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One is that the older character doesn't fall out of the Competence Zone because they're under the direction of the hero, and thus doesn't undermine the maturity of the younger hero. If the relationship is close, the sidekick's more adult personality actually fulfills some parental role, which the hero might lack from having no family, without being intrusive. On the other hand, the Older Sidekick can be a non-threatening yet incredibly appealing fantasy object for the audience, who identifies with the main hero. A variant of this is when the younger character leads out of status or rank but requires the more experienced sidekick for advice. A typical example of this would be Captain Smooth and Sergeant Rough.
Another is that the main character may be too young or small for physical power. Their expertise lay elsewhere, thus the Older Sidekick also is the Battle Butler who goes everywhere the main character does, instead of merely staying home and guarding/minding the house. Often, in these cases, there only appears to be an age difference, or the age difference is the opposite of what it appears so it's not as hard to justify them hanging around each other.
A related dynamic is when the two characters have a (increasingly) full equal partnership, but there's just enough of an age difference to create protective feelings in the older one. Usually both characters are designed to appeal to different segments of fandom, and the story will end up using many designs that end up appealing to shippers (compare Seme and Uke). Think a more intimate version of the Buddy Cop dynamic.
In fact, the Older Sidekick is very handy for lessening the perceived Squick of shipping the characters, as the audience seem much more willing to rationalize that the characters are on equal ground.
Anime & Manga
- Tuxedo Mask, Sailor Moon's college-age boyfriend. He starts out as the Mysterious Protector, but quickly falls into sidekickdom by the end of the first season. Note that he's college-aged in the anime, whereas in the manga he still was attending High School.
- Vampire Princess Miyu's minion Larva was eventually revealed to be an incredibly attractive man underneath his mask, and due to fan pressure, we saw it much more frequently.
- Renamon and Ruki in Digimon Tamers. Their relationship is more of being actual contemporaries rather than a pet or babysitter dynamic, although this is probably more conductive to Ruki's original cold professionalism.
- A Message In The Packet takes it even further: Ruki calls Renamon her big sister several times in her message.
- Digimon Tamers actually has a number of these, since the series takes place (mostly) in the real world rather than the digital one. In the latter parts of the series, the kids are backed up by the middle-aged Monster Makers, as well as man in black Yamaki and his Hypnos organization. In fact, their ultimate triumph can be attributed fairly equally to the efforts of both children and adults.
- Villain example: Nappa is the older henchman to Prince Vegeta in the Saiyans arc of Dragonball Z. However, Vegeta was much more powerful than him, and quickly killed him when he was unable to fight anymore.
- Bee Train became famous for its "Girls With Guns" dynamic, usually featuring a hot, confident older woman partnered with a younger, shorter, but still quite capable girl.
- Lumeire and Eclair from Kiddy Grade are also an apparently older/younger girl duo. Many of the partner couples of the GOTT are like this in the series.
- Alyssa and Miyu from Mai-HiME. (Well, at least so it seems. Since Miyu was an android built specifically to protect Alyssa, the latter was technically slightly older.)
- Evangeline and Chachamaru in Mahou Sensei Negima, though only in appearance (hundred-year-old vampire and two-year-old Robot). Negi and Asuna (and his other partners) along with Chamo are definitely played straighter.
- Mythical Detective Loki Ragnarok has Yamino Ryuusuke, who looks ten or fifteen years the title character's senior, and is Loki's frequent sidekick, butler, housekeeper, voice of reason... oh, and son.
- In Chrono Crusade, Rosette tends to introduce Chrono as her assistant. In his usual form he looks to be a young teenager a few years younger than her, so this doesn't seem too odd at first, but in reality he's a demon who is actually closer to 90 years old. In his demon form, he looks closer to a man in his twenties and is much taller than her. And yes, he's very protective of her, and yes, they're the series' Official Couple.
- Arf of Magical Girl Lyrical Nanoha for Fate, though considering how she's a wolf familiar that Fate bonded with, she may be Younger Than She Looks (well, when she's not using her Fun Size mode).
- Arf, despite having been created two years before the original series, is "officially" 16 in the original series, having been a familiar long enough to attain an adult form, and tends to consider those in Fate's age group younger than she is.
- A straighter example is the Wolkenritter of Hayate, most of whom are not only older than Hayate in appearance, but they're all a lot older than her in age.
- Pop from Dai no Daibouken is a few years older than the protagonist Dai.
- Despite his 11-year seniority, Kisame from Naruto acknowledges his junior partner Itachi as the strongest of the duo and does everything he says without question. So that would indeed make him the sidekick.
- Though there are many fans who don't want to think of it this way, Kamina of Tengen Toppa Gurren Lagann is really just an Older Sidekick to the true main character, Simon.
- They're Bash Brothers who are true equals, both excelling in the areas the other lacks in. Simon later outgrows Kamina, making the latter seem like an older sidekick in retrospect.
- Fullmetal Alchemist: To those who don't see him as a Big Brother Mentor, Maes Hughes is this to Roy Mustang.
- Also, the manga gives us Fu, one of Ling's bodyguards. Fu looks 60 or 70, and Ling is only 15. Justified in that Ling is a prince, and Fu's entire family serves the royal line.
- Sven Volfied of Black Cat is both Train's Older Sidekick and the Team Dad. His primary role (aside from kicking ass when necessary) is to be the voice of reason, maturity, and emotional stability, as Train's mental age is about 12 and Eve is discovering what emotions are.
- Rangiku Matsumoto serves as Toshiro Hitsugaya's lieutenant in Bleach, despite her being older and having been a Soul Reaper longer than he has.
- The Golden Age DCU had the Star-Spangled Kid and Stripesy, his adult sidekick. This was brought back in The Modern Age of Comic Books in Stars and S.T.R.I.P.E and also in Justice League Unlimited, although the potential squick is reduced because her sidekick (the original Stripesy) is her stepfather, tagging along to keep her out of trouble.
- Jon Sable's old fencing coach Sonny Pratt appointed himself to this role in Jon Sable Freelance.
- Back in The Golden Age of Comic Books, a lot of superheroes had older Plucky Comic Relief sidekicks. The best remembered today is probably Doiby Dickles, the cab-driving associate of the original Green Lantern.
- Another example would be Uncle Marvel, adopted uncle of Captain Marvel.
- Actually, the entire Marvel Family is older than Billy.
- In the 1989-93 NOW Comics comic book adaptation of The Green Hornet, Hayashi Kato (sidekick of the second Green Hornet, based on the Bruce Lee role in the 1966 TV adaptation) becomes Older Sidekick to Alan and Paul Reid (the third and fourth Hornets, respectively).
- Digby, Dan Dare's Plucky Comic Relief sidekick.
- Rayek in Elf Quest has Ekuar, who can kick ass with a twinkle in his eye despite years of slavery, torture and mutilation at the hands of the trolls.
- Rip Hunter and Booster Gold are an interesting case. Since Rip Hunter is the leader of the Time Masters, Booster could be considered his sidekick -- except he's actually Rip's father later in the timeline. Rip, in turn, is advised by the older Booster from time to time.
- Captain Haddock, Tintin's sidekick, starting in 1941.
- Vampire-hunter Blade had Whistler, who started out as an older mentor, but fell into the sidekick once Blade surpassed him.
- Sid Waterman (Woody Allen) to Sondra Pransky (Scarlett Johansson) in Scoop.
- Han Solo to Luke Skywalker in Star Wars, where the older, more worldly (and cynical) Han serves as a foil to the younger and more idealistic Luke. Later they develop a older/younger brother kind of relationship.
- In Books 3 and 4 of The Faerie Queene, the only female knight, Britomart, is accompanied by her old nanny, Glauce, disguised as her squire.
- In The Wonderful Wizard of Oz, Dorothy is a child of about 9-12 years old. The ages of her companions tend to vary by adaptation or interpretation. Going by the book, though, Nick Chopper (the Tin Woodsman) was a full-grown man before the Witch's curse caused him to become a steampunk cyborg.
- Amped up in Tin Man where DG is explicitly stated to be 20 "annuals" old. Glitch and Cain are easily 15-20 years older, the former being an obviously long-term adviser/old friend to her mother, the latter having a son roughly DG's age.
- In the third and fourth Alanna books, having won her shield, Alanna goes out to roam the world. Her only travelling companions are her cat Faithful and Coram, technically in her employ, but more or less a father figure.
- Artemis Fowl is always accompanied by his Battle Butler (known, self-descriptively, as Butler). The author justifies the name as the fact that one of Butler's ancestors may have been the person whose name became the title of the profession. This is a case of Did Not Do the Research, since Butler comes from the Old French word for "wine bottle" by way of the Anglo-French word for cup-bearer.
- Modern-day paladin Michael Carpenter plays this role whenever he pairs up with Harry Dresden in The Dresden Files
- This is Older Than Feudalism: In Homer's The Iliad, Patroclus was traditionally an Older Sidekick (and, later, the ultimate Dead Sidekick) to Achilles, although modern adaptations such as the movie Troy tend to portray him as younger to be more in keeping with audience expectations.
- Sergeant Lewis to Inspector Morse in the original novels.
- In Harry Potter, both Ron and Hermione are - albeit slightly - older than the title character.
- Marc to Jame in PC Chronicles of the Kencyrath.
- In The Chronicles of Prydain, Fflewddur Fflam is the Older Sidekick to Taran and Eilonwy, who are barely out of their teens. He subverts the expectation that he would be more mature and responsible than them, however, being something of a romantic and a daydreamer (although he's still handy in a fight).
Live Action TV
- Former spy Michael Westen of Burn Notice frequently calls for assistance from his best friend, retired Cold Warrior Sam Axe, who generally enjoys the opportunity for adventure.
- On an episode of Hercules: The Legendary Journeys, it was revealed that Iolaus is actually older than Hercules by two years.
- Rather odd considering that in the myth, he's Heracles' NEPHEW.
- Captain Jack Harkness to the Doctor in the Doctor Who two-parter "The Stolen Earth"/"Journey's End". After being trapped under Cardiff for 2000 years in his spinoff show Torchwood, he's now twice as old as the Doctor, who claimed to be 903 around that time.
- Though naturally much younger than The Doctor, Wilf in The End Of Time certainly looks the part, being the Doctor's oldest human companion.
- In series 5, Rory Williams became this, being an Auton replicant with Rory's memories, standing by the Pandorica for 2,000 years. Though by the end of "The Big Bang", he's now back in his twenties, with his millennia of memories locked away unless necessary.
- John Watson in BBC's Sherlock
- Dorota to Blair Waldorf on Gossip Girl.
- "Hop hop, Mr. Bubbles!"
- K' from The King of Fighters has Maxima, who has to keep his younger partner's temper in check at times.
- Cloud, the Hero, and Barret, the Lancer, from Final Fantasy VII. Barret is fourteen years older than Cloud. Interestingly, neither of them are particularly mature - Cloud spent his formative years in a People Jar and has the emotional maturity of a sixteen-year-old as a result, and Barret is emotionally driven to the point of completely neglecting to think his actions through. They seem to cancel each other out.
- Metal Gear Solid does the equal-partnership-with-paternity-and-fan-service thing, and (oddly for the series) it's played straight and isn't deconstructive. Raiden is the Bishonen, and the main character. Snake is a Cool Old Guy, the side character, and mentors Raiden. Both are very sexy.
- Both of the sidekick NPCs from Beyond Good and Evil are significantly older than the 21-year-old protagonist Jade. One of them is her middle-aged "uncle," the other is a soldier in his mid-30s.
- Pint-sized sixteen or twenty-one year-old detective Johnny Garland has an older sidekick in the form of Battle Butler Lenny in the game Shadow Hearts: From the New World. He's also the youngest member of the party. He's not alone, either: Shania has Natan as a bodyguard, and Hilda has Roger Bacon, although the two of them would disagree on which is the sidekick.
- Phoenix's regular partner in the Ace Attorney saga is his young assistant Maya Fey, but when he needs extra assistance he calls Maya's older sister Mia fey, who fits in this trope. Also, Mia's assistants were her mentor's Marvin Grossberg and Diego Armando, both older than her. Then Apollo was assisted in his first case by his mentor Kristoph Gavin, and later Phoenix himself, and finally in the Spinoff Ace Attorney Investigations, Edgeworth will be helped by the older Detective Gumshoe.
- The obscure platformer Scaler has the Kid Hero Scaler assisted by Leon, a jowly lizard-man with a Giant Flyer. While they don't exactly get along well at first, eventually they take a shine to each other. Good thing, too, since Leon is Scaler's long-lost father.
- Raidou Kuzunoha vs. the Soulless Army has Talking Animal Spirit Advisor Gouto-douji, who is over a thousand years older than the eponymous protagonist.
- Sengoku Basara has two instances of these. First is Date Masamune's Battle Butler Katakura Kojuro, who has a good ten years on his master and is implied to be somewhat stronger, and second is Sanada Yukimura's Ninja Sarutobi Sasuke. Both examples also play the part of the Hypercompetent Sidekick to their rather young and inexperienced leaders, serving as a calmer counterpart to the Hot-Blooded teenagers. Incidentally, both masters and sidekicks are rivals to one another.
- Donald Duck and Goofy to Sora in the Kingdom Hearts series. While they're Funny Animals who don't really have a set age, they're still pretty much adults.
- Baldur's Gate has Jaheira and Khalid, two sensible elves and old friends of your foster father. While you don't have to bring them along (or even meet them at all, if you so choose), they are canonical in the sequel, not to mention that you're given explicit instructions to seek them out.
- Fallout 2 has Cassidy. Though his character model lacks the detail to confirm it, he is firmly established to be in at least his late fifties. Marcus would also qualify; his Super Mutant status has made him stop aging, but her served in the Master's army during Fallout 1--eighty years previous.
- RL-3 and Charon from Fallout 3 technically qualify (Charon is a nuclear mutant who could be as old as 240, while RL-3 is a model of robot that hasn't been in production for 200 years), but it is more obvious with Star Paladin Cross. Cross mentions to the player that she carried you once, when you were a baby. Jericho will also refer to himself as an old man, especially when the player recruits or fires him.
- As in previous examples, Raul and Lily from Fallout: New Vegas. While Raul and Lily have the same age-defying abilities as Charon and Marcus (respectively), they come across as much older because of Raul's constant referring to himself as a feeble old man (and his loyalty quest hinging on it), and Lily's mental instability leading her to mistake the Courier for her grandchild.
- Avatar: The Last Airbender: Not only was Aang the youngest member of his trio in the first season (sort of), but the cheerful and experienced General Iroh is the foil to the bitter but complex teenage Anti-Villain Prince Zuko.
- In Mighty Max, the titular hero is a twelve year old boy so he has his Body Guard Norman do all the killing. Meanwhile Virgil who is even older, serves part as his boss (telling him what needs to be done) but more as a sidekick, helping him out and giving him details he'll need to know.
- Jake in Adventure Time.
- Hudson to Goliath in Gargoyles
- It used to be the other way around, but Hudson chose to step down from the leadership of the clan due to old age.
- Joe Biden, Vice President to Barack Obama. Before him, Lyndon Johnson, Vice President to John F Kennedy.
- Then we have Dick Cheney's vice presidency to George W. Bush.