"When I was young it seemed that life was so wonderful, A miracle, oh it was beautiful, magical. And all the birds in the trees, they'd be singing so happily Oh joyfully, oh, playfully watching me. But then they sent me away to teach me how to be sensible, Logical, oh responsible, practical. And then they showed me a world where I could be so dependable, Oh, clinical, oh, intellectual, cynical."
Jyu Viole Grace, aka 25th Baam, from Tower of God. Formerly a Wide-Eyed Idealist, a Na´ve Newcomer who couldn't even grasp why people would fight each other when they didn't do anything bad to each other before turned cynical survivalist that is content with making everybody drop-out of the test he participates in since it's fairer that way. He doesn't believe that there is a way for everybody to be happy and tries to create a certain kind of equality this way, all while trying to find the person who betrayed him.
One could consider Lelouch an example as well given his troubled backstory, only that the glasses he wears are of a much darker tint.
No matter how much the fandom hates him, Rossiu from Tengen Toppa Gurren Lagann got these around the time skip. He spent the first half of the series as an idealistic yet practical kid who truly believed in Kamina and Simon's quest for a new world. Then war happened to him, he spent years as the only intelligent person on a government council who deliberately slacked off so he'd do the paperwork for them, playing advisor to a guy who'd rather go for a stroll than actually govern his own damn country. The stress made him so jaded and cynical that he was willing to sacrifice Earth to save about 18% of humanity.
In Monster, when Johan isn't breaking cuties he's handing out jade coloured glasses. The protagonist of the series, Doctor Tenma, is his special project in this regard. Johan can never find a pair that fits Tenma, even when he attempts a Thanatos Gambit. What's more, at the conclusion, everyone who manages to survive ends up taking them off and starts rebuilding his or her life with optimistic outlook on life.
Back when he was a Self-Made Man in the court of his country, Sonken aka Chuutatsu from The Twelve Kingdoms witnessed a terrible level of corruption and cruelty. When chosen as the King of Hou, then, the Jade Colored Glasses were so firmly glued to King Chuutatsu's face to that he became an absolute Knight Templar and his absolute sense of justice caused him to slaughter a large portion of his own population for minor offenses. His zeal was so terrible that the minor noblemen rebelled, ovethrew and killed him, his kirin and his wife Queen Kekai, leaving his daughter Shoukei as the last survivor.
Also Queen Shushou of Kyou, who is a good person at heart but is also very much a Little Miss Snarker who keeps telling her kirin Kyouki that he's too good for his own benefit.
Sayaka comes to a point that she sports a pair after learning some grave facts about becoming a magical girl the hard way before becoming a witch.
Kyouko used to be a Wide-Eyed Idealist, but had her optimistic worldview shattered when her father killed her whole family and then himself after finding out people only listened to his preachings because of the wish she'd made.
Then it was invoked and then defied with this sentence: "If someone says it's wrong to hope, I will tell them that they're wrong every time. I could tell them that countless times."
Over the course of Neon Genesis Evangelion, Gendo Ikari shows shades of cynicism in all directions following the "death" of his wife, Yui Ikari, when Unit 01 sucks her soul inside it and turns her to LCL then failing miserably to resurrect her, and finally, discovering that the first Rei clone he ever made from his attempts to rescue Yui, the one remnant of his wife's image, had been mercilessly strangled by Naoko Akagi in a fit of distraught anger (hearing that Gendo called her useless from Rei's mouth made her think it was her old enemy Yui taunting her), who killed herself violently after seeing what she did. At some point in his life, Gendo became afraid of bonding with anyone, even his son, and, having lost the one person in his life who truly understood and loved him, turns intensely cold, impassive, and morally oblivious to whatever he tries to do- only Instrumentality matters, for it will let him see Yui once more. In the midst of all this, Gendo literally ends up wearing tinted glasses after his old ones break while rescuing Rei from a superheated Entry Plug. While Gendo might seem to be heartless, he's really a Jerk with a Heart of Gold- down deep, there is regret for what he's done.
Obito Uchiha in Naruto started out as a good kid until he got back from being crushed in a jutsu induced landslide just in time to see his best friend murder the girl he liked. After that, he starts an evil organization and plans to become a physical god.
Nagato could count as well. He started off as a sweet kid with hopes of changing the world for the better. But after being made into the universe's Chew Toy, and witnessing his best friend's death, he becomes determined that only pain can change the world.
In Chuunibyou Demo Koi sa Shitai!, Most cured chuunis wear some type of these, though they can differ. Some grow out of it on their own, while others have a pair beaten onto them by their family and friends.
Bleach: Flashbacks reveal that Ryuuken Ishida used to be a Wide-Eyed Idealist who was under a lot of pressure to protect the future of the Quincies. A series of disasters occurred that culminated in him suffering an Heroic BSOD. At some point between that event and the main storyline, his Heroic BSOD slid over the Despair Event Horizon and he's now very attached to the jade-coloured glasses he wears for all things Quincy. His son, who doesn't know the truth, is extremely frustrated with it.
In One Piece, we have the Seven Warlords of the Sea, barring Jinbe. The past of each member is heavily implied to be so sad that it practically left them jaded on their views of the sea.
Mimic of Marvel Comics' Exiles: An idealist superhero from a near-perfect universe, drafted into a dimension-hopping team, fixing "broken" realities. After seeing one too many far-from-perfect alternate versions of his colleagues, he snaps, and decides some people, and some worlds, aren't worth saving.
In Twisted Toyfare Theater, main character Spider-Man befell this fate by virtue of simply living in Megoville. Being the Only Sane Man in a world full of atomic supercrazies, several of whom routinely come over to his house uninvited, does that to a guy, to the point that he's completely unwilling to do anything even remotely heroic if he can avoid it.
Morpheus from The Matrix wears these while teaching Neo that the world he once thought to be real was just a computer simulation. If you add in the greenish tint of the Matrix scenes, it becomes literal as well as metaphorical.
Theo Faron in Children of Men was a daring Merry Prankster and activist before the world's population ceased growing. After the crisis, he is so jaded and tired that he can barely muster a tear for anything.
Happens to Harvey Dent in The Dark Knight after Rachel is killed, leading him to become Two-Face.
Michael Corleone from The Godfather started off as an idealist. He volunteered to fight in World War II and had no intention of becoming involved in the family business. Eventually, events suck him in but he thinks he can make the family give up the life and go into legitimate business. By the end of Part II Michael has become a cold cynical Mob boss.
The Picture of Dorian Gray's eponymous character was given jade-colored glasses by Lord Henry. Rather than being "broken," Lord Henry simply puts thoughts into Dorian's mind that reminds him of how terrible the world can be and the fleeting nature of youth, beauty and the sheer pleasure that can be derived from living a life of debauch and leaving notions of innocence and kindness behind.
Based on his backstory, Littlefinger went through the same cycle himself during his youth.
Brienne of Tarth manages to combine this with Wide-Eyed Idealist; she half-believes the world is like the songs, and is always shocked when someone breaks an oath or anything like that, but she's also resigned to never being able to sleep while there are strange men around, and occasionally having to beat seven shades of shit out of someone trying to rape her.
Although, to be honest, that didn't completely remove his naivete and beliefs about justice and honor, just diminished them. It was spending several years working in a corrupt, selfish, and paranoid government that resulted in glasses so jade he turned into a Villain Protagonist.
In Allegiance, Mara Jade, as the Emperor's Hand, tended to be sharp-tongued but was overall quite idealistic. She consciously felt that the Emperor was "a good and wise man", she believed that the Empire was fundamentally good with some foul elements that could be removed from within, and just in general she had a pretty stable existence. We see in Choices of One that she can't even really imagine being anything else, and finds the sensation of missing someone to be alien. The Emperor's death changed everything - his last command to her was "YOU WILL KILL LUKE SKYWALKER", and it echoed in her head at dangerous intervals, her Force-Sensitivity fluctuated on and off, and she saw the Empire for what it was - fundamentally foul with some good elements, and not ruled by anyone she felt was worthy. In the years after that she bounced between various non-Imperial non-Rebel groups, mostly smugglers, always leaving after her Force-Sensitivity flared up and made her employer uneasy, and although her last employer, Talon Karrde, was by far the best, by The Thrawn Trilogy she was highly cynical. Mara means "bitter", and "Jade" fits that (and one of creator Timothy Zahn's dictionaries also listed, as another meaning for Jade, "discarded woman").
Ben Skywalker puts on some very tinted glasses immediately after Mara's death. He's mostly an odd mix of idealistic and pragmatic (merging both of his parents' traits, leaning slightly towards the latter), but losing his mother, the one person in the galaxy that he loved and admired the most (and could talk to without fear of anything), clouded his judgment and even caused him to go so far as kill in the name of revenge, causing Luke to forcibly stop that last attempt at killing Jacen (who Ben correctly guessed as Mara's killer), at which point Ben realizes he's gone too far. He recovers from that phase fairly quickly, but the tint's never going to wear off.
"I saw my whole world, several million people, destroyed," she responded with chilling matter-of-factness. "Nothing mankind does surprises me anymore. [...] We have our devils and our angels, Luke. You have to be ready to handle both."
In Death: Eve Dallas definitely wears these. She claims that she can't remember being innocent, but New York To Dallas shows that the tint of those glasses obviously became darker since the time she was in uniform.
In The Dresden Files, a good example of this appears in "A Restoration of Faith," the short story that was the first appearance of Harry Dresden. Faith, a ten year old girl, has run away from her rich family home, where she states she isn't loved.
"I see these Disney shows about how much parents love their kids. How there's some sort of magical bond of love. But it's a lie. Like you and that troll." She laid her head against my shoulder, and I could feel the exhaustion in her body as she sagged against me. "There's no magic."
I fell silent for several paces as I carried her. It was hard to hear that from a kid. A ten-year-old girl's world should be full of music and giggling and notes and dolls and dreams—not harsh, barren, jaded reality. If there was no light in the heart of a child, a little girl like this, then what hope did any of us have?
Then Harry gets one for himself in the next paragraph.
A few paces later, I realized something I hadn't been admitting to myself. A quiet, cool little voice had been trying to tell me something I hadn't been willing to listen to. I was in the business of wizardry to try to help people; to try to make things better. But no matter how many evil spirits I confronted, no matter how many would-be black magicians I tracked down, there was always something else—something worse—waiting for me in the dark. No matter how many lost children I found, there would always be ten times as many who disappeared for good.
No matter how much I did, how much trash I cleaned up, it was only a drop in the ocean.
Discworld: When we first meet Sam Vimes, he's the ultimate cynic, and so beaten down by life that he has a serious drinking problem and doesn't even try to do his job. When we meet the 17-year-old Vimes in Night Watch, we discover he was idealistic and perky, and it took "30 years of being hammered on the anvil of life" to turn him into the man we know.
The Patrician, however (possibly the only character who's more cynical than Vimes) seems to have been born like that.
In Poul Anderson's Time Patrol story "Gibraltar Falls", Manse admits that Thomas succeeded correctly, and he had resisted not because it was wrong but because he had seen too often when it could not be done.
Arguably Will in Infernal Devices, as he alludes to a traumatic childhood quite often.
Subverted with Jem, who had a very traumatic experience and seems to function quite well outside his "illness".
The Thick of It: By the time we meet Hugh Abbot, he seems to have already not only earned his pair but glued them permanently to his face.
Yes Minister: Jim Hacker eventually gets these, but he has the heart (or lack of head) to take them off once in a while. Bernard follows a similar trajectory, while Sir Humphrey doesn't need them, as the lenses in his eyes were made of jade from birth.
Doctor Who has the Doctor himself. For all of his apparent youth and energy, it's hard to forget He's over a thousand years old and was forced to kill his own people in the Time War; he still retains a lot of idealism, but he lets the cynicism shine through every now and again. Very apparent with the eleventh and ninth doctors.
Marty and Thommo from Frontline. There are plenty of signs that they both used to care deeply about journalism, but had the idealism ground out of them by years of working in tabloid current affairs.
In Bunheads, Michelle started as a dancer with great potential that gradually let it fritter away until she wound up stuck in a dead end job as a Las Vegas showgirl.
Eliot: You have no idea who I was before all this started. That guy—kid—he had God in his heart and a flag on his shoulder. Clean hands. I haven't seen him in the mirror in more than ten years, and believe me—I get up every morning looking for him.
Charting Steely Dan's albums from Can't buy a Thrill to Gaucho will reveal a trajectory which slides further and further into cynicism. They were pretty damn cynical to begin with, but even the shaky optimism of "Change of the Guard" is long gone by the time of The Royal Scam.
Pink Floyd bought a pair after Syd Barrett left the group and reached its peak with The Wall and The Final Cut.
Pretty much the fate of the main protagonists from The Pretty Things' S.F. Sorrow and Frank Zappa's Joe's Garage. Both are idealistic, cheerful young men, but events in their lives (war and the death of his girlfriend with the former; abuse by the lackeys of the Cental Scrutinizer and banning of music with the latter) cause them to go insane. As a result, Sorrow see no one left to trust in life and shuts himself off from the world, while Joe is forced to conform to society as his hobbies are made illegal.
Finnish metal band Nightwish can be seen as this. While the earlier albums (from Angels Fall First to Wishmaster) high-fantasy and folk stories were a common occurrence in the lyrics and the music used to be more vivid and powerful, later albums (starting from Century Child) started bringing despair, loneliness and nostalgia for lost times as a common theme, and the introduction of a full orchestra for most of the songs brought an eerie "goth" feeling to the band, all of this culminating with Dark Passion Play, probably their darkest album overall.
When you were young and your heart was an open book You used to say live and let live (you know you did, you know you did, you know you did...) But if this ever-changing world in which we live in makes you give in and cry... Say Live and Let Die!
Both Sides Now by Joni Mitchell. Each verse presents the rose coloured glasses and then jade coloured glasses view of (clouds/love/life) but the chorus hints that maybe rose coloured is better.
BIONICLE: Brutaka lost any semblance of optimism after the Great Cataclysm, believing that Mata Nui had abandoned them. This led to him briefly undergoing a Face-Heel Turn during the Voya Nui / Mahri Nui arc. He stopped wearing the glasses when The Order of Mata Nui gave him a chance to redeem himself.
Nessiah (A.K.A. the grim angel Aries) from Yggdra Union was at first The Messiah. However, after getting cursed and thrown out of Asgard by the corrupt magi, he went insane and started the massive plan that destroyed countless people's lives in order to exact vengeance on Asgard. When The Messiah gets broken, the result is not pretty.
Lans Tartare (A.K.A. Alphonse in the gaiden Tactics Ogre: The Knight of Lodis) from Ogre Battle series starts out as a Wide-Eyed Idealist. However, after losing his best friend and lover by the end of the gaiden, he became a bitter cynic that we see in Tactics Ogre: Let Us Cling Together.
Auron in Final Fantasy X was a Wide-Eyed Idealist and true believer in his first pilgrimage with Braska, but after he found out the truth and was killed in Zanarkand, he became a much more sobering influence on the pilgrimage with Yuna.
In Baldur's Gate II, provided you don't give her a Happily Ever After ending as the Player Character's love interest, Aerie starts on the road towards getting one of these. In her ending, provided you didn't romance her or left her to ascend to godhood, she slips into the abyss during the course of a one-woman crusade towards slavery in the Sword Coast.
Aerie: I've... I've just been thinking. About all this death, all these horrifying thingsIrenicus has done. He actually stole a soul and... and all these people died for nothing... And for what? Some "vengeance" that Irenicus wants! For that he throws people aside like mere objects?! I... I cannot believe that such evil is allowed to exist! I will not sit idly by and be pathetic! I have paid too much attention to my own sorrows and experiences... and not enough to the evil that has surrounded me!
A possible fate for Commander Shepard in the Mass Effect series, depending on the player.
Garrus Vakarian's backstory has elements of this - idealistic young turian, wants to make a difference, joins C-Sec...and is promptly mummified with red tape.
Squall from Final Fantasy VIII pretty much had these welded onto his face from a young age, when his "sister" Ellone was taken away from his orphanage, and due to his use of Guardian Force junctions - which erased his memories - he never got over the trauma. As a result, Squall grew up believing that it was better to push everyone else away and refused to make friends or even have any ambitions beyond proving himself strong enough to take care of himself.
Alistair in Dragon Age: Origins loses his mentor, his place in the Grey Wardens and pretty much everything to his name during the course of his backstory and the first hour of the game. If you complete his personal quest in a way that shows to him that not even his own remaining family really cares about him unless it benefits them, he completes this transition.
In Katawa Shoujo, Akira Satou is, contrary to her appearance, somewhat cynical as a result of her parents having abandoned her and Lilly in Japan to pursue a business opportunity in Scotland. Late in Lilly's route, when their parents decide to have both of them come back to Scotland permanently, thus forcing Akira to break up with her boyfriend, and potentially doing the same to Lilly, despite Akira approving of her relationship with Hisao,, Akira says "life isn't a fairytale," and that some people will have no choice but to do things that hurt themselves or others in response to life's harsher events. In a subversion, if Hisao manages to play his cards right, Akira will regain her faith in love - she will go to Scotland, yes, but her boyfriend will go with her and Lilly will stay in Japan with Hisao.
John also gets hit by this in Act 6 as he grows up. In particular, he comes to realise that his beloved Con Air is actually a pretty terrible movie. Jade assures him that it's still a great Guilty Pleasure, but that doesn't help John, who sincerely used to believe it was good.
In Worm, the wise-cracking superhero Clockblocker, after dealing with the deaths or departure of most of his team and the fact that the supervillains enforcing brutal vigilante justice are better at keeping order than the sponsored superheroes starts seeing the world as this. Choice comments include that humanity is a "joke" and deserves what it gets.
Rev. Lovejoy of The Simpsons. Naturally, it was heavily implied that Flanders was solely responsible for beating the idealism out of him.
An Aqua Teen Hunger Force episode has a discount toy doll being drug addicted, alcoholic, nihilistic, and self-harming and convinces two characters to become depressingly nihilistic, with the second one (another, more expensive doll) driven to blowing his head off with a shotgun.
Played literally in the South Park episode "You're Getting Old" where Stan, upon reaching his 10th birthday, contracts 'cynicism' — depicted as a illness that causes everything you see to look like shit and everything you hear to sound like shit and everything you eat to taste like shit, etc. In the following episode he learns that the best way to treat his cynicism is by drinking alcohol.
One episode of Hey Arnold! had Eugene becoming this when he discovered his childhood hero was actually a Prima Donna actor. By the end of the episode, he gets better when said actor realizes he was wrong and decides to stand for the ideals of his character by saving the life of Eugene's younger friend.