Louis CK, Louie
Playing a fictionalized version of himself, Louie is a down-on-his-luck, stand-up comedian and divorced father of two. He’s got an inappropriate doctor, and it seems no one is really there to help him out. But he trucks along in New York, just trying to make it through the day.
Charlie Brown, The Charlie Brown and Snoopy Show
Influencing sad sacks for generations to come (paging George Michael Bluth!), the Peanuts character often found himself all alone in the pouring rain. Snoopy’s mischievous joie de vivre only made Charlie Brown’s hangdog demeanor that much more pronounced. And don’t get me started on that elusive football.
Debbie Downer, Saturday Night Live
”Always there to tell you about a new disease, a car accident or killer bees” — it’s right there in her theme song. Rachel Dratch may have cracked up while playing her, but it was a guffaw for help. Debbie isn’t happy unless you’re depressed. The quickest way for her to bring you down to her bummer level: Just mention feline AIDS.
Tobias Fünke, Arrested Development
A sad sack case could be made for most of the characters on Arrested Development, what with a failed magician (sorry, illusionist), an awkward (and possibly incestuous) teen, and a motherboy. But Tobias takes the banana stand. America’s favorite never nude was also a failed analyst/therapist… and a failed actor… a failed Blue Man… and just oblivious enough not to realize that mashing up his professions and calling himself an analrapist might not sit well with everyone.
Toby Flenderson, The Office
Rule-abiding and with a perpetual grimace on his face, Toby seems to hate fun. Or at least his penchant for shutting down all of the Dunder Mifflin crew’s best parties would suggest as much. He has an unrequited crush on Pam and even a trip to Costa Rica couldn’t make him exciting. To paraphrase Michael Scott, we hate so much about the things he chooses to be.
Toby Ziegler The West Wing
Another Toby in the mix? Sorry to say yes. President Bartlet’s communications director had his share of ups, including helping to save Social Security, but his downs — getting fired for leaking state secrets — were apocalyptic. Politics can be unpredictable, but Toby’s morose energy was consistent.
Moe, The Simpsons
Though Milhouse came a close second, Moe’s suicidal tendencies, desperate schemes, and inability to see a Bart Simpson prank call coming a mile away make him, for once in his life, the best at something. Unfortunately, it’s being the worst.
Lutz, 30 Rock
From pretending to own a car to making up a Canadian girlfriend, it’s no wonder no one wants to be around the TGS writer who is the real-life equivalent of Charlie Brown — if he’d grown up to be a pathetic man. Say it with me now: ”Shut up, Lutz!”
Jan Brady, The Brady Bunch
Middle child syndrome found a poster girl in Jan Brady. Her older sister was popular, and her younger sister had a cute lisp. Jan had a mouth full of metal, bordering-on-frizzy hair, and a raging case of insecurity. You know who had confidence to spare (despite a football to the face)? Marcia, Marcia, Marcia!
George Costanza, Seinfeld
Jerk store called…. Nothing ever really went right for the Lord of the Idiots. The only domain he ever mastered was Loserville. He does tend to find girlfriends, but something always goes horribly wrong. Self-loathing but content, he’s lucky he found three friends to hang around with exclusively.
Mr. Bates, Downton Abbey
To be fair, it’s not always his fault. But despite the fact that he found a little happiness with housemaid Anna, it was short-lived when he was convicted for his estranged wife’s murder. Sitting in prison (temporarily on death row) for a crime you didn’t commit? That’s not just sad. It’s tragic.
Jerry, Parks and Rec
The universe is full of contempt for him. He’s urinated in public (more than once!) and run off with a mural (or is it murinal?). He has a leg up on other sad sacks, though, because he is married with kids — for now.
Sacred Heart’s downtrodden lawyer couldn’t overcome the angst of his deep hatred for chief of medicine Dr. Bob Kelso. Add that on top of a way-too-close relationship with his mother, and you’ve got the makings of a perma-frown. If only his confidence-building a cappella group could always follow him around.
Skipper, Sex and the City
This perpetual nice guy always finished last when it came to on-again, off-again girlfriend Miranda. Constantly complaining that women didn’t appreciate his sensitivity, he finally landed a hot babe, only to dump her in flagrante when Miranda called. She was, of course, disgusted, and Skipper was alone again…naturally.
Cliff Clavin, Cheers
The postman who lives with his mother was so dumped-upon that his parade of pitiful went bicoastal, making its ways from Cheers in Boston to Frasier‘s Seattle. When your sadness needs two timeslots, it’s time to be concerned.
Dr. Zoidberg, Futurama
Hooray! People are paying attention to him — but for all the wrong reasons. His co-workers hate him, and he’s horrible at his profession. Bonus: He also smells, but what would you expect from an alien?
Eeyore, The New Adventures of Winnie the Pooh
Truly the saddest sack of all. The pretty ribbon on his tale might cheer him up — if he could ever find his tail, that is. Wah waaaaaaah.