The old men from Gun X Sword. They keep drinking and talking about the Glory Days in a deceased member's granddaughter's tavern and get chewed out by the other people who don't even believe them. They prove themselves again when an armor attacks their town and they get to show off the El Dorado V.
The singular most painful recent example would have to be from the 2003 Utsuge turned AnimeKimi Ga Nozomu Eien. Hayase Mitsuki, a once-in-a-generation swimming prodigy had the makings of an Olympic-Grade Champion, only to leave it behind to look after her best friend Haruka's boyfriend Takayuki, so suicidally depressed over his love's car-accident induced coma (inadvertantly caused by Mitsuki) that he could not finish high school, and took Takayuki for herself. Three years on, when Haruka awakens, Takayuki virtually leaves Mitsuki behind to restart life where he left it behind. Adding insult to injury, Mitsuki (now a mere office lady) meets an old-rival who is now an olympic grade champion-swimmer herself, doubly reminding her of the meaninglessness of her sacrifice.
In Death Note, Light Yagami kills L at the end of the first arc, in his Crowning Moment of Awesome, then spends the rest of the series, and his life, missing the challenge from L and working at a desk.
What? When did he ever say 'aw, I miss my opponent'? He's ruling the world pretty much and he's happy with it. He doesn't want a rival to take his godhood away.
This example is odd but legit because, while Light is consciously very pleased with events and doesn't seem aware of his own deterioration, he's just not enjoying life anymore; it's back to the way it was before he found the Death Note, only on a bigger, more satisfying scale. And to the readers it's painfully obvious that he's gone to seed.
He mentions repeatedly that Near is nothing like L was. On that note, Near is a subversion as he refuses to call the Death Note user in the extra chapter Kira because it would insult the Kira of his glory days.
And since he's all but running the world, as well as the investigation to catch, well, himself, Light is just so far ahead it's boring. L was his intelectual equal and while Light didn't appreciate the threat of being caught the challenge was clearly half the fun of being Kira for him and while the others give him a challange, Light is too many steps ahead for them to be a challenge.
Cowboy Bebop has a trio of old men (possibly former cowboys) which keep talking of the great days back in their youth.
In Nextwave, Monica Rambeau can't start a sentence without mentioning how she once led The Avengers.
Most of the depowered heroes in JLA: Act of God seemed to not be able to get past the days when they were superheroes. Even Supergirl called the past, 'The Glory Days'.
Producer David O. Selznick had his greatest hit with Gone with the Wind. He made hits after that, but nothing on the level of that movie, which still tops Titanic when adjusted for inflation.
In Galaxy Quest, the main character suffers from a brief Heroic BSOD at the beginning, when he overhears someone laughing at the fact that he and his colleagues haven't had an acting role since the titular Star TrekFictional Counterpart a decade or two earlier.
Until then, that Large Ham had been happily Chewing the Scenery and enjoying having fans; the rest of the cast were long-since sunk in awareness that they were washed up and abiding hate for their 'captain' coworker. (William Shatner approves this message.)
Uncle Rico from Napoleon Dynamite is a particularly sorry example of this trope, as he looks back on a football game that he spent warming the bench. He spends all his free time practicing his throw and lamenting that he could have won the game and gone pro if the coach had put him in.
He even buys a "time machine" on the Internet so he can go back and change his life.
Played with to the point of subversion in Music and Lyrics; whilst former pop-star and professional has-been Alex Fletcher's Glory Days are well and truly behind him at the beginning of the movie, unlike many of the others on this list he is, if not exactly ecstatic with his lot, then at least comfortably resigned to it. Having found some measure of contentment in the low-rent theme-park gigs he does to support himself and the middle-aged women who still flock to watch him, he doesn't really demonstrates any burning desire to get back to the old days, and seems to have accepted the fact that his Glory Days are behind him and that he's a bit irrelevant, as his main motivation throughout the movie is not to get back on the charts, but to make sure he gets a sufficient enough profile to secure a lucrative contract singing at Disney Land.
In This Is Spinal Tap, the titular band spend most of the movie actively determined to pretend that the Glory Days aren't well and truly behind them, despite the fact that the crowds and venues are getting noticeably smaller.
While the subplot with his daughter is clearly drawn from Jake's life, the rest is every third ex-wrestler you care to name. People in this business do not deal well with aging.
Subverted in that after September 12th, 2008, "The Ram" is actually better, while broken down/living the poor life, than Jake Roberts. EGAD.
Sam Rothstein laments the old Vegas at the end of Casino.
Robert De Niro's character in The Fan, to an Axe Crazy degree.
The Teenage Mutant Ninja Turtles were going through this in TMNT, which is odd, since there was no indication from the last movie that things would turn out this way.
The latest Rocky film was also meant to remedy such a situation caused by the 5th film.
"Fast" Eddie Felson in The Color of Money. We saw his Glory Days in The Hustler but when The Color Of Money opens, he's a bitter burnout selling booze and ends up working as a stakehorse to a younger player. Subverted when he makes a comeback towards the end of the film.
Mr. Incredible from The Incredibles exemplifies this trope. After a forced retirement from his career as a super-hero, he settles down and becomes a typical cubicle dweller. While his wife has adapted to their new circumstances, he is stuck re-living his past glories, a fact which the villain exploits to get Mr. Incredible to unknowingly help him.
Helen: Risking our family again so you can relive the glory days is a very bad thing!
Bob: Well, reliving the glory days is better than acting like they didn't happen!
Parodied in Hamlet 2; Elizabeth Shue plays herself as a survivor of the Hollywood Hype Machine having decided to quit acting and become a nurse instead. The main character is a huge fan of hers and invites her to the school to give a talk about acting to his drama class — which ends up embarrassing for all concerned, as the kids have no idea who she is.
One of the main themes in The Turning Point. Emma was once a great dancer, but now she's in her mid-forties and can barely execute a double pirouette. Her old friends Wayne and Dee Dee, also once on their way to ballet stardom, abandoned their performing careers shortly after having their first child. And Michael, the artistic director, has devolved from a great choreographer into an administrator.
Literature
Tan'elKoth in Blade of Tyshalle literally fits this trope to a T. He used to be a god. As a line points out, his very name was changed to an unwilling admission that he no longer is that being. Hari also longs for the glory days of his career, when he was an unstoppable assassin instead of a paraplegic bureaucrat. See also Orbek's obsession with reviving the Black Knife nation in Caine Black Knife
Many characters in The Great Gatsby, but especially Tom Buchanan, who used to be a star football player for Yale. Nick's impression of Tom is as a restless man who goes about his entire life looking for another football game to win.
Gatsby himself inverts this. He never had such pure happiness in his past, but he's ignoring reality in order to try and make the future glorious and perfect and lovely.
Subverted in Children of the Lens, last in the Lensman sequence: the surviving crew of the battleship "Dauntless", now top brass, cast off their regalia and revert to their original roles aboard ship of twenty years before in order to re-enter a strange universe and craft the ultimate weapon. They literally get to relive their glory days, even as they are living a second set.
Live-Action TV
A witch in an episode of Buffy the Vampire Slayer (who didn't see this coming) never got over her glory days as a cheerleader, so forcibly switched places with her daughter to relive "her glory days".
Star Trek: The Original Series, episode 2x24, "The Ultimate Computer," had Dr. Richard Daystrom and the duotronic computer system. Years later, he did get a prestigious science academy named after him.
Did you know that Al Bundy of Married... with Children once scored four touchdowns in one game of high school football? Al sure wants you to know.
Illyria, a Cthulu-esque goddess demon from Angel, awakens from millions of years of stasis to find herself trapped in a human body, her cult all but extinct and her armies long since turned to dust. She spends a lot of time moping about how powerful she used to be. It's actually quite poignant to see how she deals with the modern world.
It's amazing that Ducky has even had the time to experience all the things he's always rambling on about. He's not that old...
Q: How many Centauri does it take to change a lightbulb?
A: Just one... but in the Glory Days of the Republic, hundreds of servants would change thousands of lightbulbs at our every whim!
The main theme of The Twilight Zone episode "The Sixteen Millimeter Shrine", in which aging actress Barbara Jean Trenton longs for the days when she and her friends were young, beautiful stars.
Highlander actually has an episode called 'Glory Days', where Joe Dawson, who was the star quarterback of the high school football team, meets up with the head cheerleader he'd once dated for a time. He gets depressed because of having lost his legs in Vietnam, and doesn't think she'll like him, that he's 'damaged goods' (she was actually married anyway, and nothing came of it, but she does reassure him that he isn't damaged). Meanwhile, Mac is targeted by a former mobster immortal who's also this trope, depressed and unhappy and wanting Mac dead for instigating the 'death' that got him kicked out of the mob back in the 30s.
Mike Oldfield - After the surprisingly huge success of his debut album "Tubular Bells", he tried to reproduce it again, again and again to save his decreasing popularity, which didn't help much.
He's ruefully acknowledged that last one in interview - that somehow, going back and fixing it has wrecked it.
The Bowling For Soup song "1985" is about a woman who misses her high school days back in the 80's.
The Bob Seger hit Like a Rock features a man reminiscing about his youth.
Mythology
Jason from the Argonautica actually met his end because of his obsession with his Glory Days. After Jason's lack of faith to Medea destroyed his life, he found himself years later on the beach where the hulk of his old ship the Argo lay. As he sat reminiscing about his adventure, the rotting prow of the Argo fell on Jason.
Theatre
Willy Loman in Death of a Salesman is so obsessed with his glory days that he occasionally flashes back to them.
This is a major element in the story. In fact, the trope in terms of whether or not the glory days actually had that much glory in them, or was Willy (and also his son) unknowingly reimagining their past because they could not stand the idea that they never were anything big in the first place.
Video Games
Guybrush at the start of Monkey Island 2: LeChuck's Revenge. Since he beat LeChuck in the first game he had a great life, but people were expecting more and eventually he lost Elaine and the people forgot about him. It was one of his motivations to find the Big Whoop.
Web Original
In Survival of the Fittest, it's often argued that Version 1 was the Glory Days of the board, and that people much prefered the old systems and the ways of going about things. Fortunately, with V3 underway, this dissension appears to have died down. New Glory Days perhaps?
Depending on where you stand, this was subverted in a recent thread on the board, in which both V1 and V2 were criticised - V1 for being too spontaneous and for a lesser writing quality, and V2 for being too overplanned. To quote the Admin of the site, "for the most part, V3's found a good mix of both planning and spontaneity". Read the thread here.
The main theme of There Will Be Brawl. Mario, Link, and a few other characters in particular seem to have taken it hard.
Western Animation
Camp Lazlo: on the episode "Dead Bean Drop", Slinkman, of all people misses his days as a death-defying daredevil, but he seems to have shoved it into the back of his mind over the years until Lazlo, Clam, and Raj find out and begin talking about it nonstop. He apparently moves past it when after fifteen years of having quit, he manages to jump the titular cliff, and it is never mentioned again.
Some people in the United States when it comes to World War II. Now both the left and the right agree it was a good thing we were involved. The problem is trying to use in the way of other examples of this trope.
