Harry Gittes, better known as Harry The Hat for his signature fedora, is a con artist and frequent jailbird. An occasional visitor to Cheers, Harry often attempts to swindle its customers and employees with various short cons. Sam has standing orders to have Harry thrown out of the bar on sight, but Harry will help out the gang at Cheers upon occasion—partly out of sentiment, and partly to protect the Cheers gang from operators even more unscrupulous than himself. As Harry notes, "I don't like the idea of someone else plucking my pigeons."

Harry appeared four times in the series’ first and second seasons, after which he disappeared until season six's "A Kiss is Still a Kiss". (Harry casually explained his long absence—when asked how long it had been since his last visit to Cheers, he replied it had been "two to ten, with time off for good behavior") After another long layoff, his final appearance was in the eleventh and final season ("Bar Wars VII: The Naked Prey"), during which he swindles Gary out of his bar as an act of revenge for making the central characters perform naked. In reality, Harry's long absences were due to Anderson's starring role on Night Court.

Harry the Hat was played by actor-magician Harry Anderson. The character's last name was only seen in the credits of one episode, and was never spoken aloud by any character.

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