Jake Gyllenhaal as Pilot Kelson in "Highway" (2002)
"Highway" is a 2002 independent drama written by Scott Rosenburg and directed by James Cox. It stars Jared Leto, Jake Gyllenhaal and Selma Blair. Set in 1994, the film opens in Las Vegas with Pilot Kelson (Jake Gyllenhaal), a casino valet.
In 2004, Maguire took up tournament poker. He was tutored by poker professional Daniel Negreanu. Maguire can be seen on ESPN's coverage of the 2005, 2006, and 2007 World Series of Poker Main Event Championship. Moreover, professional poker player Phil Hellmuth said during the June 28, 2007 episode of Poker After Dark that Tobey Maguire had won $10 million by playing poker in Hollywood.
Michael Cera playing poker at Fox Fall Season Launch Event, on 24th October 2005
Andrew Keegan, who attended Poker for Katrina Relief in Los Angeles on 1st December 2005, is good friends with Emile Hirsch, both like playing poker and gambling online
Matt Damon as Mike McDermott in "Rounders" (1998)
"Hard Eight" was originally called "Sydney" and it was Paul Thomas Anderson’s first film. The movie is from a pre-Rounders generation and draws more on the old Vegas poker world.
Gamblers live for the moment, for the next bet and this gilt-edged noir contraption is an enjoyable wallow in life-is-a-game-table existentialism. Our guide in the film is Sydney (Philip Baker Hall), a silver-haired, lone-wolf gambler who invites a drifter (John C. Reilly) to share a cup of coffee with him. Played with a riveting poker face by Philip Baker Hall, he hovers over the action like a gambling wizard: anticipating, self-confident, juggling random tournaments. Writer-director Paul Thomas Anderson crafts a plot of manipulation and chance, in which some zigs and zags are decisive.
Gwyneth Paltrow as Clementine in "Hard Eight" (1996). "Gwyneth Paltrow in her best role yet" -John Anderson, Los Angeles Times.
Sydney (Philip Baker Hall), a mysterious professional gambler, befriends John (John C. Reilly), a young man in trouble, and teaches him the ways of making a living in the casinos of Reno.
Gwyneth Paltrow and Philip Baker Hall in "Hard Eight", directed by Paul Thomas Anderson
Sydney (Philip Baker Hall) is a man who has been gambling for a long time, and knows a lot about the subject, and shares his knowledge with a young man named John (John C. Reilly):Sydney (Philip Baker Hall), a mysterious professional gambler, befriends John (John C. Reilly) and teaches him the ways of making a living in the casinos of Reno.
Paul Newman playing poker in "The Sting" (1973)
After Henry Gondorf (Paul Newman) and John Hooker (Robert Redford) spot Doyle Lonnegan (Robert Shaw), a high-stakes gambler during a poker game, they come up with a cunning method of manipulating him into placing sure bets on fixed horse races.
The incorporation of gambling, casinos, poker and other games in movies goes all the way back to the 1930's with "Gambling Lady" starring Barbara Stanwyck.
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