so-ditzy cheerleader is hustling chess, of all things.

Film

 * Fast Eddie Felson, who screwed the pooch on the hustle so bad that both Paul Newman and Tom Cruise had to do a movie about him.
 * Steve Martin's character in Dirty Rotten Scoundrels is a Hustler, while Michael Caine's is a full-fledged Con Man.
 * Moses Pray and Addie Loggins are a  team of hustlers in Paper Moon.
 * In Duets, Ricky Dean makes a living by traveling across the country and visiting karaoke bars, where he finds the singer with the biggest ego and insults their hobby and their singing voice until they demand that he take the stage himself, usually betting him money that he can't do any better. Since the character is played by Huey Lewis, it goes without saying that they're usually dead wrong. Usually this pays off for Dean, though sometimes it doesn't turn out so well.
 * In the sixth Police Academy movie, Commandant Lassard and another officer enter a tough bar hoping to question everyone, and a shady guy "invites" him to a game of pool, telling another shady guy he's going to "hustle the old cop for all he's got". Unfortunately for the crook, Lassard is much better at pool than they thought, winning easily. The crook nervously asks him what he wants to know.

Literature

 * The Discworld conman Moist von Lipwig is probably too smooth to qualify as a hustler (at least before Vetinari starts boxing him), but deserves mention for one of his personas, a "lack of confidence trickster" named Edwin Streep, whose down-on-his-luck demeanor and inept Find The Lady game are a cover for forgery (none of the money he loses is real) and pickpocketing (once the marks have shown him where their wallet is, they often never have the chance to discover the money is fake).
 * Time Scout: Skeeter Jackson, Chuck Farley, and Goldie Moran are all masters of the short con.

Live Action TV

 * Ash in Hustle.
 * Harry Anderson had a small role on Cheers as this type of character.
 * In one episode of Married... with Children, Kelly was making money hustling pool with Jefferson managing her. Unfortunately, Al ruined what would have been her biggest payout

Toys

 * Hubcap from Transformers Generation 1 is one, even though he's an Autobot. In Transformers: TransTech and Transformers Animated, Jackpot is shown to be one as well, as Hubcap's partner in crime.

Real Life

 * Victor Lustig, a con man that usually sold a fake money-replicating machine by lamenting it can only replicate one 100$ bill every twelve hours and he needed a lot of money ASAP. Gets special mention for pulling that scheme twice on the same person, pulling a hustle on Al Capone in spite of him knowing who he was and selling the Tour Eiffel.. Twice. Taking a bribe from both his victims to assure them it wasn't a scam.