In episode 22 of Keroro Gunsou, a missive from headquarters results in Private Tamama (temporarily) becoming the new leader of the squad. He promptly goes mad with power, and ends up throwing the Hinatas, Moa, and all his squadmates in the brig. While the others manage to make themselves comfortable (thanks to a few secret modifications Kururu made), Tamama ends up bitter and alone.
The Emperor in Photon has been the sole and absolute ruler of the galaxy for a few thousand years, and it became so boring that he allowed one of his subordinates to hatch a plan to achieve ultimate power and depose him, just so he'd have someone powerful to fight at the end.
Coyote Starrk from the Espada in Bleach. All of the ten Espada represent an aspect of death; his is 'Loneliness' because his enormous powers tended to drain the life out of any other Hollows who came near him and resulted in all of them avoiding him like the plague. He eventually split his soul into two seperate beings just to have someone he could hang out with: the other part became his Fracción, LilynetteGingerback.
In Chapter 422, Ichigo claims that Aizen was Lonely at the Top all along. When he and Aizen fought, the only thing he could sense from Aizen's zanpakatou was "solitude". He believes that the Hogyouku, rather than rejecting Aizen as a master, had finally granted Aizen's true wish: to be a "normal" Shinigami. Why it felt the way to do this was to give him more and more power until the very last second when it takes that power back is anyone's guess. The claim also tends to lose some impact given his previous and subsequent arrogance, and the fact that all of his actions were in the interest of becoming god.
Both Unohana and Kenpachi were revealed to be this before they first met. They were both killing criminals, desperately trying to find a Worthy Opponent. When they found each other, they both felt the rush and fear of battle. In fact, this was what caused Kenpachi to become a Blood Knight. However, even as a child he was stronger than Unohana, and his fear at being unable to experience that rush again caused him to subconsciously limit his power, along consciously limiting it with his eyepatch. Causing him to do this is what Unohana, even to this day, considers her greatest sin and regret.
Subverted in Death Note, where Light is shown to betray anyone and everyone in order to get to the top and become the god of the new world. One would expect that in the end, everyone is shown realizing this and turning against him - however, it is shown that even years after his death, there are still many worshipers who greatly mourn his death. (But that doesn't do him much good now does it?)
It's implied that successfully killing L has left Light bored and depressed, because good ol' L was the only person as smart as Light (and thus one of the few people he could relate to on any level). The sheer joy he expresses when he thinks he's found a replacement for L, and the rage he expresses when the new L doesn't live up to his expectations add to this interpretation.
Almost happens in Code Geass, when Lelouch loses his sister, his friends, and the Black Knights, but then subverted when he rekindles his friendship with Suzaku and C.C. regains her memories.
Hotohori from Fushigi Yuugi. And he felt like a bird in a golden cage.
He still has Hilda at his side, of course, having even worse social skills than Yang, the clod does not see it
Arguably subverted. He eventually gets a clue and marries Hilda. It's even theorized in-universe that his early death less than a year after taking over the known universe was either because of this trope hitting him fatally hard, or to avoid it (there being nothing else to conquer).
A One Piece omake did this when it imagined the Straw Hats as mobsters. They each end up killing each other (except for Nami, who dies of happiness after seeing so much gold) until the only one left is Luffy, who at first is ecstatic over having all the meat to himself...until he realizes how lonely he is without anyone to share it with.
This may be the case with World's Strongest Swordsman Mihawk. His expression is always stern and he rarely ever acts unless its out of some form of curiosity. Being the best swordsman in the world has obviously left him with not much to do while waiting for a half decent challenger.
This trope summerises the plot line of Ex Machina rather succinctly at least the abondonment of everything in pursuit of the dream although he never does make it to the top.
In the comic Timespirits, a space pirate has the Curse of Success - she succeeds at everything she tries, gets everything she wants. And she gladly gets the curse removed because, as she puts it, "I am so incredibly bored!"
Ozymandias in Watchmen, hidden under dense layers of ego and posing for the eyes of history. The reveal is his insecure last exchange with Dr Manhattan.
The title character in Cerebus. He is told to his face, by someone in a position to know (albeit someone later revealed to also be far from objective), that he will "die alone, unmourned and unloved" about a third of the way through.
Marvel's Thanos attempts to impress Lady Death by collecting the six Infinity Gems, and with them becoming her equal so she will finally speak to him. However, after he succeeds she still remains silent, one of her servants explaining that by becoming all-powerful he is now her superior.
Legion Of Super-Heroes: Brainiac 5 is the most intelligent person in history. His childhood was spent in the care of robots because his society rejected him as an aberration, and many of his teammates are hostile because he isn't sociable or nice. Cause you learn to be sociable and nice when you have no contact with living beings and are punished for displays of emotion for the first twelve years of your life.
In the Lunaverse story Carrot Top Season, Carrot Top diagnoses the Apple Trust as suffering from this.
“None of the Trust teams had any friends of supporters come with – didn’t you notice? I don’t think Applejack’s the only Trust farmer who’s completely isolated on her farm. I’d rather have my friends than a pile of bits and nopony to care about me.”
Michael Corleone in The Godfather, with the added twist that, initially at least, he didn't even want to be the head of the 'family business'
Iron Man: Initially, Tony Stark. He is the richest, smartest, most handsome, and most popular man in the world, who can essentially order beautiful women for...dinner. However, he has absolutely no family to speak of, and even Pepper doesn't really count as a friend so much as an insanely loyal employee, and when he admits this to Yinsen, he sadly remarks that Stark is "a man who has everything and nothing."
The Bio PicThe Life and Death of Peter Sellers posits that Sellers' life came down to this; by the end he's sadly watching home movies of him with his family and friends — all either dead or distant — and mourning all he's lost, and the only art he accomplishes in his final years that means anything to him is getting the film adaptation of Being There made. (Sellers was in fact an intensely nostalgic man, but he wasn't that lonely at the end of it all.)
One of the points of the Stop Motion short film MORE. And it is even more depressing than the Touhou example below.
George Simmons in Funny People is a famous and successful comedian internationally recognized through his movies, but he comes to realize that he's gradually pushed away everyone who ever cared about him, his movies are Lowest Common Denominator rubbish, and he's doomed to die a lonely and empty failure if he doesn't change his ways. Played with, however, in that it's not just achieving fame that is responsible for him being this way, but deep-seated emotional problems and self-loathing which stems back to way before he became successful.
Played with in that it's implied that their emotional problems are part of what makes the characters good comedians, at least initially. Meaning that to get the top you have to be somehow lonely in the first place.
This is the point of the classic British film Room At The Top.
Nicolas Cage's character in The Family Man, although he doesn't realize it until he's shown what might have been had he not embarked on his high-powered Wall Street career.
Daniel Day Lewis's character at the end of There Will Be Blood. But he outright says that he prefers it that way.
There are times when I look at people and I see nothing worth liking. I want to earn enough money that I can get away from everyone.
Tracy Flick in Election. Dave even tells her when the two are dating.
Eddie’s ex wife also dumped him while she was under the NZT’s influence. Eddie would have not contacted her if not for his own problems with NZT.
In the epilogue of Conan the Barbarian and Conan The Destroyer, Conan is seen sitting on the throne he had been promised in the first movie. However, his dark expression and pensive pose show that it has brought him no comfort.
A literal example of this happens in Wreck It Ralph where Ralph gets the medal he wanted, returns to his game, and gets the key to the penthouse which he was told he would never get but had to destroy Vanellope's racecar to prevent her from racing (breaking the little girl's heart in the process) and Fix-It Felix has left the game trying to find him and didn't return causing the other Nicelanders to panic and abandon the game which is about to be unplugged
Ralph: "I don't know, I just... I was just tired of living alone in the garbage."
Gene: "Well, now you can live alone in the penthouse."
The Dark Tower: Roland reaches the Dark Tower and climbs to the top, saving everything in existence from extinction along the way—but Roland himself is condemned to repeat his life over and over for the cruelties he committed in the name of this goal. It's implied that he only has to do it till he gets it right.
Dragaera: In the "bored with power" variant, sorceress Sethra Lavode in Steven Brust's novels creates an alternate persona, Kiera the Thief, who doesn't use her powers initially as a means of getting information, then continues the act because of the excitement of actually facing challenging situations again.
Paul Atreides in Dune Messiah. Even moreso his son Leto II. His grand design relied on purposely alienating himself from humanity, and turning into an ageless giant worm was a good start. After his sister who he shared an empathic bond with died, there was no one left to understand him. The ones who came close could only pity him.
In the Heralds of Valdemar series Vanyel suffers particularly from this. Between being a ridiculously powerful Herald-Mage, his sexual preferences and his fear of letting anyone close in case they become a target, he has experienced this increasingly over the years.
Vanyel: “Heralds are all lonely; we’re different ... Herald-Mages are one step lonelier than that. Then there’s me.” Magic’s Promise
In Atlas Shrugged the gifted scientist Dr. Robert Stadler states explicitly that is very lonely on the highest branches of the tree of intellect and is delighted to find “a work of genius that I didn’t create” (Galt’s motor). Life is pretty lonely for the Fiction500 characters, though it’s implied that only the “intellectuals”, leftist politicians, businessman who can’t operate in a free market and other powerful but talentless people envy them and wish to destroy them, whereas members of the public are not driven by envy and are given hope in an apparently hopeless situation by seeing great accomplishments from productive people.
The Fountainhead: Gail Wynand's entire life. Ayn Rand set out to do this quite deliberately. Her notes describe him as "a man who could have been", and he himself echoes that sentiment at the end.
One of William Gibson's short stories concerns a player of air combat simulations who's getting old but retains both his skill and a natural charm that allows him to befriend everyone at the local bar. A younger player meets a girl who Does Not Like Men and has a stash of upper-type drugs, and he threatens to rape her so as to intimidate her into handing over said drugs, which he figures will temporarily improve his skill so he can beat the older player. He does—but everyone's certain he cheated, and the older player continues to be the toast of the town while the younger one becomes a social outcast.
It's worse than that: the older player is a parapalegic war veteran, and being the dogfight simulation champion seems to be one of the few genuine joys he has in life, making the new guy's win seem almost as pointlessly cruel as his attack on the girl to get the drugs.
Older Than Feudalism: One king of Israel in The Bible, most likely Solomon, lamented in the book of Ecclesiastes over all the vanity in his life.
A Christmas Carol: Ebeneezer Scrooge. He is easily the wealthiest man in London, but is bitter, uncaring, estranged from what family he has left (his sister's son). He is disliked by the rest of town, having lost his sister, fiance', and best friend along the road to riches.
Edwin Arlington Robinson's poem "Richard Cory", and the song of the same title by Simon & Garfunkel.
Dragonlance: Legends: Of all the Very Bad Things in the trilogy, perhaps the most horrifying is Astinus's description of how absolutely lonely Raistlin will be when he finally achieves his evil ambitions.
The title character in Jack London's semi-autobiographical novel Martin Eden.
Harry Potter: Voldemort. He has no family having murdered his own father and his grandparents. Most people are downright terrified of him, including a lot of his followers. Even though Bellatrix is loyal and attracted to him, he can never love.
Judge Dee: When it becomes obvious that Dee is on the fast-track to promotion to Lord Chief Justice of all China, he begins to remember what his father, himself as prominent official, told him in his youth: "It's very lonely, at the top."
C. S. Lewis's The Magician's Nephew: Jadis sums the trope up pretty well, but she actually means it as a sort of self-praise: Jadis: "Ours is a high and lonely destiny."
Diggory notes that his uncle said the same thing, but it sounds a lot better when Jadis says it because she's a seven-foot-tall, dazzlingly beautiful sorceress (who, not coincidentally, nuked her entire world so she could be its sole queen.)
In Freedom, Loki/Gragg realises this of himself. He's the highest-level Darknet operative, but nobody thinks well of him.
In Warrior Cats, Mapleshade knows that Crookedstar will become clan leader, so she aims to get his entire family killed and make his this. Her plan fails when Crookedstar explains that once his time is over, everyone he cares about will be waiting for him in the afterlife.
Sister Carrie: The title character achieves her dream of Broadway stardom. This is after she has lost her innocence, become estranged from her family, worked her way through a string of lovers, and watched her self-destructive ex-husband blow through his fortune, wind up homeless, and ultimately commit suicide. Therefore, with the knowledge of all she has lost and the disillusionment it has caused, living her dream can never make her happy. The final lines of the novel sum up her situation perfectly:
In your rocking-chair, by your window dreaming, shall you long, alone. In your rocking-chair, by your window, shall you dream such happiness as you may never feel.
Although not really covered in the film, Matt Stover's novelization of Star Wars: Episode III - Revenge of the Sith notes this regarding Anakin Skywalker's transformation to Darth Vader, calling it the trap of the Sith. In becoming Vader, he has lost everything he cares about and he wants to lash out at the Emperor after he tells him the truth of Padme's death, but he lacks even the power to do that. And he finds that he doesn't even really wants to, for the Emperor is all he has.
Star Command: Shane Ridnaur explains this to a cadet. The commanding officer is alone and must appear invincible to encourage confidence among the crew. Also titled “In the Fold”. (This is a tv movie and not a film, therefore it belongs in the live action tv folder.) 
Many, many episodes of The Twilight Zone. "The Mirror" is a famous example. Also "Of Late I Think Of Cliffordville", where this trope is one of the protagonist's motives for accepting the Deal with the Devil.
Star Trek: The Next Generation, "True Q," uses the "boredom of power" version. This trope can also apply to the Borg Queen and her chasing after Picard. Yes, his main purpose was to facilitate the assimilation of Humanity, but judging by First Contact, A certain evil queen was getting lonely.
Chaotics: Oh, Arachnia, my love, my life! How well you understand our plight. If it weren't beneath my dignity, I... I would weep! How I've longed for someone who would understand! Arachnia: We have a saying on Arachnia. It's lonely at the top.
Most Anvilicious example ever: the first season of Degrassi Junior High. Stephanie becomes the most popular girl in school by lying and exploiting her friends — until the season finale, when her victims finally turn the tables on her. Cue flashbacks of every despicable thing she did. Then we see Stephanie crying in the bathroom, and she moans, "I only wanted them to like me!"
A season of Angel ends with Cordelia rising to a higher plane of existence and becoming, essentially, a goddess. The next season's opening episode shows her in all her god-like glory whining, "God, I'm so bored!" For a good chunk of the next season, she watches her earthly friends assume she's in a better place while trying helplessly to get them to bring her back.
In the Doctor Who story Invasion of Time, it looks like the Doctor has done this, abandoning his companion to become Lord President of Gallifrey, and then aiding an alien invasion of his home planet. It all turns out to be a heroic plan.
Kazran Sardick in A Christmas Carol which, obviously, draws inspiration from the Charles Dickens story.
Sidney Teal, the eponymous billionaire mugger in the Monk episode "Mr. Monk and the Billionaire Mugger", His chauffeur says that despite having a huge house, incredible riches, and a beautiful wife, Teal was the loneliest guy in the world. Eventually it's revealed that the reason he was performed the mugging that got him shot dead was that he was trying to relive the one moment in his life when he truly felt cool; in college, his friend pretended to mug him and then be scared off so that Teal could impress a date. The same friend went on to have an affair with Teal's wife and to get him out of the way, asked him to stage a fake mugging to impress a girl as an excuse to shoot him.
During an episode of NUMB3RS, Charlie and Larry went to a funeral of one of Larry's colleagues. Larry laments how the man was brilliant and a genius and yet, there was no one else at the funeral except for the two of them.
ER: The funeral of Doctor Romano, is attended solely by Dr Corday. Romano was a Jerk Ass to many of his colleagues and patients.
This is the theme of Stars and the Moon, signature song of Jason Robert Brown.
The basic idea of Kanye West's "808s and Heartbreak" album, especially the track "Welcome to Heartbreak." "My friend showed me pictures of his kids / and all I could show him was pictures of my cribs / he said his daughter got a brand new report card / and all I got was a brand new sports car"
Kanye's newest album, My Beautiful Dark Twisted Fantasy, has this in spades.
A theme in many of Eminem's songs but particularly, 'Say Goodbye Hollywood,' which contains the lyrics: "I sold my soul to the devil, I'll never get it back, if I could go back I never woulda rapped" and "'Cause all I wanted was to give Hailie the life I never had, instead I forced us to live alienated.'
The very first sentence of Gang Starr's Moment of Truth. "They say it's lonely at the top in whatever you do."
To The End by My Chemical Romance. The first verse is (if you're reading the lyrics literally) about a guy who lives alone in a giant mansion and kills people. Including everyone who attends his wedding. And later, his wife. Then again, if you're killing everyone in your neighborhood...
Doomsday Clock by Smashing Pumpkins.
Randy Newman - Lonely at the Top
The narrator of Jamey Johnson's Lonely at the Top (co-written by the late Keith Whitley) is a rising Country Music star who begins to complain about the pressure and fame brought upon by his newfound success. A fellow bar patron offers this wry remark: "it might be Lonely at the Top, but it's a bitch at the bottom."
Macbeth: Macbeth realizes that all the power he has gained is meaningless for the evil he has had to do to attain it. His former comrades are revolting against him, his wife is dead, and the events that foretell his death are coming to pass; he concludes that Life "is a tale told by an idiot, full of sound and fury, signifying nothing." On the very day of his coronation, he laments that by fulfilling the witches' prophecy, he's also ensured that Banquo's descendants, not his, would be the future kings of Scotland. "I'm the one who orchestrated Duncan's murder, and he gets to have the dynasty! Stupid worthless crown!" Even worse, he knew this would happen because the witches told him. Needless to say, it was all downhill from there.
An Irish play called The Field ends with an old man getting exactly what he wants, the titular field. However, he gets it at the expense of both of his sons, his wife, and any and all respect he had from local townspeople. And, because he wanted the land for the purpose of leaving a legacy to his family, when he does get the field, it's worthless.
In Wicked, this is the main thrust of the song "Thank Goodness''. Glinda finds that even though she is heralded as a hero throughout the kingdom and fiancee to a man she loves, she feels dissatisfied.
Glinda: I couldn't be happier! That's right, I couldn't be happier! Though it is, I admit, the tiniest bit, unlike I anticipated But I couldn't be happier! Yes, I couldn't be happier! Well, not simply. Strange though it seems, getting your dreams, is a little bit complicated There's a kind of a sort of...cost There's a couple things that got...lost There are bridges you crossed you didn't know you crossed until you crossed them!
Endemic to Ravenloft, the Dungeons & Dragons setting of Gothic Horror; since the Dark Powers seem to enjoy giving bad people new and interesting ways to live an eternity of suck, this is not particularly surprising. To give some examples from its ample supply of Darklords:
Count Strahd: murdered his brother in order to ensure his own immortality, thereby making his brother's betrothed - who Strahd was in love with - hurl herself over the walls of Strahd's castle.
Azalin Rex: killed his only son for being "unworthy" (read: still possessing a conscience), and would dearly love to bring him back but his curse means he can't learn new magic, which would be required.
Jacqueline Renier, who is perhaps the queen of this trope. Intensely monophobic, she has to spend her time with her vicious family, all of whom hate her, and will transform into a wererat in the company of anyone she actually cares for.
In summary: it really really sucks to be a Darklord.
The God-Emperor of Warhammer 40k. Let's face it. His obesession being the survival of mankind, he has really lost everything, his sons, the atheism he tried to build up in his Imperium, his self-respect, many other things, now spending eternity living in mind-wracking pain, being kept alive by the Golden Throne he sits on, being forced to watch how everything he built has rotten and become a shadow of its former self... he doesn't have anything left.
Twisted Metal 2 Thumper wins the Twisted Metal tournament, and the driver asks Calypso to make him king of the world... unfortunately, everyone else in the world was killed in the tournament, so he's left sitting alone on his throne.
Final Fantasy Tactics ends with Delita gaining the crown of Ivalice, but his excessive use of manipulation and deceit to get there alienates all his friends and allies. Even his Queen, Ovelia—the woman on who's coattails he rode to get his ass on the throne—is so put off that she concludes she too was just another part of his heartless machinations and attempts to kill him for it. It fails, and he kills her in retaliation. The tragedy—or irony—is increased tenfold in the PSP version, which goes out of its way to remind the player that, yes, indeed Delita loves her and did all this as much for her sake as he did his own.
Disgaea 3: An accidental version of this trope shows up in the Almaz ending. Wannabe-hero Almaz defeats Mao and as a reward Mao's father makes Almaz the new overlord. As a result all his friends (even the princess that Almaz loves) leave him, and the game ends with the new overlord all alone.
Takahisa Kandori of Shin Megami Tensei: Persona accomplishes his goal of becoming a god. By the time you finally encounter him, though, he's in the middle of a Villainous BSOD and has to be needled into fighting you.
At one point in Vampire: The Masquerade - Bloodlines, Prince Lacroix gives a tiresome speech on how he's alone in his position as ruler of Los Angeles and how leadership is so problematic because every other vampire in the city wants him out of the way. He then promptly goes back to treating you like shit.
The second half of Conkers Bad Fur Day, Rare's raunchy Take That to Nintendo's carefully cultivated family-friendly image, becomes increasingly depressing and culminates in Conker becoming king. He's surrounded by people he hates, and he wants nothing more than to go home and have a beer with his girlfriend - but she's dead, because he forgot to bring her back to life when he had the chance. Conker sitting on the throne depressed is how the game opens.
Played unusually straight in The World Ends With You in the stinger ending, where Joshua, The Composer, is standing on top of Ten-Four with Hanekoma. The latter tells him he looks lonely, and Joshua is basically told that he can't join the friends he made over the past month because it's not his world. Cue the White-Haired Pretty Boy flying away before Hanekoma can continue. Talk about a downer ending.
Or maybe he can't join them due to all that time spent murdering and torturing them, while trying to wipe out the whole city. One of those.
Jastor Gallywix defies this in his official short story, Trade Secrets of a Trade Prince. Having alienated the only person he had fallen in love with, and proving that he is scum even by goblin standards, he is still stating that he would not have it any other way.
Hyperdimension Neptunia Mk 2 has an example of this in the Conquest Ending. Nepgear has killed all the other goddesses, including her sister, to power the Sword of Plot Advancement to kill the evil deity, Arfoire. Ultimately, this leads to her accomplishing what every comicbook supervillain dreams of: the world is united under her rule, but all those of her friends who are still alive return to the places they call home, leaving her to rule alone, and she is willing to use "any means necessary" to ensure peace and prosperity.
Nepgear: "This is the dark path that I've chosen to walk alone."
One of the bad ends of Live A Live involves now-Demon King Oersted empowering his incarnations throughout the timeline to kill the heroes and take his revenge of being used and thrown away like how he went through. Credits rolled as Oersted strolls around the now-empty Kingdom of Lucretia, and it ends with him hanging his head low, now completely lonely without anyone, friends or foe from the past, present or future, and doomed with such fate eternally.
Armored Core: Last Raven is literally built around this in a way that you are the last remaining Raven after a day's war. The exact circumstances leading up to it vary depending on storyline, but the hardest path requires you to actively hunt down the other Ravens and be the last man standing.
Dragon Age II - Hawke loses a family member with every step up the social ladder, whether or not you "betray" any of them. In the endgame, several of your True Companions can turn on you depending on whose side you take. The best fit would be siding with the Templars and letting Meredith kill Bethany in the Circle. Congratulations, you get to (temporarily) be Viscount at the cost of the last member of your family. Bethany's last words are even "I hope this was all worth it."
Fate/stay night has several of these characters: Saber, who became a king over a court who has no idea she's a woman and had to throw away all human bonds in order to rule, and Archer, who became the "Ally of Justice" he always strived to be but lost practically everything to do so, was betrayed by his own ideal and was consigned to an eternal Ironic Hell as a Counter Guardian. Shirou also has at least one Bad End where this happens to him. Rin and Gilgamesh, meanwhile, are subversions: They're amongst the best at what they do and have practically no peers or friends as a result of single-minded devotion to their goals, but neither are terribly bothered by it.
Rin actually is bothered by it, her pride however won't let her admit that outside of a single different conversation in UBW... Gilgameshhowever is a true subversion.
At least until the prequel series, when you learn that it's mostly the result of losing the only friend he'd ever made.
This, combined with the obvious communication problems that arise from deafness, is the main reason why Shizune Hakamichi from Katawa Shoujo does not have many friends. She is Yamaku's Student Council President and a Class Representative who takes her responsibilities very seriously and wants to use her position to things to makes the other student's lives enjoyable, but this very same desire makes her come across as bossy to other students and more or less drives everyone else on the Council, including her cousin Lilly, away.
Sinfest: The Devil is devoid of any true friends. The Devil wins a race against Buddha and Jesus, only to end up shut in his empty manor after winning while the 'losers' continue to play around outside.
Homestuck: Subverted with Jack Noir: after he's gained omnipotence, he relizes that he's bored.
Frequently parodied on The Simpsons, where Mr. Burns will mourn how his wealth had made him lonely. Then, ten seconds later, he'll change his mind and decide wealth is its own reward after all ("Money fight!"), or it turns out he was just pretending to be lonely to catch people off-guard.
Moe Szyslak: Rich people aren't happy. From the day they're born 'til the day they die, they think they're happy, but trust me, they ain't.
Homer:[Thinking] Moe. Wish he'd shut up.
Subverted, played straight then subverted again in this exchange
Homer: Let me ask you something: does your money cheer you up when you're feeling blue?
Mr. Burns: Yes.
Homer: Okay, bad example. [beat] So let me ask you this: does your money ever hug you when you come home at night?
Mr. Burns: Why, no.
Mr Burns: Good heavens, Smithers. They're not afraid of me. What good is money if you can't inspire terror in your fellow man?
Azula in Avatar The Last Airbender, a screwed-up young teen in a Big Screwed-Up Family, exemplifies this trope. To gain the love of her father, and compensate for perceived lack of love from her mother, she drove herself to become the most perfect daughter that an Evil Overlord could wish for, and succeeded in style. However, being betrayed by the only two people she had thought she could even begin to call friends when she finally went so far down the evil brick road that even they couldn't stomach following her, eventually being stood up to by her 'weakling' brother, and worst of all, discovering that even after all she'd done her father still wouldn't hesitate to treat her, his supposed 'favorite', as an afterthought to be swept aside and dead-ended in a useless job, she began one of the most epic Villainous Breakdowns in the history of media. When last seen, she'd been defeated by her brother and one of his allies, and was left a broken and desperately frightened child, sobbing and shrieking helplessly in chains before being committed to an insane asylum.
One of the episodes of Teenage Mutant Ninja Turtles consisted of them being thrust into an alternate future of the world where the Shredder has taken it over, turning it into a Dystopia. When they finally meet him, he throws himself at their feet and begs to be taken with them to a world where he doesn't rule, since he had no idea how to actually run the world once he got it.
Pelswick : Used Anviliciously in an episode of which featured an new online school popularity poll. Everyone voted down on each other so that the school bully would be alone at the top. "Can everyone vote down on me so I can be a loser too?" (echo)
Vlad Masters from Danny Phantom falls under this trope. Despite being one of the richest people in the world (Albeit, one who acquired his fame through less-than-moral means), and one of the most powerful as well, he's also virtually alone (save for his cat Maddie and a few random henchmen) and is both painfully aware that he lost the love of his life and a [surrogate] son to his ex-friend.
Happens to Ickis in Aaahh!!! Real Monsters after he finds a stash of toenails (monster currency) ironically owned by a hypochondriac millionaire
Batman ends up this way in the DCAU, as revealed in Batman Beyond. Though he becomes probably the second-best well-known superhero on the planet, his driven personality ends up alienating many of his allies and doesn't take time to nurture human relations. Then he suffers a heart attack and is forced to retire. Until Terry shows up, Bruce has been living as a recluse for some 40-odd years. Alfred died of old age, none of his romantic relationships shown in the earlier series panned out, the bat-family long since split up and retired after Bruce forbade them to be superheroes, and he's too old and bitter to help out anyone else in the superhero biz.
Thankfully he at least gets a loyal son in Terry, who from the looks of things isn't going to leave him high and dry.
Johnny Bravo ran for sanitation comissioner in "Candidate Johnny". He mentioned the trope when he had to clean up the streets by himself for spending the budget on the party held to celebrate his victory.
Freaky Stories once featured a wealthy man who was so estranged from his family and friends he willed his entire fortune to whoever bothered to attend his funeral. The only person who did so was a crasher who had no idea of who he was and only needed the bathroom.
Can be Truth in Television. If you set up a goal in life that has an endpoint, you may find that once you've reached that goal you don't know what to do. It depends on the person though. Generally, if you can't be happy with what you have now and make getting more stuff/obtaining fame/getting political power/whatever a goal to try and fill that void it won't work, but if that stuff is just a part of your life and not the whole point you'll probably think it is pretty awesome.
Howard Hughes, whom Citizen Kane was initially supposed to be based on, died having lived the last years of his life cut off from the outside world due his obsessive-compulsive disorder and general paranoia. He was also a painkiller addict, and his aides intentionally gave him excessive doses so that he would be in a confused state and amenable to anything they wanted to do. All his romantic relationships had failed due to his inability to be faithful, and he'd become paranoid that his accountant and friend was plotting against him.
Funnily enough, William Randolph Hearst, on whom Citizen Kane was based, by all accounts actually lead a much more satisfying life. Hearst apparently realized this was happening to his life and managed to use his money and smarts to avoid it. He created a truly astounding home known as Hearst Castle in Northern California and would invite people he liked to stay. As long as you weren't a dick he would let you stay for months at a time. Not technically buying love and friendship, simply providing one of the best places in the world for it to develop.
Ironically enough, Orson Welles, star of Citizen Kane. Due to his massive ego and oddities, he was essentially blacklisted from working on major Hollywood projects. Fate's a funny thing, particularly considering the above point regarding William Randolph Hearst (although considering Hearst, less-than-impressed with Kane and it's implications about him, was a key figure in getting Welles blacklisted in the first place, it's perhaps not entirely surprising).
However, Welles's ego meant that it was easier to get him blacklisted. Nikola Tesla suffered the same fate since Thomas Edison had superior marketing skills and business knowledge.
Abd-er-Rahman the Caliph of Andalusia did not seem to enjoy supreme executive power all that much:
I have now reigned about fifty years in victory or peace, beloved by my subjects, dreaded by my enemies, and respected by my allies. Riches and honors, power and pleasure, have waited on my call, nor does any earthly blessing appear to have been wanting to my felicity. In this situation, I have diligently numbered the days of pure and genuine happiness which have fallen to my lot. They amount to fourteen.
"No matter how rich you become, how famous or powerful, when you die the size of your funeral will still pretty much depend on the weather." -Michael Pritchard
Barbara Hutton, the heiress to the Woolworth fortune. She was the richest woman in the world during her lifetime, but it was a life filled with chronic loneliness and depression.
deadmau5 has shown this. He has a blog post about not being able to have a "normal" romantic relationship because of his fame, and he's mentioned suffering from depression and anxiety, especially after he broke up with his girlfriend.
By its very nature, becoming an elite, Top of the Anything, means that you are different from the rest, which means that you have less peers.
Enforced by online games which restrict players to only playing against those in their same rank, like Red Crucible 2. If your rank gets too high, you'll find yourself playing the same people over and over, and may miss the huge swathes of unfamiliar people at the lower ranks.