Molokov and Walter are tag-team Chessmasters who play the protagonists against each other for political purposes in the musical Chess. Ironically, they are the only prominent characters who don't play chess in the show, and the ones they manipulate, are international chess grandmasters.
Prince Hal in Henry IV, Part 1 monologues about how he's using his time drinking, whoring and stealing with the lowest of ruffians as part of a public image long game. He's manipulating perceptions and expectations of him so that when he becomes the glorious, reformed king he knows he will be, it will appear that he has risen even higher by starting so very low. He plays everyone, from the Eastcheap rascals to his father the king. It's up to interpretation whether this makes him super cool or a total bastard.
Edmund, Regan, and Goneril from Shakespeare's King Lear. They all fully take advantage of their fathers' weaknesses.
Iago from Othello plays off of Barbantio's racism, Othello's jealousy and distrust in Desdemona, and Roderigo's love for Desdemona all to destroy a man he hates — but for whom he has no good reason to hate.
In the Oliver Parker film adaptation, Iago (played by Kenneth Branagh) illustrates his plan with an actual chessboard.
Interestingly enough, Iago is actually a failed Chessmaster — he allows his own personal hatred (and thus contempt) for Othello and women to screw up his plans — for instance, getting Emillia to steal the handkerchief but then thinking he can keep her quiet simply by ordering her to. An example of a chessmaster who really does win is Caesar from Antony and Cleopatra.
The Phantom of the Opera is initially the Chessmaster until the part where Christine rips his mask off and the theatre burns down. He even has a model of Il Muto where the characters have interchangeable heads to help him in his plans.
In Pokémon Live!, Giovanni orchestrates the entire plot and manipulates just about everyone.
In the musical Rudolf — Affaire Mayerling, the Classic Villain Graf Taaffe is playing chess throughout the story, sets The Hero Rudolf Checkmate during a song with Rudolf's lover Mary Vetsera and is actually revealed to be the one behind everything by having everyone including Rudolf's father Franz Joseph be his pawns.