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- While Monster's Tenma is by no means old, he's got a good 15+ years on Johan, who started exceptionally young.
- In Bleach, Yamamoto does battle with Aizen.
- Most of the Captains and Visoreds participating in Fake Karakura town battle are older than aforementioned main antagonist (especially those characters, who fight him directly), who is rather young, but still older than several other heroes.
- Yoruichi fights her former subordinate and student Soifon during the Soul Society arc.
- In Naruto, this happens when the Third Hokage battles Orochimaru.
- Well... Orochimaru's mind/soul/consciousness is at least 50. But his body at that time is young. Though to be fair Even Orochimaru's actual age is younger than the third hokage as he was said hokage's student in his day as a genin.
- This happens to Jiraiya when he fights his former student, Pain. This is even lampshaded when he comments on the irony of Pain treating him like a child when Pain dismisses his views as childish.
- And Minato is also older than his last opponent, Tobi who is actually his student, Obito.
- In One Piece, The 72-year-old Whitebeard fights against both Marine Admiral Akainu (53) and ex-member of his own crew, Blackbeard (38).
- Most climactic fights in Rurouni Kenshin follow this template, as the titular character is a decade older than most of his supporting cast. Specifically comes into play Enishi Yukishiro, his vengeful brother-in-law.
- Mai-HiME has an arc where the various HiMEs who are at youngest middle school age and at oldest full adults go up against nine-year old Alyssa Searrs.
- In Death Note, Hero Antagonist L is 7 years older than Villain Protagonist Light Yagami.
- Legendary Pokémon Mew and its clone Mewtwo from Pokémon: The First Movie.
- Mobile Suit Gundam AGE has a rather twisted example with Flit against Desil.
- In Bakuman。, the clash between Ashirogi Muto and their former fan, the up-and-coming Nanamine. While Ashirogi Muto are fairly young, they also note that they're defending their rank against the newcomers.
- Page vs. Enchu in Muhyo and Roji. Muhyo's quite young himself, although his age is never specified, and he sometimes has to deal with the spirits of those who died in childhood (but depending on when they died, they might technically be older than he is).
- Lyrical Nanoha:
- The old gardener Sul from Kiss Wood defies the authoritarian young dictator Mua in her hellish garden.
- Although he may not necessarily be a strapping young man himself (depending on whether or not you're going by Don Rosa's canon), Evil Counterpart John D. Rockerduck is the younger villain to Scrooge McDuck's older hero. Not to mention Magica De Spell and several of the Beagle Boys. You'd be hard pressed to find a notable enemy of Scrooge who wasn't significantly younger than him.
- Except his better Evil Counterpart Flintheart Glomgold and The Beagle Boys' grandfather, founder and occasional leader Blackheart Beagle.
- This trope could be considered one of the few things that make Rockerduck different from Glomgold: Whereas Glomgold is basically Scrooge as he would've turned out if he hadn't "made it square", Rockerduck is a more modern businessman who is willing to spend away his fortune if it suits him and is sometimes depicted as being more accepted by society than Scrooge is.
- A collection of classic Rockerduck stories mentioned in the introduction that by what passes for canon in Disney stories, Rockerduck is Scrooge's superior in some markets - like media and entertainment, because Scrooge doesn't "get" the concepts well enough to apply his talent for business to it. The usual solution is to rope in his younger relatives, actually needing their advice and not just their underpaid hard labour.
- Happens a lot in comics featuring superheroes from The Golden Age of Comic Books. One of the major reasons why the original Wildcat has a huge fanbase is because of an early issue of JSA, where he took on the Injustice Society alone. With a broken leg. Naked (for the first few pages). This seems to be pretty common for the Justice Society of America these days.
- In the Spider-Man comics, Aunt May has had some of these moments. The most recent was when the Chameleon tried to kill her by pretending to be Peter. She baked him cookies and made him tea, while knitting a nice shawl... and when he revealed himself, she revealed that she'd known all along, and that the "almond" cookies had cyanide in them (actually, just a tranquilizer, but she was feeling mean). The last thing he saw was her holding up the shawl, with "Gotcha!" embroidered on it.
- In the classic comic, Batman: The Dark Knight Returns, the Dark Knight, who is feeling very insecure about getting older, decides to fight the young and inhumanly strong leader of the Mutants hand to hand. As a result, Bats is badly beaten and barely escapes with the help of a new Robin. After he's recovered, Batman arranges a second fight, but this time, he does it intelligently by handicapping the fighting area, using a mudhole to limit his opponent's movements, and using his superior experience in fighting techniques to overcome the villain's physical superiority. Although they are roughly the same age, Superman's perpetually youthful appearance and infinite energy make him look like this next to the battered, aging Bruce Wayne during their climactic showdown.
- Kingdom Come features an entire generation of older heroes doing battle with younger '90s Anti-Hero types. Though in that case it's acknowledged that the older generation is just as flawed as the younger and Both Sides Have a Point.
- In the comic book Sin City by Frank Miller and the associated film, the Yellow Bastard ridicules Hartigan that he is "too old to even lift that cannon [he] is carrying." Of course Hartigan wins the day, and then kills himself after saving the girl, because he's so old it's not worth himself staying alive and keeping Nancy, a young woman, a target.
- In Deathstroke, Slade is targetted by a younger villain, Jannissary, who repeatedly hails him as "old man", but defeats him. Subverted in that Jannissary had been hired for the job, by a man who (accurately) says that Slade is out to kill him; when Slade has Jannissary at his mercy, he explains why. When Slade goes in for the kill, he first returns the money paid to Jannissary and expresses his admiration for Jannissary's principles.
- Technically the case with The Flash and Professor Zoom with the latter being from the distant future, making him a lot younger than Flash.
Films — Animation
- The Incredibles has Mr. Incredible, who's had a teenage daughter during the 15-year Time Skip, battling his young former fan, Syndrome.
- Sleeping Beauty: The younger-looking evil fairy Maleficent vs. the middle-aged heroic fairies Flora, Fauna, and Merriweather.
- In Barbie and the Secret Door, seventeen-year-old Alexa must contend with ten-year-old Malucia.
- Despicable Me is a case of Older Villain Protagonist vs. Younger Villain, with the rivalry between the middle-aged Diabolical Mastermind Gru and his young, smarmy rival Vector.
Films — Live-Action
- From the movie Fried Green Tomatoes:
[Evelyn is cut off in a parking lot]
Evelyn Couch: Hey! I was waiting for that spot!
Girl #1: Face it, lady, we're younger and faster!
[Evelyn rear-ends the other car six times]
Girl #1: What are you doing?
Girl #2: Are you crazy?
Evelyn Couch: Face it, girls, I'm older and I have more insurance.
- Star Wars has it in an interesting way when Yoda is forced to fight his former student Count Dooku. Dooku is eighty years old, but Yoda is nine hundred. Similarly, Anakin Skywalker and Obi-Wan Kenobi dealt with this a couple of times after Anakin's fall.
- Not to mention the example in the page quote, where Darth Vader fights Obi-Wan Kenobi - a man at least fifteen years his senior.
- Qui-Gon Jinn's fight against Darth Maul is also like this.
- Star Trek: Nemesis. Old Picard versus young evil crazy dying Picard.
- The entire Death Wish series, Kersey was always the old man.
- Paul Blart: Mall Cop. After being caught by the Big Bad of the criminals taking over the mall, Paul admits that he was younger, stronger and smarter than he was. And that literally he was the man with the gun.
- There was a minor example in The 13th Warrior, when an old warrior who'd befriended the protagonist gets challenged by a much younger and larger opponent. He proceeds to prove that skill matters more than size or age in hand-to-hand combat.
- The entire plot of Rocky Balboa leads up to Rocky's comeback match against the undefeated 29-year-old champ, Mason "The Line" Dixon, at a point when Rocky himself is just shy of 60.
- In Dragonheart: Bowen, a knight of the Old Code, eventually fought back against his former pupil, Einon, when he became king and showed he was just as vile as his father, if not moreso.
- Morgan Freeman played retired prize-fighter Eddie Dupris in Million Dollar Baby, and for most of the movie he was a kind, soft spoken old man. That is, until one of the younger boxers, Shawrelle, started beating on Danger, a young man with a few mental issues who was basically the laughingstock of the gym. In a Crowning Moment of Awesome, he steps into the ring, reassures Danger that everything is going to be alright, and borrows one of his gloves. Shawrelle mocks him, saying: "Now I get to fight a retard, and an old man! Somebody better call ESPN 'cause you can't write this shit!" Dupris punches him right in the face. Suddenly realizing that he's serious, Shawrelle tries to retaliate, but Dupris' years of experience allow him to easily block, and then he hits him again, with his bare fist, knocking him unconscious. Moral of the story: never assume that just because a man has a soothing voice, he can't kick your ass. Because he so can.
- Live Free or Die Hard is built around this; we get John McClane, the world-weary old-school cop vs Thomas Gabriel, the younger high-tech computer hacker.
- Lethal Weapon 3: Deconstructed very painfully when Murtaugh had to blow away his son Nick's friend, Daryl, in a drug bust after Daryl shoots at him. Murtaugh doesn't take it very well.
- Lethal Weapon 4: Riggs and Murtaugh whom are both reaching retirement facing off against Chinese martial artist and crime lord Wah Sing Ku who is the youngest of the main antagonists.
- The Hunted is all about Tommy Lee Jones having to take down his former student Benicio del Toro who has gone rogue.
- Prime Cut has The Irish Mob's oldest hitman Nick Devlin being sent out to collect a debt from middle aged slaughterhouse owner Mary Ann.
- Has happened a few times through the James Bond film series.
- Being the oldest actor to play Bond, many of Roger Moore's Bond villains were younger that him.
- During Pierce Brosnan's run, the only villain who was older than him was Elliot Carver in Tomorrow Never Dies. Trevelyan from GoldenEye was roughly the same age, and the Big Bad of The World Is Not Enough was, well, different as far as Bond villains go, with a very different dynamic. But Die Another Day plays this trope deliberately, with the Smug Snake Gustav Graves being a younger Shadow Archetype to Bond, what with having his own gadgets, Dark Action Girl, and dangerous exotic lifestyle. His Dragon- about the same age as he is- even has his own Bond car.
- This trope is often used in John Wayne's later films, very notably in True Grit and The Shootist. But even as early as She Wore a Yellow Ribbon you have ageing Nathan Brittles - about to be retired from the army - up against young chief Red Shirt, while bonding with his contemporary, chief Pony That Walks. Red River and The Searchers, where Wayne played characters who are, to say the least, morally ambiguous, invert the trope in a couple of scenes.
- This is the main plot of the second half of Soldier, Kurt Russel manages to defeat a force of younger genetically engineered super soldiers thanks to his decades of combat experience.
- For the loosest definition of "hero", in Jurassic World we have Rexy, the T. rex from the first movie now in her 20's, as the older (anti-)hero vs the I. rex's younger villain in the climax.
- Another loose definition of "hero", in Godzilla (2014) we have Godzilla, who is literally millions of years old, vs the male and female MUTO's, who are only a few days old.
- In Batman v Superman: Dawn of Justice, Lex Luthor is a fair bit younger than Bruce Wayne, with Lex being in his early 30s, plus looking younger, whereas Bruce is in his mid-to-late 40s.
- Pretty much the whole point of Cohen the Barbarian and his Silver Horde.
- Also, the conflict between Granny Weatherwax and Diamanta, in Lords and Ladies. The conflict between Granny Weatherwax and the Queen of the Elves in the same book is an interesting example because the Queen of the Elves, being an elf, is many centuries old, whereas Granny Weatherwax is just an elderly human. However, Granny has learned more through actual life experience. Or as she puts it, "What can't grow can't change. What can't change can't learn."
- Also Death vs. New Death in Reaper Man.
- Sourcery, with the child Coin as the antagonist and adult wizards like Rincewind as the protagonists. Of course, behind Coin is his father, who died of what seems to be at least partly old age at the start of the story...
- In The Hellfire Club by Paul Straub, the female protagonist Nora is around 49 years old. And the Affably Evil Serial Killer villain, Dick Dart, is more than ten years younger than her. Of course, he always had a thing for older women...
- In Harry Potter, Dumbledore can be counted as this until his death and Harry comes into his own.
- In A Harvest Of War 39-year-old Rhona Thyll is the younger villain to her namesake the 58-year-old protagonist and especially the 96-year-old Mayor's older... heroes.
- Galadon and Rhys in Carol Berg's Rai-Kirah Trilogy, albeit very briefly.
- In The Chronoliths Big Bad Adam Mills is a former teenage psychopath and is still young enough to be protagonist Scott Warden's son (he is, in fact, his stepson).
- In Twenty Years After, the sequel to The Three Musketeers, we have Mordaunt (who's in his early twenties) against the titular Musketeers and Lord de Winter (all of them at least in their forties). Possibly a case of Antagonistic Offspring if you interpret Mordaunt as being Athos' son.
- While generally averted in most Watch books, Anton's antagonist in Twilight Watch turns out to be his much younger former neighbor vampire Kostya.
- Murdoch Mysteries: James Gillies, the arch-villain of the show, is a university student in his debut episode, and would therefore be around 20 years old in Season 2. Detective William Murdoch, on the other hand, is approaching middle age.
- Gloriously subverted in with the two main characters. Iconic country singer Rayna Jaymes and younger shining star Juliette Barnes generally don't like and can't stand each other. However, they gradually become warmer to each other as they slowly realize that they are Not So Different.
- Appears inverted but not so gloriously subverted with Rayna's (eventual ex) husband Teddy and her father Lamar. Since both are Corrupt Corporate Executives, Teddy at first was being presented as A Lighter Shade of Black. Eventually, their feud reaches Evil Versus Evil territory. In the end, Teddy watches Lamar die of a heart attack in season 2 and Teddy himself is arrested at the end of season 3.
- The Living Legend Bruno Sammartino vs. evil apprentice Larry Zbyszko in 1980.
- The hardcore legend Terry Funk vs. the nihilistic Raven, from the original ECW.
- The younger outsider Chris Candido vs. company founder and business pioneer Carlos Colon at WWC.
- This was supposed to be the plot of the Bret Hart vs. "Stone Cold" Steve Austin feud during 1996-1997. But fan reactions to them essentially caused the now iconic Face–Heel Double-Turn in WrestleMania 13. Even then, Austin can hardly be considered a hero, thus making it a Gray and Black Morality feud.
- The Undertaker vs. Kane overlaps this with Cain and Abel. Inverted in 1999.
- Brock Lesnar's more profilic feuds have been with older, veteran wrestlers such as The Undertaker, The Rock, Kurt Angle and Eddie Guerrero. Even his infamous feud with Goldberg counts since the seven-years-older wrestler was the face of their feud.
- Ric Flair vs. Triple H in 2002 and 2005.
- Shawn Michaels vs. Triple H from 2002 until reforming D-Generation X in 2006.
- The main gimmick of the Shawn Michaels vs. Chris Jericho in WrestleMania XIX.
- Most of John Cena's feuds during his 2003 Heel run were against older, veteran wrestlers such as Kurt Angle, The Undertaker, Chris Benoit, and Eddie Guerrero.
- This is basically the main premise of Randy Orton's gimmick during his "Legend Killer" days as he challenged older, veteran Faces. He specifically feuded with the likes of Mick Foley, Shawn Michaels, Chris Benoit, The Undertaker and Hulk Hogan. Even during his "Viper/Apex Predator" gimmick, he feuded with his former mentor Triple H.
- Shawn Michaels vs. Edge during late 2004 to early 2005.
- The Motor City Machine Guns vs Bob Backlund and Jerry Lynn in TNA, though it was subverted when the very old Kevin Nash cheated to help the young villains Chris Sabin and Alex Shelley get the advantage during the feud. Later the Machine Guns were the older heroes vs Generation Me.
- ECW Originals vs. the New Breed.
- The aged but locally popular challenger Jerry Lynn vs the younger, cocky foreign champion Nigel McGuinness in Ring of Honor...though the fans seemed to be cheering for Lynn out of sympathy, as they started to turn on him when he actually won the belt from McGuinness.
- Rare three-alignment example: Tommy Dreamer (Old Hero) vs. Jack Swagger (Young Villain) vs. Christian.
- Yoshihiro Tajiri vs a good deal of the roster in his SMASH promotion but The Triple Tails specifically targeted him for his age. However, their first targets were Yusuke Kodama and Makoto, who were both younger than at least one Triple Tail, Kana. Kana changed their targets to "the old men" after Tajiri came to their rescue.
- William Regal vs Kassius Ohno in Florida Championship Wrestling's WWE revival(though the payoff didn't come till 2013 after the promotion was scrapped in favor of NXT). Though it was Regal was the physical aggressor, as he couldn't check his temper to Ohno repeatedly calling him worthless. Chris Hero would later be on the receiving end of this, the older Hero against Trent Barretta in EVOLVE.
- Leilani Kai vs. La Amazona in Ring Warriors, though it was relative, as Kai didn't stop being the dirty cheat everyone knew she was..
- Dave Finlay vs. Sami Callihan in EVOLVE. In this case, it was the "hero" going after "the villain" in an effort to redeem him.
- On March 12th 2012, Cherry had a match at Union Pro Wrestling against her long standing rival, Mio Shirai, with the stipulation being that if Cherry lost, her real age would become public knowledge. It was subverted afterwards when Cherry won but the passport that was being used as her proof of age was stolen by GAMI, who was eventually revealed to be older than Cherry.
- Played with in SHINE, where "The Dinosaur Hunter" Leah Von Dutch was older than two of her targets, not that she realized it. Then averted when she put out an open challenge to the "Shinosaurs", which was answered by Sweet Saraya.
- Team Bad, the younger villain Tag Team vs the 108th District and the Fella Twins in UCW-Zero, not that the latter two were "old" but team bad were teenagers.
- Sting vs Triple H at WrestleMania 31.
- While it's hard to find any unambiguously genuine hero in the Crapsack World of Warhammer 40,000, the Horus Heresy backstory does have the God-Emperor facing off against his favorite adopted son Horus, who has become corrupted by the Chaos Gods, with the Horus Heresy eventually culminating in a duel between the Emperor and Horus, resulting in Horus dying and the Emperor sustaining mortal wounds and being kept kept alive by the Golden Throne.
- In Wrath of the Lich King the Lich King's nemesis Tirion is older than Arthas by several decades.
- In a scenario in Advance Wars II: Black Hole Rising, Smug Snake Adder goes up against Old Master Sensei and starts taunting him concerning his age — shortly before he is soundly whipped by the older and more experienced army commander. Only then does Adder recall the stories of a commanding officer in the Yellow Comet army from many years ago who was said to be unstoppable...
- Even if the age difference isn't that visible between Cloud and Kadaj in Final Fantasy VII: Advent Children, this trope is in effect. Kadaj looks to be in his mid to late-teens whereas Cloud is in his early twenties. In fact, Kadaj (and his brothers) can't be older than two. One of the creators did mention that he wanted Cloud to face someone younger than him.
- On that note, though, Dirge of Cerberus twists this trope into a pretzel....We've got Vincent, our Woobie Anti-Hero, who's 27 physically but had been asleep (which probably means suspended animation) for thirty years, give or take a few, when the original game took place, so he was 57 then. Dirge of Cerberus takes place 3 years later, which makes him 60 chronologically. Confused yet? Now throw in a 25-year-old Omnicidal Maniac who's possessed by a mad scientist assumed to be older chronologically than Vincent himself and if that's not bad enough, just throw in a couple of spirits as old as the planet itself possessing the above and we're into Mind Screw territory.
- In Tekken, Jin vs. Heihachi and Kazuya, and (possibly) the rivalry between Jin vs. Hwoarang.
- EXTREMELY slightly in SoulCalibur, with Siegfried v.s. Nightmare. Nightmare is basically Soul Edge's evil animating armor without Siegfried, and Soul Edge has been around for a LONG time. Siegfried is only in his 20s.
- This happens in Space Channel 5 Part 2. Ulala, who is 22 years old, takes on Purge, who is only 18 years old.
- Assassin's Creed: Brotherhood has the 43-year old Ezio Auditore going up against the 26-year old Cesare Borgia, son of Assassin's Creed II Big Bad Rodrigo Borgia.
- With the exception of Ocelot and Big Boss, the only guyies even older than Snake, Snake in Metal Gear Solid 4: Guns of the Patriots is easily the senior of everyone he fights. And that was before he started to succumb to Rapid Aging.
- Henry Hatsworth in the Puzzling Adventure: Henry Hatsworth looks to be quite a bit older than his rival, Weasleby. He's definitely older than Cole.
- In Professor Layton and the Unwound Future, Layton goes up against Clive, a young boy he saved 10 years ago and who is plotting to destroy London in revenge.
- The Orion Conspiracy: Devlin McCormack is the older protagonist and Captain Shannon is the younger antagonist. The antagonist even insults Devlin's age at one point.
- Ace Attorney:
- In Phoenix Wright: Ace Attorney: Justice for All, 25-year old Phoenix's main adversary in court is Franziska von Karma, an 18-year old Child Prodigy prosecutor.
- In Spirit of Justice, a now 35-year old Phoenix faces off against an even younger adversary in court: Rayfa Padma Khura'in, the 14-year old mystic princess of the Khura'in kingdom.
- The Reveal at the end of the "A Mushroom Kingdom Carol" Story Arc in Brawl in the Family, which explained why the Big Bad of that arc was so strong compared to The Hero. The Bowser that the aging Mario fought wasn't his old rival, but a now adult Bowser Junior. Upon realizing this, Mario takes advantage of his childhood fear of water that he put in him.
"Years of therapy, wasted!"
- In Weapon Brown there are Chuck "Weapon" Brown, the (anti-)hero, and CAL-v.1N, the villain. Both of them are cybernetically enhanced Super Soldiers created by the villainous Syndicate, but Chuck is an older model who has been living out in the hellish post-apocalyptic world for quite some time, while CAL is a newer, more advanced model who is physically a good deal younger than Chuck due to having spend quite some time in the Syndicate's storage as a Human Popsicle. Eventually, it turns out that while some of CAL's enhancements might be superior to Chuck's (such as a better Healing Factor for instance), Chuck's experience with the post-apocalyptic world gives him quite the edge in the end.
- An episode of Gargoyles has Hudson and an injured Goliath playing cat and mouse with a gun-toting Demona. Hudson's plan is eventually revealed to be: hide just out of sight and let her yammer on till the sun came up. Despite what it looks like, this is actually something of an inversion — Demona is really several centuries older than Hudson, thanks to magical eternal youth on her part and a case of suspended animation on his, so she has both the advantage of centuries of experience without the disadvantages of aging. Hudson's victory is instead thanks to Demona's Immortal Immaturity. Whereas Demona has spent her centuries in a vicious cycle of rage, distrust and betrayal, Hudson made peace with life and found wisdom.
Hudson: I know how to wait.
- Youngblood mostly plays this role in Danny Phantom where his spunky, immature attitude clashes with Danny's teenage maturity. This becomes key in one episode. Because Youngblood can only be seen by children, Jazz doesn't realize he exists because she thinks like an adult despite being sixteen. Danny however, takes inspiration from Youngblood's bratty, childish behavior and starts behaving like an Annoying Younger Sibling, rendering Jazz to start throwing a tantrum and embracing her childhood, and importantly, spotting Youngblood. She then helps Danny kick his ass.
- Parodied in Futurama with Professor Farnsworth's Rival Ogden WEEEERNSTROM!! constantly calling the 160 year old Professor "old man" etc, in keeping with this tropes style. The twist? Wernstrom is "merely" 120. Yeah, he's only slightly less ancient.
Wernstrom: Go home before you embarrass yourself, old man! Now if you'll excuse me, I'm going to take a nap before the ceremonies.
- In the obscure Canadian series Zeroman, Rusty was probably young enough to be the hero's grandson.
- In Winx Club both Griffin and Faragonda have a example. Griffin in Season 1 when she fought the Trix for Cloudtower, but loses. Faragonda in Season 3 when she fought Valtor, but she loses too.
- Multiple episodes of Batman Beyond have 80-year-old Bruce Wayne taking on younger villains: The Jokerz, Inque, The Ts, Big Time, etc.
- In Gravity Falls, Stan Pines, a man old enough to be a great uncle, has a business rivalry that later turns violent with Gideon Gleeful, a nine-year old.
- Duke Igthorn of Adventures of the Gummi Bears is obviously a lot younger than his primary rival and target King Gregor, whose kingdom he's always trying to conquer, and usually calls him "old man" whenever they cross swords.