Characters You Feel Sorry For

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I find the sidekick/best friend characters are nearly always much more interesting than the main character, not only because they can get into trouble or do things that would for some reason make us uneasy if the main character did them, but also they usually take a lot more punishment. While Harry Potter was no stranger to pain and abuse, Ron always felt like he could never be as good as his brothers, he accidentally cast a spell on himself that made him burp up slugs, and whenever Harry was staying over Ron's mother was always much nicer to Harry. When their first school dance was coming up she bought something ugly for Ron to wear but picked out a nice green outfit for harry because it matched his eyes...

Tom from the Tom and Jerry cartoons. The vast majority of episodes has Tom pursuing Jerry for two major reasons:

It's his job as a domestic housecat. If he fails, he'll get kicked out of the house.

or

He's an alleycat and he needs to eat.

Which is why as a cat lover I've ALWAYS hated the Tom and Jerry cartoons. I've never seen one episode where things worked out for Tom (or at least without pain). Jerry rarely gets hurt in the cartoons compared to the degrees that Tom has. I enjoy the Itchy and Scratchy parody on The Simpsons more than I enjoy this.

Charles Muntz in Up. I dunno why they didn't just let him take the bird so he could get his credibility back. But the heros' refusal to do something that simple was what made him turn into even more of a villain.

Albus Dumbledore had the most tragic backstory out of all of the major characters. His family was destroyed because of Muggles . The only man he ever loved didn't really care about him and was only using him. And he spent most of his years fighting against an evil wizard without the government's approval. To make things all the more ironic, it wasn't an evil wizard that did him in. It was his own grief. By trying to see his family again, he recklessly sealed his faith and had to leave Harry Potter helpless in his darkest year.

Ahsoka Tano from that Star Wars: The Clone Wars cartoon. Especially at the last episodes where she felt like the Jedi Order didn't trust her anymore...

Xever (Fishface) from the Nick Teenage Mutant Ninja Turtles. He's a bad guy, but getting turned into a mutant fish with no legs just arms, being made to work with a guy who doesn't like you (Bradford) and not being able to breathe outside of water unless you have special equipment on must suck.

The AC from Brave Little Toaster.

On another note, I do feel bad for Harry Potter. He was stuck growing up with an abusive family and Dumbledore's excuse was "he was better off growing up away from the fame and magic". I call BS on that. I'm amazed that Harry was still able to have any capability to love considering his childhood. And very little was done to improve Harry's childhood considering how famous he was until the series started.

Of course I felt the worst for him in the fifth book and if you have read it, you would know why.

Ben "Ben X"
Edward "Edward Scissorhands"
Selma & Jeff "Dancer in the Dark"
Barry "Punch Drunk Love"
Brandon "Boys Don't Cry"
Setsuko and Seita "Grave of the Fireflies"
John Merrick "Elephant Man"
Chris McCandless "Into the Wild"
Jesus "Passion of the Christ"
Precious "Precious"
Wladyslaw Szpilman "The Pianist"
Jenny "Forrest Gump"
Ruth "Bastard out of Carolina"

When I was a kid I once watched a Filmation cartoon called Fraidy Cat. It was a about a poor, miserable, unlucky cat who used up 8 of all his 9 lives and just wants to make his final life last as long as possible, but every time he says a number from 1-9 or sometimes even a word that sounds like a number, a ghost from his past life would appear to haunt him and make him even more unhappy. And if that wasn't bad enough, if he said "9", a big thunder-cloud-monster in the shape of the number would appear and chase him around while firing lightening bolts. Ironically it had to be the worst one of all them all and he hadn't even lost his ninth life yet! It was supposed to be a funny cartoon, it was a bit creative with each of the ghosts being from a time in history like a cave-cat and his pet dinosaur from life 1, and a bumbling wizard cat, and a pirate-cat and such, but deep down I felt bad for him having to live in fear of even saying the numbers that would conjure them up. In one cartoon two other cats who are on their first lives tease Fraidy for being afraid of everything, especially numbers, but he explains they're not on their ninth live like he is, which of course makes the 9-monster appear and it even attacks the other two cats before going after Fraidy. So it's like, all cats in this show will eventually meet the same fate when 8 of their lives are used. Fridge logic horror, anyone?

Picard when he's assimilated by the Borg.
Jean Valjean in the novel and non-musical adaptations.
Titus Andronicus.
Julius Caesar (Rome HBO)
Hector.
HAL-even though he bloody deserved it.

#1 and I challenge anyone to beat this Maggie Fitzgerald from Million Dollar Baby, never cried during a movie before or since. I'm still a man though dammit! Her family are the lowest f*****g people that scene where they take her hand... I don't even want to talk about it. That movie is traumatizing no one should see it.

#2 Teddy Daniels from Shutter Island This movie actually made me cry too but not like Million Dollar Baby, by the end of Million Dollar Baby I had like snot all over face. That scene where he comes home and sees his wife tending to his children swimming in the back yard. Leonardo Dicaprio deserves an Oscar for that performance.

#3 Nina Tucker from Full Metal Alchemist, wow Shou Tucker is such a monster whoever that voice actor is, fantastic voice acting perfect for that role, that was traumatizing.

#4 Leonard from Memento - throw all those mementos away dude, just sit yourself in front of a TV with endless commercials. Don't let Teddy tell you about Sammy Jenkins, well you'll forget it anyway.

#5 Les from Special(Rx) This guy's life just gets worse and worse.

#6 The Elephant Man This movie nearly made me cry, probably should have, and probably will if I see it again.

#7 Like everyone from Requiem for a Dream, if hard drug consumption has gone down, it probably has a lot to do with this movie, also fairly traumatizing, Darren Aaronofsky

#8 Private Pyle from Full Metal Jacket WHAT IS YOUR MAJOR MALFUNCTION? IS THIS A JELLY DONUT PRIVATE PYLE? ARE YOU ALLOWED TO EAT JELLY DONUTS? No Sir.

Oh I can't believe I forgot about this one

Probably #4 or #5 Sam Bell From "Moon" Proving that figuring out who you are and what your purpose is can suck... a lot. whoever conceived this has a Fantastic imagination.

Honorable Mention Alex from A Clockwork Orange the eyecontraption and being reprogrammed not fun.

Anyone mention Meg Griffin of Family Guy, yet? She gets so much abuse from the people who are supposed to lover her, on top of bullying from the popular kids in school, that I can't help but feel sorry for her.
I also feel a great deal of sympathy for Moe Slezack (spelling?) from The Simpsons. The poor guy is suicidally depressed from feelings of being unloved. Part of it has to be his less than attractive physical appearance, plus his cynical, sometimes predatory personality when it comes to exploiting his bar customers' alcoholism, but what can I say - I feel for the guy.
I'd have mentioned Comic Book guy also of The Simpsons, as he had been a lonely nerd for most of the show. But as good fortune would have it, he recently found love with a Japanese hottie who is also a comic book nerd.

Eduard Scissorhands
Pinky from Pinky and the Brain
All the characters from A Requiem For A Dream
Lilja in Lilja 4-ever (swedish movie)

There are probably a lot more but I can't think of anymore right now

Chewbacca. For one, his planet is constantly being enslaved or attacked. Also, nearly every time he grunts, the rest of the group behaves as if he didn't say anything! Terrible.