Classic Cartoons:
* Daffy Duck (Looney Tunes): While his manic energy often overshadows it, Daffy is deeply cynical and prone to self-pity, often lamenting his luck and complaining about the unfairness of the world.
* Snoopy (Peanuts): Snoopy's famous "World War I Flying Ace" fantasies are a coping mechanism for a world he often finds bleak, as shown in his many failures and his melancholic moments.
* Charlie Brown (Peanuts): The epitome of the "loser" archetype, Charlie Brown is eternally optimistic but perpetually unlucky, leading to a constant sense of disappointment.
* Droopy (Tex Avery): Droopy's laid-back demeanor often hides a cynical sense of apathy, as he often lets the situation play out in his favor with a deadpan expression.
* Porky Pig (Looney Tunes): Porky's stutters and panics are a reflection of his neurotic and anxious nature, often fearing the worst and expecting the worst to happen.
Modern Cartoons:
* Squidward Tentacles (Spongebob Squarepants): Squidward is a grumpy and misanthropic soul who is perpetually annoyed by his neighbors and his job. He sees the world as a chaotic mess he has to endure.
* R.I.P.D. (Rest in Peace Department) (R.I.P.D.): This animated film features a pair of afterlife cops, one of whom is a grizzled and pessimistic veteran who sees the afterlife as a bleak and depressing place.
* Eeyore (Winnie the Pooh): The embodiment of pessimism, Eeyore is a gloomy donkey who constantly complains and believes that everything is bad. Despite his negativity, he is actually quite caring and sensitive.
* Bender (Futurama): This cynical and sarcastic robot from the future is often seen as a nihilist, finding little meaning in life and constantly seeking hedonistic pleasures.
* Gumball Watterson (The Amazing World of Gumball): While often seen as a cheerful and energetic kid, Gumball's more serious moments reveal a tendency towards pessimism and self-doubt, especially when it comes to his own capabilities.
Bonus:
* The Grinch (How the Grinch Stole Christmas): While not strictly a cartoon, this beloved character is a prime example of a pessimistic and cynical soul who finds joy in spreading misery.
Remember, these are just a few examples. There are many other cartoon characters who could be considered pessimistic, depending on your interpretation. Pessimism, after all, is a matter of perspective!