" The Hustler" (1961)

"Anything can be great, I don't care, brick laying can be great, if a guy knows what he's doing and why, and if he can make it come off."

"Fast" Eddie Felson is a born loser suffering from a winning streak. A young pool shark long on grit and short on honor, Eddie (Paul Newman) drinks J.T.S. Brown bourbon and hustles suckers at billiards. He's an anti-hero who has lived his whole life for this moment: His face-off against pool hall legend Minnesota Fats (Jackie Gleason), who hasn't lost a pool match in 15 years and doesn't intend to pass the torch anytime soon.

"The Hustler" is ripe with character. Eddie — the startup buck — and his mentor-rival Minnesota Fats are only half the story. After all, where would any startup buck be without funding and a work-life imbalance? Enter Bert Gordon (George C. Scott), the financier with a merciless personal agenda and an intolerance for insolence, and Sarah (Piper Laurie), the intriguing yet troubled blonde alcoholic who must compete with a pool cue for Eddie's time and affection.

Director Robert Rossen cast all the typical villains in this film: arrogance, addiction, and money. So many traps and troubles swirl around Fast Eddie that the only relevant question becomes: Which vice will be the first to unravel the cocky pool hustler from Oakland, California?

Initially, it appears Eddie's overindulgence and overconfidence will play the part of sabotage. Shortly after arriving in New York's Ames Billiard Hall, the traveling con man makes the acquaintance of "The Best" — Minnesota Fats — who arrives dressed in a three-piece suit replete with fresh carnation and gold rings. At 8 p.m. they begin playing $200 games before a jeering audience of pool hall regulars. Fats cleans the table, and Eddie lowers his peacock feathers long enough to admire a great player in action: "Look at the way he moves, like a dancer...And those fingers, them chubby fingers. And that stroke, it's like he's uh, like he's playing a violin or somethin'."

At 1:30 a.m., Fats remains ahead. But the game proceeds, and by 8 a.m. Eddie has collected $11,400. Out of respect for Minnesota Fats, Eddie insists the game continue until his mentor deems it over. Perhaps it is J.T.S. Brown speaking when Eddie boasts, "I beat him all night and I'm gonna beat him all day," because the morning progresses into a downward spiral for the young hustler, who stumbles out of Ames Billiards the next evening with empty pockets and a nasty hangover.

On the verge of defeat and poverty, Eddie deposits his possessions in a bus station locker and joins the beautiful and troubled Sarah at a table in the station coffee house. By the next morning, these two lost souls have taken refuge in each other's addictions and insecurities. Eddie moves in and shares with Sarah many nights of drunken self-destruction but very little information about his pool hall identity.

Soon after falling for Sarah, Eddie stumbles into Bert Gordon, a local agent of sorts who slaps Eddie with a harsh criticism of his recent performance against Minnesota Fats:

Bert Gordon: You got talent.
Eddie Felson: I got talent? So what beat me?
Bert Gordon: Character.

After calling him a "born loser," the corrupt Gordon offers to finance Eddie's pool playing and schedule earth-shattering matches in return for 75 percent of the winnings. Eddie initially refuses the offer, but after a painful scuffle with local punks who don't appreciate his hustle, the downtrodden competitor agrees to join Bert for a whirlwind trip to the Kentucky Derby. There, Eddie is to face off against an aristocrat named Findlay (Murray Hamilton) and win back his honor.

The film's climax builds to a frenzy as the road trip goes from bad to worse with the domineering Gordon and the headstrong Sarah bickering and berating each other at every turn. He calls her a trap. She calls him a bastard. And the fight for Eddie's loyalty begins.

Meanwhile, Eddie descends into obsession. He can see nothing but the score and the satisfaction of winning. He neglects Sarah's pleas for help and earns a bad name in Kentucky billiard circles with his self-assurance and boasting. In retrospect, the tragic conclusion to "The Hustler" was a certainty from the outset. Its fate, like that of many modern-day gamblers, was sealed at the first sign of adversity.

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