Casinos & Gambling Online

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. His best friend Jack Hayes (Jared Leto) is a self-employed pool cleaner.
Tobey Maguire at the WSOP's annual celebrity poker tournament in Las Vegas, July 2008.

According to Wikipedia: In 2004, Maguire took up tournament poker. He has finished in the money in several events and has been 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 has won $10 million by playing poker in Hollywood. Maguire played in the 2007 World Series of Poker.
Michael Cera playing poker at Fox Fall Season Launch Event, on 24th October 2005.
Emile Hirsch & Andrew Keegan attending the play "He Asked for It" premiere at Macha Theatre, West Hollywood, California.

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.
"Hard Eight" was originally called, "Sydney" and it was Paul Thomas Anderson’s first film.Matt Damon as Mike McDermott in "Rounders" (1998).

The movie is from a pre-Rounders generation and draws more on the old Vegas poker world.
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".

"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 the kid because--well, maybe just because he has it to share. The kid is named John (John C. Reilly).Movies like "Hard Eight" remind me of what original, compelling characters the movies can sometimes give us. Like David Mamet's "House of Games" or Mike Figgis' "Leaving Las Vegas", or the documentary "Crumb" they pay attention to the people who inhabit city nights according to their own rules, who have learned from experience and don't like to make the same mistake twice. At one point, when Clementine asks him a question, Sydney says, "You shouldn't ask a question like that unless you know the answer." Source: rogerebert.suntimes.com

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.
James Caan as Axel Freed in "The Gambler" (1974).

James Caan is Axel Freed, a professor in a New York City university that ironically also teaches Dostoyevsky’s The Gambler in his course. Not many films before or since have managed to capture the thrill of gambling, the constant risk taking and living on the edge, as this film managed to do so well.

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. Some of the more prominent films that revolve around the world of gambling:Sharon Stone as Ginger McKenna in "Casino" (1995).

Based on the book by Larry Shandling and Nicholas Pileggi, "Casino" was directed by Martin Scoresese, starring Robert De Niro as Sam "Ace" Rothstein, a character based on Frank Rosenthal, who ran casinos in Las Vegas in the 70’s, most notably the Stardust casino.Clive Owen as Jack Manfred in "Croupier" (1998).

Clive Owen stars as Jack Manfred, a croupier in a casino only to find out that his life would make a great novel. This neo film noir movie portrays a thrilling profile of life gambling and shows how real casinos operate.