You Didn’t Mess With Harry The Hat On ‘Cheers’

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On Monday we learned that Harry Anderson had passed away at the age of 65. And since, there have been a plethora of fitting tributes for the man that most people knew as Judge Harry Stone on Night Court. (Our own Alan Sepinwall has a great one right here.) But the first time a lot of us met Harry Anderson was during the first season of Cheers when he played a con man, named Harry the Hat, who was always swindling the regulars out of their money.

Harry the Hat wasn’t long for Cheers. He only appeared in three episodes over that first season. In the second, he was in one before Anderson’s new show, Night Court debuted as a mid-season replacement. Anderson would return twice more as Harry the Hat in the show’s sixth and 11th seasons, respectively. (As a kid, I found this all very confusing because on both Cheers and Night Court the character was both named “Harry,” so I just assumed he had to be the same character. That this same character would scam money from the happy hour crowd at Cheers in Boston, then, somehow, get back to New York to preside over a courtroom and hear some cases. Part of me still thinks this might be true.)

What I loved the most about Harry the Hat was that he truly loved the gang at Cheers. Sure, they were marks, but they were his marks. He’d take their money, but never enough to do any real damage. And if Harry the Hat saw that someone was there to do any real damage, well, Harry the Hat would use the full brunt of his powers to defend Cheers.

There are two instances that show off just how great Harry the Hat could be. The first involves Harry swindling Cliff Clavin out of free drinks and the second finds Harry the Hat — in the final season of Cheers — helping save Cheers from its rival, Gary’s Old Town Tavern.

True story: A few months ago I was at a local bar here in New York City and I was having a discussion with a friend of mine about Harry the Hat. (I am always up for Harry the Hat discussions.) We started talking about this upcoming scene and a gentleman next to us, who also loves this scene, overheard us and joined in the discussion. Then his friend asked what we were talking about so we actually performed this trick on this fourth party… and it worked! (Well, the first half at least.)

Harry the Hat strolls into Cheers and winds up betting Cliff a dime that he can drink Cliff’s shot, a shot that is now underneath Harry the Hat’s trademark fedora, without touching the hat. Cliff accepts the challenge. Harry goes under the bar and makes a few gulping noises, then tells Cliff that the challenge is completed. Cliff, not believing Harry the Hat, lifts up the fedora and then Harry drinks the shot, having never touched the hat.

This is great enough, but it gets better: Cliff, now angry, says he can do the same trick. So Cliff tries to recreate the joke, but while Cliff is under the bar making fake drinking noises, Harry drinks Cliff’s shot. When Harry lifts up the fedora, the drink is gone and pays Cliff a dime. For one dime, Harry the Hat winds up getting two shots. You see, he didn’t mind fooling the gang at Cheers and making them look silly, but there’s no real harm done here. Harry the Hat was a grifter with a heart of gold. This was first evidenced in “Pick a Con… Any Con” when Harry helps Coach out of a jam. Harry was so convincing that Sam thought Harry the Hat had double-crossed Coach, banning Harry from the bar before learning that Harry had actually secretly helped Coach. Anyway, there’s just something about scoundrels doing the right thing at the last minute that always gets me. It’s probably why I like characters like Harry the Hat and Han Solo so much. (Also, this is probably the first Harry the Hat and Han Solo comparison in history.)

Harry’s last appearance came in the final season of Cheers, in an episode titled “Bar Wars VII: The Naked Prey.” (Okay, maybe this episode title is really the first Cheers/Star Wars reference.) After Gary from Gary’s Old Town Tavern wins a St. Patrick’s Day bet with Sam Malone over which bar would make more money (Gary broke into Cheers and built a cement wall around the bar area so Cheers couldn’t sell any drinks), the gang from Cheers has to sing “Getting to Know You” up on Gary’s bar… naked. Sam vows revenge and goes to Harry the Hat for help. Harry refuses and tells Sam to just give up. When Sam goes over to Gary’s Old Town Tavern to offer a concession to the feud, a bulldozer shows up and demolishes Gary’s Old Town Tavern.

Later, Gary shows up at Cheers to gloat. At first, he blames Sam for destroying the bar in a prank that went too far, but then reveals that he had sold Gary’s Old Town Tavern to a real estate developer, who wanted to put in a shopping mall after the site was demolished, for a million dollars. Gary introduces the wealthy developer, who turns out to be… Harry the Hat. This is a particularly mean stunt with a lot of legal repercussions — one that cost Gary his bar — but by turning Sam down earlier, Harry ensured that no one at Cheers was involved in what happened. And in Harry’s mind it was justified because Gary had gone too far in humiliating probably the closest people Harry had to “friends.” This episode is basically “Harry the Hat Unleashed.” Because of Harry, Gary literally destroyed his own bar.

As Harry walks out of Cheers for the last time, he tells everyone, “I guess I’ve always had a soft spot for you lunkheads.” When Sam asks how they could repay him, Harry says, “You already have.” Of course, Harry the Hat had stolen all of the money out of the Cheers cash register, but considering that Cheers’ direct competition is now gone, this seems like a small price to pay.

Anyway, the lesson of all this was: Don’t mess with Harry the Hat or the people he considers friends. Also, we’ll miss you, Harry Anderson.

You can contact Mike Ryan directly on Twitter.