In poker parlance, the term ’rounder’ usually refers to a person who plays poker for a living and, quite literally, ‘does the rounds’, travelling from place to place in search of gambling opportunities. Directed by John Dahl and starring Matt Damon and Edward Norton, ‘Rounders’ is a 1998 drama, which chronicles the attempt by two friends to clear a series of gambling debts.

Mike McDermott (Damon) is a gifted, and honest, poker player, while his childhood friend Lester ‘Worm’ Murphy (Norton) is a self-confessed cheat, who is serving time for distributing counterfeit credit cards at the start of the film. Having lost his entire $30,000 bankroll to Russian mafioso Teddy ‘KGB’ in a single hand, McDermott shies away from poker and focuses on his law studies, working part-time to get by financially.

However, Murphy is released from prison with a previous debt of $25,000 still outstanding, so McDermott begrudgingly sets him up with games and allows him to play on his credit at the Chesterfield Club. Murphy takes out $10,000 and begins a tab in McDermott’s name, before the debt is sold to Grama, a brutish hood employed by KGB. Grama takes the $10,000 and, later, gives them five days to raise the additional $15,000.

Having tried, and failed, to do so, McDermott turns in desperation to his law school professor, Abe Petrovsky (Martin Landau) for a loan of $10,000. McDermott once again faces KGB, heads-up, for the outstanding debt. Having won $20,000, McDermott is taunted into continuing playing, but eventually wins over $60,000, which is enough to pay off all their debts and restore his original bankroll.

It would be fair to say that Rounders divided critical opinion. Stephen Hunter of the Washington Post wrote, ‘It’s a movie of character and milieu, both of which it evokes brilliantly’, while Trevor Johnston of Time Out was less complimentary, writing, ‘The end result is still short of a winning hand, since the screenplay is so utterly predictable.’

Owning Mahowny

Loosely based on the non-fiction bestseller ‘Stung: The Incredible Obsession of Brian Molony’, written by Gary Ross and published in 1987, Owning Mahowny is a 2003 drama directed by Richard Kwietniowski. The late Philip Seymour Hoffman stars as the eponymous Dan Mahowny, a soft-spoken, generally unremarkable banker who, nonetheless, suffers from an insatiable gambling habit. Deeply indebted to, and temporarily cut off by, his bookmaker Frank Perlin (Maury Chaykin), Mahowny resolves to embezzle sufficient funds from his employer, the Canadian Imperial Bank of Commerce, to clear his debts.

However, Mahowny soon progresses to stealing larger sums and flying to Atlantic City, where unscrupulous casino manager Victor Foss (John Hurt) is only too happy to facilitate his habit. Mahowny, though, has no interest in the perks typically offered to high rollers. Luxury suites, fine dining and top-shelf drinks, not to mention prostitutes, merely serve as distractions from the task in hand. He gambles recklessly, giving little or no thought to winning or losing, but driven solely by the overriding compulsion to get his money – as much as possible – on the table.

Unsurprisingly, Mahowny continues his downward spiral, ultimately committing the largest one-man bank fraud in Canadian history by defrauding his employer of a total of $10.2 million over a two-year period. Inevitably, his wrongdoing is discovered and Mahowny is arrested, prosecuted and imprisoned. However, viewers can take a crumb of comfort from the epilogue, which explains that Mahowny, or Molony, subsequently gave up gambling and married his long-suffering fiancee Belinda (Minnie Driver).

Ann Hornaday of the Washington Post wrote of Owning Mahowny, ‘The filmmakers have taken a bet that an unsexy, unpretty and unconventional movie about bank robbery and gambling can be as captivating as its flashier mainstream counterparts, and they’ve won.’

The Gambler

Released in 2014, The Gambler is crime drama written by William Monahan and directed by Rupert Wyatt. It is actually a remake of the film of the same name, written by James Toback, directed by Karel Reisz and released in 1974. The original drew its inspiration from a novella of the same name by celebrated Russian novelist Fyodor Dostoevsky, which was first published in 1866.

Jim Bennett (Mark Wahlberg) is a talented, no-nonsense literature professor at an unnamed Los Angeles college. However, despite his privileged background, Bennett is consumed by self-loathing and self-destructive tendencies, which manifest themselves as desire to fritter away bundles on blackjack and roulette. At the end of the film, Bennett says, ‘I am not a gambler’ and he is not, at least not in the traditional sense of the word.

Bennett does take significant risks, such as offering his own life as collateral for $50,000 he borrows from ruthless loan shark Neville Baraka ( Michael Kenneth Williams) in a vain attempt to recoup the $200,000 he already owes to Korean crime lord Mr. Lee (Alvin Ing). Insightfully, Baraka tells Bennett, ‘I think you’re the kind of guy who likes to lose’, and his gambling habits – continually doubling up bets, chasing his losses and so on – do little to suggest otherwise.

Increasingly desperate, turns to another loan shark, ‘Little’ Frank Brie, and then to his wealthy mother, Roberta, for the money to pay off his debts. Roberta agrees, but Bennett takes the money to a casino and loses it all. Bennett finally manages to pay off Baraka with his winnings from a ‘fixed’ college basketball game and in a last, desperate spin of the roulette wheel, wins enough to pay off his remaining debts.