If you follow the professional poker, it’s easy to pick favorites from the crowd of bold and brilliant players. But what about in fiction? Not all of these characters are tournament-worthy, but their stories contain some of our favorite fictional heists, advice, and of course, poker games.

Five: Rusty Ryan, Ocean’s 11. With high-sheen suits that he keeps clean the entire film despite constant snacking, Rusty not only plays poker, but also teaches its rules. To movie stars. Who are clearly total ingrates. He also keeps a straight face as he watches Danny Ocean sling poker metaphors left and right, which takes a moral constitution of steel—never mind the heist they’re pulling. And lest we forget, he happens to be clever enough to pull off that heist on three of Vegas’ biggest casinos. Badass, nacho munching, and tat-covered (check out the ink at his shirt cuffs), Rusty practically invented the smooth criminal.

Shining moment: “Who the hell is this?” “The man who’s robbing you.”

Four: The Gambler from the Kenny Rogers song The Gambler. Rusty Ryan may tolerate Danny Ocean’s sporadic poker metaphors, but the Gambler turns a whole litany of poker metaphors into a song. A song that rhymes. Talk about skills. The Gambler’s advice to the singer isn’t just true for poker, but for the big Hold‘em table of life:

• You got to know when to hold ‘em, know when to fold ‘em,
• Know when to walk away and know when to run.
• You never count your money when you’re sittin’ at the table.
• There’ll be time enough for countin’ when the dealin’s done.

The singer, having learned well, takes the Gambler’s advice to heart with a poker metaphor of his own: “In his final words I found an ace that I could keep.”

Shining moment: The Gambler dies at the end of the song, right? He just drops this life-changing advice, then “turns back towards the window, crushed out his cigarette and faded off to sleep.” This not one stanza after following his card-centric advice with “the best that you can hope for is to die in your sleep.”

So yeah, we guess he died, then. Talk about advice you won’t ever forget.

Three: Henry Gondorff, The Sting. If you haven’t seen The Sting, you’re missing out on some of the finest motion-picture-making of the 20th century. Rent it, RedBox it, call up whichever parent loves TCM most—whatever you do, see the film. Paul Newman plays poker genius and heist-guy Henry Gondorff opposite his partner-in-crime Robert Redford (as Jonny Hooker). Gondorff and Hooker manage to pull of a scam so elaborate that it not only covers poker playing, but also horse racing. It’s also a scam within a scam (within another scam). That takes total genius, and they pull it off amidst the crime-ridden ragtime backdrop of Depression-era Chicago.

Shining moment: When Gondorff and Hooker *SPOILER ALERT* amid cheers, laugher, and loot, revealing to the audience it was a *SPOILER ALERT* all along.

Two: James Bond, Casino Royale. Tuxedos. Martinis. Bond women. A twilit Montenegro and a swanky casino, plus a heist-in-progress. What’s not to love? Nothing, and that’s why James Bond got to the second spot on our list. It’s a plus that he plays in a super-high-stakes poker tournament (despite downing a poisoned drink), all while remaining the gentlemanly badass we know and love. Nobody wears a suit like Bond—and nobody fans a hand of cards like him, either.

Shining moment: This is a James Bond movie, right? Every moment is his shining moment.

One: Teddy “KGB,” Rounders. Matt Damon’s Rounders protagonist Mike McDermott definitely deserves some love, but he’s just not as crazy as KGB. KGB is a Russian mobster with a penchant for Hold’em who easily scoops up the talented McDermott’s $30,000 bankroll (meant to pay McDermott’s tuition). From the maddening way KGB gently picks apart his Oreo cookie (and who can’t relate to that?) to the utter lack of empathy he feels when he casually destroys Matt Damon’s life, KGB is nuts, and we love the unpredictability.

Shining moment: Watching him twist apart that first Oreo as we get a glimpse of the insanity staring into Matt Damon’s soul.

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