Top 10 Television Sad Sacks

In the world of comedy, there are certain archetypes that every successful show typically has within its range of characters.  There’s the wisecracker, the square, the goofball, the square, the free spirit, the bully, the dork, among others, but maybe most entertaining of all is the sad sack.

A sad sack, by definition, is an inept and blundering person.  He walks into the room, and his mere presence makes everyone else want to get up and walk out.  But usually, he’s such a hapless dope you can’t help but find him lovable anyway, which is why we have to believe Charlie Brown might be the greatest sad sack of all time.  Here are ten of our favorite television sad sacks, complete with a Charlie Brown sad sack rating scale.

10.  George Michael Bluth (Arrested Development)

Overall, George Michael Bluth might not seem like much of a sad sack. After all, he’s mainly an overly nervous, naïve teenager with unnatural feelings for his cousin (who, by the way, fits the archetype of “the rebel”).  He doesn’t necessarily fit the role of a guy who forces others out of the room, but when you think about it, naiveté or not, there are few characters in recent memory who have bumbled their way through life more endearingly than George Michael.  Heck, they even devoted multiple scenes to the poor guy dragging his feet, walking sadly while the Charlie Brown music played.  When your writers are purposely comparing you to the greatest sad sack of all, we’re going to go ahead and lump you into the category.

Sad Sack Rating: 2 Charlie Browns out of 10

9.  Andy Millman (Extras)

Considering how few people ever saw this brilliant two-season series that Ricky Gervais brought to HBO, we realize most of you will likely have no idea who Andy Millman is.  Well, Andy Millman, as played by Gervais, is a struggling actor who wants desperately to find fame and fortune, but has to settle time and again for work as an extra.

Ultimately, he sells a television show to the BBC, but even that gets twisted and altered past recognition, and he’s forced to play a buffoon until, ultimately, he gives up the fame and fortune in the supposed name of integrity.  Naturally, things go from bad to worse, and this friendless, chubby man winds up having to settle for embarrassing guest-starring roles on Dr. Who and a spot in the Celebrity Big Brother house.  One look at Andy Millman’s face is all you need to see what a tremendous sad sack he really is.

Sad Sack Rating: 3 Charlie Browns out of 10

8.  Butters Stotch (South Park)

Butters Stotch is on the same sort of level as George Michael Bluth when it comes to sad sacks because, while he certainly is one, he’s blissfully unaware of that fact, and tries ever-so-hard to not be one.  Butters is the whipping boy of his group of “friends” who generally want nothing to do with him unless it involves his humiliation or their financial gain.  It’s actually kind of amazing how often those two things go hand-in-hand as well.  Heck, the poor kid can’t even use his one great talent, dancing, without setting off a chain reaction that results in tremendous bloodshed and chaos.

And speaking of chaos, when Butters finally snaps and takes on the persona of supervillain Professor Chaos, he can’t even get that right, being thwarted time and again by the fact that, well, The Simpsons already did everything he has planned.

Sad Sack Rating: 4 Charlie Browns out of 10

7.  Bill Haverchuck (Freaks and Geeks)

Out of all the freaks and all the geeks on the brilliant-but-cancelled series Freaks and Geeks, none was more of an outcast or a loser than Bill Haverchuck.  Well, perhaps loser is a bit strong, since poor Bill was a great kid who just had zero clue about how to fit in.  Among his very few friends, he was the one they held themselves up against to feel like maybe they aren’t so bad after all.  Bill is tall and gangly, and wears oversized glasses that fit awkwardly on his goofy face.  He’s a funny and loyal guy, but he’s also the guy in high school for whom you know nothing will ever come easy, if it ever comes at all.  In short, he’s the ultimate high school lovable loser.

Sad Sack Rating: 4.5 Charlie Browns out of 10

6.  George Costanza (Seinfeld)

Now if it weren’t for the fact that somehow, inexplicably, George Costanza was almost always dating someone and, by and large, they were way out of his league, we’d be apt to put him even higher on this list.  That’s particularly true when you realize that George is basically an imitation of the real life Larry David, himself a tremendous sad sack, as exhibited on Curb Your Enthusiasm.

Of course, while George typically has a woman in his life, he routinely botches both the relationships he wants, as well as his attempts to get out of those he doesn’t.  All of this, of course, culminates when he inadvertently kills his fiance with his penny-pinching ways, which in turn keeps him from inheriting her family’s vast fortune since, after all, he never legally became part of the family.

Sad Sack Rating: 5 Charlie Browns out of 10

5.  Murray Hewitt (Flight of the Conchords)

Poor, misguided Murray Hewitt works by day at the New Zealand consulate in New York and, by night, manages the struggling folk novelty duo Flight of the Conchords.  Dressed in shabby browns and yellows most days, and utterly clueless about how, well, pretty much anything works, Murray manages to maintain a positive spirit despite the fact that his band didn’t even realize he’d been separated from his wife and, when he quit his job at the consulate for greener pastures, no one even noticed during the six months that he was gone, allowing him to settle right back into his job without missing a beat.

Sad Sack Rating: 5.5 Charlie Browns out of 10

4.  Kirk Van Houten (The Simpsons)

There are so many characters from The Simpsons we could have included on this list it’s a little ridiculous, beginning with Hans Moleman or Gil Gunderson, for example.  Heck, Gil is based on Jack Lemmon’s character in Glengarry Glen Ross and, if you know anything about that movie, you know that’s not a compliment.

But we ultimately decided to go for Kirk Van Houten, the inept father of Milhouse and former cracker factory employee, who saw his wife leave him and wind up in the arms of one of the American Gladiators shortly thereafter.  He winds up living in a dingy apartment and sleeping in a racing car bed, and his misguided attempt to launch a singing career ends with his wallet and car stolen, along with an embarrassing and public rejection by his ex-wife.

Sad Sack Rating: 6.5 Charlie Browns out of 10

3.  Toby Flenderson (The Office)

Everything about Toby Flenderson, from his name, to his voice, to the overall lack of respect he commands around the office of Dunder-Mifflin, makes him one of our favorite sad sacks of all-time.  Toby is a divorced dad who pines for Pam, and who is absolutely loathed by Michael Scott for reasons that are known only to Michael Scott.  Heck, even when Michael has his diary read aloud at a hearing, and Toby makes an attempt to cheer him up, Michael responds by throwing Toby’s food on the floor.

Perhaps what best sums up just how much of a sad sack Toby is was when he left the office to head to Costa Rica and start a happier life, only to wind up in traction almost immediately upon arrival.  Nothing, and we mean nothing, can ever go right for Toby Flenderson.

Sad Sack Rating: 7.5 Charlie Browns out of 10

2.  Bill Dauterive (King of the Hill)

There have been few characters in movies or television who have been bigger sad sacks than Bill Dauterive, the former Army barber who hangs out with Hank Hill and the gang as they silently sip beer and chat about things like propane and the Dallas Cowboys.

Once upon a time Bill was a high school football star with long, flowing hair, but a wife who left him, and a long string of bad luck, has left him paunchy, bald and ultimately miserable.  He’s like an abused little puppy as he follows Hank around and, when he starts to influence how Hank’s son Bobby behaves after being dumped, Hank actually has to step in and stage an intervention for his kid.  When you’re being used as a cautionary tale, you know you’re just a top-notch sad sack.

Sad Sack Rating: 9 Charlie Browns out of 10

1.  Cliff Clavin (Cheers)

The ultimate television sad-sack, Cliff Clavin was a man who could do no right.  Here was a man who, when fortune finally smiled upon him on a fortuitous appearance on Jeopardy, bafflingly wagered everything in Final Jeopardy, despite his opponents being miles behind him, money-wise.  He, naturally, gave the completely wrong question, and lost all of his winnings in the process.

The bar know-it-all on the classic show Cheers, Cliff was a mailman, living at home with his mother in a bizarre arrangement that may or may not have involved them occasionally sharing a bed.  Even on shows in which he did not appear, he was still the butt of jokes, as when Woody Boyd shows up on the television show Frasier and informs the titular character that Cliff’s mail-order Bosnian bride chose to return to her war-torn home rather than stay with him.  Cliff Claven truly is the saddest sack of all.

Sad Sack Rating: 10 Charlie Browns out of 10

Written By Jeff Kelly

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