Recently I was out having a pint with some of my buddies, and as much as I enjoy their company, I kept thinking about which Cheers character with whom I would rather be at the bar. Like any neighborhood watering hole, Cheers was frequented by an array of different people and personalities, and since I spent a lot of time in my youth obsessing over the show, and the city of Boston, I thought “Why not rank the Cheers characters in the order I’d most like to sit down at a bar with”? So here we go.
This is a tough choice here. I absolutely adore Rebecca Howe and the beloved, late Kirstie Alley’s portrayal of her is fantastic. I know at the time fans were upset about the change in the show after Diane left, but I don’t think the show missed a beat by adding Rebecca. That said, I’m not sure I’d ever want to have a drink with her. In her finest moments, she was a strong, confident boss who navigated the pressures of having a corporate overlord watching the bar’s every choice, but in her lowest moments, she could be an emotional wreck. I’ve tipped back a few in my day with people like that and I’d be very nervous that after a couple of drinks, she’d break down. I’d rather be out with someone having a good time.
Dr. Fraiser Crane, brilliantly played by Kelsey Grammer was a staple on NBC for two decades, first on Cheers and then its spinoff, Fraiser (which is being revived on Paramount+). Grammer won all kinds of awards for playing the character on both shows, which he richly deserved. Let’s be honest here though, it might be a bit of a bore to hang out with Frasier for some drinks. His pompous nature would likely get very grating. On the positive side, whenever someone on the show had a problem, he was happy to provide free counseling, so maybe if times were tough, he’d be the perfect bar mate. On the other hand, sometimes the last thing I wanted was to get unsolicited advice from a guy at a bar, which was another of Frasier’s less endearing qualities.
Frasier’s wife on Cheers, Dr. Lilith Crane (Bebe Neuwirth), has a lot of the same qualities as Frasier. She’s sort of annoying, she’s a snob (maybe a bigger one than he is) and she’s uptight. She’s also incredibly witty and snarky, which are two qualities I love in a drinking buddy. It would be a lot easier to get past the snobbery after a couple of glasses of wine and Lilith started relaxing and letting her tight bun of hair down. I think she’d be very funny to hang out with once her guard qa down, and a little liquid courage would go a long way there. There’s just something about her wry wit underneath her icy, robotic outer shell that seems like it would be a lot of fun to experience. I can't wait to see how she shows up in the new Frasier series.
Ok, so what do you do with Woody? I don’t mean where do I put him on this list, I literally mean what do you do with him? Woody, played by Woody Harrelson in a role he wasn’t interested in at first, is easily the most lovable character on Cheers. He’s a country-bumpkin in the best sense of the term. He’s honest, he’s forthright, and he’s kind. He’s often accidentally funny, but who wants to drink with someone they are laughing at rather than with? Not me. I have nothing against Woody at all, so there are good reasons to avoid having a tipple with the man, but I worry I would spend a lot of my time bored and looking at my phone as Woody rambles on about how terrible French Lick, Indiana is compared to his hometown of Hanover, IN. While I’m here for trashing talking Larry Bird, that’s probably where my interests end, right?
7. Evan Drake
Over its 11 seasons, Cheers had a lot of guest stars, and for the most part, this list would get pretty out of control if I thought about all of them. However, one who I would love to have a drink with is Rebecca’s boss, Evan Drake. Mr. Drake, played by the always cool Tom Skerritt, is everything you want in a drinking buddy. He’s funny and he goes with the flow, no matter how nuts it gets. He navigates Rebecca’s overzealous crush on him well and seems to have a good time with all the shenanigans the Cheers regulars commit. He even hired Norm to paint his apartment. Plus, being as rich as he is, I’d count on him paying for the really good stuff on the top shelf.
Diane Chambers (Shelley Long) gets a bum rap from the other Cheers characters. As was too often common in that era, the smart person is the subject of ridicule rather than praise. She’d be fascinating to have a drink with. Who doesn’t want to sit around with someone and talk late into the night about all the great books of history, and Diane has a vast knowledge of them all. Plus, we have a lot in common. We’re both writers, we both attended Boston University and we both left Boston to start our careers, so we’d certainly have plenty of fodder to keep the conversation going!
Now we’re getting to the nitty gritty, the Cheers characters who really seem like they’d most fun to drink with. For pure hilarity and fun, you have to think Ernie "Coach" Pantusso, played by Nicholas Colasanto in a role that could’ve gone to Sid Caesar, if you can believe it, would be at the top. Sure, he’s kind of an idiot, like Woody, but Coach lived a whole more life than Woody ever did. He’s a former baseball coach, hence the nickname. He also served in the Navy during the Vietnam War. There would be all kinds of cool stories to share over a beer, assuming he remembers them all. Even if he forgot half of each story, he’d still be a blast to hang out with at the bar.
Cliff Claven, played by Pixar superstar John Ratzenberger, might not seem like a top choice here, but let me explain. Ask any of my friends, like the ones I was hanging with recently, and they’ll tell you I have the same knack for peppering in useless trivia into all my conversations. I say, “You know,” as often as Cliff does. I’ve long secretly dreamt of being on Jeopardy! and I love going to pub trivia nights at my local watering hole. Just imagine walking into your local dive for trivia with a former Jeopardy! almost champion who knows more useless facts than anyone you’ve ever met. We’d be unstoppable, which would mean free pitchers all night as the winners of every round!
Carla Tortelli (Rhea Perlman) on Cheers is everything I look for in a dive bar waitress. Most importantly, she’s snarky as hell. I have to admit, after a couple of beers, I can get pretty cynical and snarky, and I love someone who can match witty barbs thrown at other people. It’s not my best trait, but it’s one I share with Carla. I can totally see myself sitting on a patio in front of a bar on a busy street in Boston’s Back Bay throwing shade on everyone walking by with Carla. It would be one of those nights that I would laugh so hard it would hurt, especially because Carla wouldn’t even crack a smile as she wisecracked her way to last call.
This one gets a little weird because fans of the show will note that Sam Malone (Ted Danson) is a recovering alcoholic, so maybe having a drink isn’t the best idea. Well, I disagree. We might not end up getting whacky on the sauce together, but that wouldn’t stop me from having a great time hanging out with a former Red Sox pitcher with friends like Kevin McHale and Wade Boggs! I also really need to know exactly what happened with his sailboat that he bought with the money he got for selling Cheers when it ran aground between Seasons 5 and 6. I’ll still have a whisky, he’ll have club soda, or whatever.
Could there be anyone else at the top of the list of Cheers characters you’d want to have a drink with other than Norm Peterson? He's the every man, the salt of the earth, the guy that everyone is so happy to see when he darkens the door of Cheers that they all yell his name. Just like it says in the theme song, I want to go where everyone knows my name, just like Norm. George Wendt’s portrayal of Norm is just perfect. He’s happy-go-lucky when he needs to be and he’s the quippiest part of the gang of regulars. He’s loyal to his friends, especially Cliff, and he’s the one who everyone in the bar would choose to have a drink with, so who am I to disagree?
In my imaginary world where I don’t leave Boston after college, I think of myself walking down those stairs and feeling “home” with all the regulars at Cheers. The characters on Cheers feel, like so many of our favorite TV characters, like my buddies. It’s so good to know that even now, all these years later, those buddies are still everyone’s friends, and the show’s enduring appeal is due in large part to how great they are.