1. The two guys do not have to be physically stronger or weaker than the other to fit this trope.
2. This trope applies to personalities as much as physical strength or appearance. Two guys can be strong and if one acts sensitive and the other acts manly, then they fit.
3. The sensitive guy does not have to possess more feminine traits than masculine traits.
4. If you post an example that may not be so obvious, be sure to explain how one is a sensitive guy and how the other is a manly man.
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Anime and Manga
Randy McLean aka Ryo and his partner and eventual boyfriend Dee Laytner from FAKE.
Bleach plays this trope straight with Ichigo (manly man) to Uryuu (sensitive guy), Hanatarou (sensitive guy) and Ganju (manly man), Love (manly man) and Rose (sensitive guy), and Hisagi (manly man) and Kira (sensitive guy). However, it plays with the trope in other ways.
Sado is a huge, physically powerful man who is a Technical Pacifist and Gentle Giant. As such as he plays the Sensitive Guy to Ichigo's rough tough guy act.
Hisagi and Kira are subverted during the Fake Karakura Town battle when dealing with an overly emotional Yumichika. Hisagi takes the Sensitive Guy route of attempting to talk Yumichika down. Kira doesn't bother and simply tranquillises Yumichika into unconsciousness, disapproving of the way a fifth seat was talking to a lieutenant.
The anime plays straight with Ikkaku (manly man) and Yumichika (sensitive guy) through a considerable softening of Yumichika's character. There's something of a subversion going on in the manga and databooks: Ikkaku's good at meditation and inner communion and was more in touch with Kenpachi's feelings than Yumichika. Yumichika's true idea of beauty is that only flowers are beautiful and people can only achieve it at the moment they're torn to death. While Ikkaku merely told some slackers they were idiots for getting caught, Yumichika told them he'd kill them if they didn't do a perfect job. Lampshaded when Yumichika and Ganju fought where Ganju played sensitive guy to Yumichika's aggression by observing how sadistic Yumichika's personality really was.
Kugo Ginjou and Shuukuro Tsukishima. Ginjou has the masculine, muscular "bad boy" look and rough personality and fights with a a huge broadsword. Tsukishima tends to come across as more elegant, Bishōnen, fights with a sleek katana and behaves more politely. However, like the Ikkaku/Yumichika dynamic there's a partial subversion going on where Ginjou has more of a "what you see is what you get" roughness to him who has to try and keep in check Tsukishima's apparent sadistic enjoyment of breaking the minds of his victims which he hides under a civilised veneer that's only skin-deep.
Mahou Shounen Majorian blurs the line between this and Tomboy and Girly Girl with Iori and Masaru. Iori is extremely feminine in appearance and manner, and Masaru is a typical boy who plays sports and doesn't like girls because he has four obnoxious sisters.
Then they're both turned into magical girls by aliens who mistook Iori for a girl. Naturally, Masaru has a huge problem with that.
Simon and Kamina are like this at the start of Tengen Toppa Gurren Lagann. By the end of the series, Simon grows into the Manly Man role fantastically. Kamina even says that Simon's become more of a man than him during Simon's time in the Lotus-Eater Machine.
The Irresponsible Captain Tylor plays this straight for laughs early on. Two terrorists seize a building, one of them an effeminate "sensitive guy" and the other one more traditionally manly, despite being an alien.
Sort of inverted in The Prince of Tennis with the doubles pair of Ohtori and Shishido. Choutarou Ohtori, the taller, physically stronger of the two, is sensitive and nice (he even plays classical violin and wishes for world peace), while Ryou Shishido is shorter, louder, bad-tempered and much more butch (he even has the scars to prove it!).
Another subverted example would be Seiichi Yukimura and Genichirou Sanada. The first is polite, soft-spoken, with a frail health and long hair...; the other is very tall, stern and the Kendo Team Captain in a tennis setting. The subversion comes from Yukimura being the captain of their team as well as a Knight TemplarMagnificent Bastard when it comes to tennis, and Sanada being extremely devoted to Yukimura - like a Samurai's devotion to his feudal lord (and yes, they're one of the most popular Ho Yay couples in the fandom).
Hiroshi Yagyuu and Masaharu Nioh play it a bit more straight... unless you count the manga, where they impersonate each other perfectly)
It can be said that every doubles pair, rival pair and/or captain and vice-captain duo plays around with the trope in different degrees. Tezuka and Fuji, Tezuka and Oishi, Oishi and Eiji, Momo and Ryoma...
Sort of subverted and followed for Hidan and Kakuzu from Naruto. Kakuzu is the thoughtful, more articulate, less aggressive and more strategy-based man of the duo. But he is stronger than Hidan, and he looks more manly. Hidan, on the other hand, is overly aggressive, loves to cuss and insult, and is very confrontational and arrogant. They certainly bicker a lot, and quite a bit of it has to do with Kakuzu getting annoyed with Hidan being rash and not thinking things through, with Hidan thinking that Kakuzu is a wuss that's too reserved. All in all though, Kakuzu would generally be the Sensitive Guy and Hidan would follow the Macho Guy role.
In recent flashbacks, Nagato who later becomes Pain is the Sensitive Guy to the Manly Man Yahiko.
Recent flashbacks also show that Hashirama and Madara started out this way too. Hashirama is the Sensitive Guy to Madara's Manly Man
Code Geass: Played with with Suzaku and Lelouch, especially in the sound dramas. Lelouch is much more feminine in his tastes and appearence while Suzaku is far more masculine. Yet of the two, Suzaku seems much more kind and sensitive than snarky, aloof Lelouch. Of course, Code Geass being the universe it is, this gets deconstructed. As children, however, they played this trope straight as Suzaku was rough, boisterous, and a bit cruel whereas Lelouch was sensitive, sheltered, and more gentle.
Ryu and Joe in Science Ninja Team Gatchaman, sort of. Ryu is definitely the softer-hearted of the two but is far from "in touch with his feminine side". Joe is definitely a guy's guy but in a more grizzled way rather than oozing testosterone. Ken and Joe's dynamic is sort of a subversion; Ken only looks the part of the doe-eyed sensitive one, but it's his repression of emotions that leads to some rather ugly outbursts.
Subverted with Finland and Sweden. They look the part, but Sweden is actually a mix of Gentle Giant, Big Guy and Huge Schoolgirl so he doesn't completely fits as Manly Man. Let's not forget that the Boisterous Bruiser of the duo is actually Finland, if we check the "Swedish/Polish wars" strip, and that Sweden actually likes sewing and is the one who takes active measures to adopt a child (re: Sealand, whom he "purchases" off the internet). The fun of the Sweden/Finland duo is seeing how the dynamics are played with among them.
Of the Italies, Lovino/South acts tougher than Feliciano/North but is just as sensitive.
Adding to the Romano-thing, Spain and him (respectively), although Romano just acts tough, and is actually a whiny little crybaby like his brother.
One of the oddest/funniest examples is the Poland/Lithuania duo. Liet fits the Sensitive Guy part nicely in looks and behavior, whereas Poland is outspoken, cheerful and stubborn like several Manly Men... and is also a Wholesome Crossdresser who talks like a Valley Girl.
Greece fits in both sides of the spectrum, acting as Manly Man to his good friend (and one-time lover) Japan and as Sensitive Guy to his much hated arch-rival Turkey.
Chika Akatsuki and Shito Tachibana from Zombie Loan, although they don't quite fit the standard definition...
Katekyo Hitman Reborn!: Tsuna is the sensitive guy to Gokudera's slightly more manly man, who also harbors considerable Ho Yay towards Tsuna.
There's also Yamamoto (sensitive) and Gokudera (manly).
The blood brothers Toki and Raoh from Fist of the North Star have this kind of relationship, with the former being a healer who treats the sick and the latter a tyrannical conqueror. Of course, Toki can kick as much ass as his brother Raoh, its just that he's more reserved about it and only does it when necessary.
Saiyuki: Goku is the sensitive guy to Gojyo's manly man, and the manly man to Hakkai's sensitive guy.
Played with in SWOT. Iwashida, the sensitive guy, is fairly typical since was the weakly kid who was always victimized by the delinquents in his school. He's also all about being loyal to his newfound friendships. The manly man is Manabizaki who is crass, arrogant, routinely beats up delinquents, and has a Hair-Trigger Temper. He's also a "swot," someone who studies way too much, and is initially dismissed as a harmless nerd,
Sakura Gari: Masataka (sensitive) to Souma (manly) are a Yaoi (and very twisted) version of this.
As well as Souma and Dr. Katsuragi. And Masataka actually is the Sensitive Guy to his older brother Takafumi, but the Manly Man (not by THAT much) to his younger brother Mitsugu. Respectively there's also Youya and Masataka.
Shun (sensitive) and either Hyoga, Ikki or Seiya (manly) from Saint Seiya.
Again, there are many partnerships/rivalries/brother duos that play with this concept to different degrees: Shun and Hyoga, Shiryu and Seiya, Seiya and Jabu, Aiolos and Aiolia, Asterion and Moses, Hyoga and Isaac, Kanon and Saga, Milo and Camus, Mu and Shiryu, Shiryu and Ohko, Aphrodite and Deathmask...
In the sequel of the former, Saint Seiya Omega, we have Shiryu's son Ryuho (sensitive) and Haruto or Kouga (manly).
Professor Go (sensitive guy) and Chujo (manly man) from Giant Robo. Professor Go is always getting overcome with emotion and crying, but Chujo keeps walking along as a stoic paragon of masculinity. Naturally the two are best friends.
Mikael and Raphael from Tenshi Ni Narumonmostly play it straight - visually, Mikael is of slight build, feminine looking and Raphael is more muscular and manly looking in comparison. In terms of personality though, they have lots of shades of their opposite spectrum - Mikael is mostly cold, stubborn and shows that he can be pretty aggressive and determined when the need arises, while Raphael has rather mellow and carefree attitude and shows lots of kindness towards not only Mikael, but also Noelle and Natsumi. That said, the last episode plays it straight again, though - in the climax scene, it shows that Mikael is totally dependable on his teacher and helpless without his help, while Raphael appears as a strict and unbending, leaving his student to clean up the mess his responsible for.
Death the Kid is the sensitive guy to Black*Star's manly man in Soul Eater. This is most easily noticeable in the episode where they go to find Excalibur together, and Kid winds up riding on Black*Star's back, so as to avoid the water on the floor. Oddly enough, this is the episode where they become friends.
Future GPX Cyber Formula has Hayato Kazami (sensitive guy) to both Naoki Shinjyo and Bleed Kaga's manly men, although Kaga is less muscular and more cheerful (in the first 2 series) than the standard manly man.
Hayato and Johji Ohtomo played the sensitive guys to Shinjyo's manly man. Interestingly, Ohtomo's more muscular than Hayato and Shinjyo.
For side characters, Gudelhian and Heinel and Bootsvorz and Osamu. Katagiri plays the sensitive guy to Shinjyo's manly man.
D.N.Angel: Daisuke (sensitive guy) to Satoshi or Dark or Saehara (manly men).
Both of the same-sex partners in Sekirei are this, with the Ashikabi as the Sensitive Guys to their Manly Man Sekirei.
Minato is gentle and deeply emotional, and looks up to Kagari as a "cool guy". Kagari is a chain-smoking Casanova and a Mysterious Protector, and remains the more traditionally masculine of the pair even after his unstable state results in him becoming a Gender Bender.
Mikogami and Mutsu are a villainous example, playing the trope completely straight. The former is The Dandy, and highly emotional while the later is a quiet, serious Master Swordsman.
In Yes! Pretty Cure 5, this is essentially the dynamic between Coco (sensitive) and Nuts (manly), although not as severe as it could be.
The superheroes Hawk and Dove (the originals) would qualify.
British Kid's comics usually work on the "schoolyard rivals" model. Dennis the Menace bullies Walter the Softy, Bully Beef is regularly outsmarted by Chips, Smudge refuses to be clean like Percival Prim, Tough Nut picks on Softy Centre etc. Which character the reader is supposed to root for varies from story to story, but it's often the tough kid, further perpetuating the stereotype.
Hawkman is this to himself. "Carter Hall is a man of culture who enjoys fine wine, yet Hawkman is a barbarian who you can only be happy is on your side" as described by the Atom once.
Power Ring and Deathstorm in Forever Evil. Power Ring is a huge coward that hides behind his Ring of Power while Deathstorm is a stoic that calms Power Ring when he gets scared.
Astérix and Obelix. Asterix is smaller and physically weaker, but has a hard-headed, mature and quite sneaky personality. He is a good swordsman, enjoys one-upping the Romans but doesn't mess with them outside of an actual need to, and is more flirtatious and in-control around women than Obelix. Obelix is larger and stronger, but is mostly written to show off his cute, innocent traits, with even his love of punching Romans coming from a place of genuine, childlike appreciation for how much fun it is rather than any sadism. He also has a sweet little dog that he's dedicated to, and tends to cry and fall in love easily.
Both boys are the sensitive foil to Achmed's manly man, however.
In Empath: The Luckiest Smurf, Tapper is the Oirish Sensitive Smurf bartender who likes talking to his customers and speaking to them about The Bible, dressing in a striped vest and tie, while Duncan McSmurf (the Captain Ersatz of Gutsy from The Smurfs films) is the Brave Scot Manly Smurf who wears a kilt, whose hobbies involve physical sports and knocking Smurfs on their tails, especially if they happen to call him Gutsy. Both Tapper and Duncan happen to be friends with each other, with Duncan serving as the superego in the Power Trio of himself, Hefty (ego) and Tuffy (id).
The Narrator and Tyler from Fight Club at first appear to be this to a certain extent, then we realize fairly soon that they are Not So Different in terms of their attitude toward society and life in general, and this is before we find out that Tyler is actually the narrator's split personality.
Played with in The Other Guys. At first it looks like Extreme Doormat Allen (Will Ferrell) is the sensitive one and cynical Terry who wants to be The Hero (Mark Wahlberg) is the manly one. But then again, Allen is the ladies man with anger management issues while Terry is the one who knows ballet and how to play the harp (which he insists he learned as a kid in order to make fun of the sensitive guys who actually liked that stuff).
Serge and François in Les Roseaux sauvages (Wild Reeds). Serge: he's good at math and bad at French, he's macho, good at sports, into girls, and he's a country lad who wants to work on his parents' farm. François: he's good at French and bad at math, he's quiet, he has a heart condition that means he can't play sports, he's into film and literature, his best friend's a girl, he introduces Serge to the Big City (Toulouse, in this case) and he's into guys. François falls in love with Serge, who cannot reciprocate.
Comes up in Trevor. Thirteen-year-old Trevor likes Diana Ross, musical theatre and writing in his diary. He falls in unrequited love with the star of the intermediate baseball team.
Charles Xavier and Erik Lehnsherr in X-Men: First Class, both in their physique as well as their philosophies and methods.
The Avengers gives us the Odd Friendship variant on this trope when introverted, tormented Bruce Banner and snarky show-off Tony Stark hit it off as soon as they meet.
Sense and Sensibility has shy, sweet Edward Ferrars and world-weary ex-soldier Colonel Brandon whose favourite hobby is "suffering quietly".
Also, in Emma there's Mr Knightley, the very organised authority figure who always speaks his mind (in a way that could potentially be misconstrued as rude) and Frank Churchill, who loves parties and dancing at balls.
Northanger Abbey has two brothers. The elder, Captain Tilney, is a soldier who likes 'sowing his wild oats,' whereas his younger brother Henry is a clergyman who likes reading novels.
To an extent, Crowley and Aziraphale from Good Omens fit this trope, although this might also be because they are a Demon and an Angel, respectively. It should also be noted that the reason they each like the other so much is because Crowley sees Aziraphale as being just enough of a bastard to like, and Aziraphale sees Crowley as just enough of a good person not to hate, much to both of their chagrin.
In Harry Potter, the brunette Sirius Black is witty, temperamental and loudmouthed (manly man), while the sandy-blond Remus Lupin is calm, quiet and collected (sensitive guy). Even their hair shows it.
In The Lord of the Rings Boromir and Faramir, sons of the Steward of Gondor, fit this trope to a "T": Boromir is a mighty warrior and military leader, interested in warfare and little else, Faramir loves poetry and lore (although he's also a soldier). In this case, the difference is mostly one of attitude- Boromir loves fighting and being a soldier for its own sake (though he's guided by a strong sense of honor and duty) while Faramir views soldiering as a service he must render for the good of his people even though he's a scholar by inclination.
And to a lesser extent, Sam seems to be tougher and has a bigger inclination towards violence than Frodo, but this might be due to the ferocity with which he protects him.
Njáll and Gunnar in Njáls Saga. Gunnar is the stereotyped Viking Boisterous Bruiser. Njáll is a wise sage, and a clever lawyer and interclan diplomat.
C.L. Moore's Northwest Smith and Yarol the Venusian provide an interesting variation on the trope. While Smith is a rugged, muscular space cowboy and Yarol is a delicate-looking young man who resembles a choirboy, the former occasionally displays flashes of sensitivity whereas the latter doesn't possess a shred of kindness or decency.
The Hardy Boys books use this for Frank and Joe. Frank is the more intellectual, cool-headed brother who likes art, literature, and strategy. Joe is the athletic hot-headed sports-fan who likes to charge in head first. While this only showed up in faint traces in earlier books, in more recent series, after a small bit of Flanderization, it's become much more prominent, with the boys actually arguing about which is the better tactic when in comes to solving a case.
In The Hunger Games Katniss begins to see potential loves interests in two guys, Peeta, the baker's son who decorates the cakes and Gale, her hunting partner. Gale is angry with the Capitol for making them participate in the games while Peeta is reflective on how he can maintain his identity in the games despite the Capitol using them.
Played with in Darkfall by Dean Koontz. Two supporting characters are introduced early on, the meek-looking, bowtie-wearing Nevetsky and the tough, mean-looking Blaine. Jack Dawson assumes Nevetsky is the Sensitive Guy and Blaine the Manly Man; in reality, the big and tough Blaine is the kind and gentle one while the less intimidating-looking Nevetsky is the loudmouthed, antagonistic brutish one.
Skylar and Rafael in Gives Light. Skylar is mellow and thoughtful while Rafael is quick to settle arguments with his fists. In a subversion, though, Rafael likes art, romance, and fairy tales, while Skylar likes baseball and slasher flicks.
Ian and Jared from The Host. This is also the relationship Ian has with his brother, Kyle.
In Horatio Hornblower, Hornblower and his Number Two, Bush, are this kind of pair. Hornblower is a broody, self-loathing mess when he's not being a brilliant naval captain and can't stop thinking about the prospect of death and mutilation in battle even if he never shirks from it. Bush is a stolid and stoicLightning Bruiser who's unfazed by hardship but also lacking in Hornblower's genius.
NCIS has McGee, who is more or less a Camp Straight, and Tony, who, hiding behind the Jerkass Façade, constantly derides him for it. Interestingly, McGee's 'soft side' tends to get him dates; Tony, more of a slick womanizer by nature, often sticks his foot into his mouth by making fun of McGee's feminine tendencies in front of sympathetic ladies. It's also played with in that, while Tony is a tough guy type, more physically capable and stereotypically masculine than McGee (he's a street-smart athlete to McGee's academia and noodle-arm), he's also a dedicated follower of fashion where McGee wore the same suit for his first four seasons. He makes fun of McGee for moisturising, but he spends $100 on a tie.
Home Improvement. Tim was a tool-loving manly-grunting man and Al was the sensitive and overly emotional type (though still very burly and masculine-looking). Being a real man was one of the show's main themes and Al's sissy-ness was the butt of many jokes but Al was shown to be much smarter than Tim. In addition, they were united as an Odd Couple by their mutual love of craftsmanship. Tim was also contrasted with his neighbor Wilson, an introspective Renaissance Man.
Parks and Recreation likes to contrast manly man Ron Swanson with overenthusiastic New Age health nut Chris Traeger.
In Firefly the greedy thug Jayne, is hostile toward the classy doctor Simon. Their contrasting personalities are best seen in Jaynestown where Jayne feel comfortable in the rough, poor world and Simon clings to being proper. Their rivalry is best seen in Ariel when Jayne demands that Simon be left on the core planet after being stabbed by Simon's sister. Mal then deals with Jayne's defensiveness and Simon's concern for his sister.
Supernatural appears to be a textbook version of this trope, but hard-drinking and -playing, gun-happy 'Manly Man' Dean is more often in a nurturing role than little brotherSam, and will unashamedly cry where his family's concerned. While Sam's more likely to cry even for strangers and prefers nonviolent paths, he becomes single-minded enough to forsake his characteristic empathy under the wrong circumstances. Whicharecommon.
Gunn and Wesley in season 2 of Angel are an example. Gunn was the hardened, street-born brawler who was a human able to go toe-to-toe with a vampire. Wesley was the more high-born scholar who hadn't quite outgrown British Stuffiness. It ceased to apply when Wes went all Darker and Edgier, developing Perma Stubble and a growly voice.
Doctor Cox (manly man) and JD in Scrubs. Also, to some extent, Turk and JD, though, while Turk is quite sensitive himself, he cannot compare to JD.
Marshall qualifies as the sensitive guy as well. This might be more of a Gentle Giant thing though.
ESPN's Mike and Mike in the Morning show uses this trope, with Mike Golic (a former NFL defensive lineman) as the manly man and Mike Greenberg as the Sensitive Guy. One of the features of their column in ESPN the Magazine is the "Manly/Metro tip", with Golic's "manly" tip accompanied by an icon of a beer mug and Greeny's "Metro" tip accompanied by an icon of a martini glass.
Noah (sensitive) and Wade (manly) from Noah's Arc. Also, to an extent Junito (sensitive) and Ricky (though Ricky's "manly" tends to be sexually aggressive and detached).
The titular brothers from Simon And Simon- The younger brother A.J. is the Sensitive Guy, whereas older brother Rick is the Manly Man.
The brothers Healy, Mark (macho) and David (sensitive), on Roseanne. If they were taking a side, it's hard to tell which one, becuase Mark was a testosterone-poisoned moron and David was a henpecked wuss.
Friends: Chandler (sensitive) and Joey (manly). Generally Joey will sleep with girls for a night and Chandler will make them breakfast the next morning.
Played with in one episode: Phoebe was dating two guys at the same time, a manly fireman and a sensitive teacher. She tries to break up with the fireman but discovers that's he's also sensitive and artistic to boot ("He has access to lots of charcoal"). He tries to break up with the teacher while he's fixing up his apartment, and he's totally hunky.
Also played with in Criminal Minds: From their first appearances, Morgan and Reid seem set up to be this trope (Morgan is playing a vaguely "educational" drinking game with a group of women, whereas Reid, the Genius Prodigy, is interrupting mentor/team leader Gideon's lecture on profiling and tailing him like a puppy). As the series goes on, though they both display examples of following the trope (e.g., Morgan is the team's designated door-kicker and likes portraying himself as either a ladies' man or strong enough to handle anything, while Reid prefers trying to talk unsubs down from confrontations, very visibly has trouble with some cases, is a James Bondage, and can barely talk to a woman outside of his mother or the context of work), and going against it (e.g., Reid takes cases personally hard, but has had to work at making himself more sympathetic and tactful toward victims and persons of interest, while Morgan often ends up in a nurturing role towards other team members, especially Garcia and Reid). One typically masculine trait both of them share? Although Reid's emotional responses to situations are more visible, more often than not, both are loath to talk about their feelings.
Oz has the yaoi couple Beecher (sensitive) and Keller (manly).
Used heavily in the last two seasons of The X-Files with Mulder and Doggett. Mulder was originally written (as was Scully) to invert traditional gender roles. He's a psychologist, intuitive, and emotional. When he gets abducted in season 8, John Doggett was brought in as Scully's partner. However, by this point Scully had lost a lot of her skepticism and become more Mulder-like. And since Chris Carter liked the X-Files partnerships to be opposites (and he didn't want the fans to see Doggett as replacing Mulder), Doggett is the skeptic in the partnership and Mulder's opposite. He was a cop and works off of hard facts. He thinks Mulder is crazy even before he meets him, and makes his opinion known to Scully openly. When Mulder returns near the end of season 8, the face-off begins. Mulder and Doggett cannot stand each other.
The Hardy Boys Nancy Drew Mysteries: Almost right down to a T: Frank Hardy, Manly (Parker Stevenson being the muscled prep-school jock into surfing). Younger Brother Joe, Sensitive (Shaun Cassidy, slender teen-idol musician). Interesting to note, this is the absolute opposite of the way things were in the books: usually Frank is the intellectual one more likely to enjoy art, and Joe is the more athletic jock. Though the show occasionally played with it by having Frank shove Joe out front in dangerous situations:
(as the brothers are about to step into a crypt containing god-knows-what)
Joe: Well...you're the oldest.
Frank: Yeah, but you're more agile on your feet, and stronger.
Joe: Since when?
Frank: Since right now.
Jack is Manly and Ianto is Sensitive in Torchwood.
The elegant and aristocratic Fulgrim and the burly, short-tempered Ferrus Manus from Warhammer 40,000 had one of the closest relationships in a family of 18 brothers. Until, literally, all hell breaks loose and civil war breaks out with the Horus Heresy, and Fulgrim gleefully kills Ferrus. Fulgrim still doesn't take it well, in the end.
Robin and Lancelot in Spamalot. Slightly subverted in that Lancelot turns out to be gay.
Though the subversion here is not of the trope, but of the stereotype that gay men are less manly. Even after his coming out song, Lancelot is a manlier character than Robin.
In Mozart's The Magic Flute, Tamino and Papageno tend to come across this way, though how much depends on the production. Ironically, Tamino, the Manly Man (even though he faints at the sight of a big snake), is a light tenor role, while Papageno, the Sensitive Guy, is a baritone.
Miles Edgeworth and Dick Gumshoe from the Ace Attorney series. For further contrast Gumshoe is an extremely incompetent detective compared to the highly competent prosecutor Edgeworth.
They somewhat subvert this trope, in terms of personality. Gumshoe, while being the biggest character in the series, is actually a nice guy deep down. Miles, on the other hand, isn't above physical abuse to straighten up Gumshoe, despite being half of Dick's size.
Mario and Luigi, to some extent. Mario has a quick-to-act get-up-and-go fearless attitude, while Luigi has a hesitant, cautious, and timid demeanor. "Mario" even means "manly".
Solid Snake (manly man) and Otacon (sensitive guy) from Metal Gear Solid are made of this trope, although Snake's more philosophical and Otacon's sexual history is significantly more important to the plot than Snake's. And both are as emotionally needy as each other, although they show it in different ways.
Azel/Lex, Cuan/Sigurd, and Seliph/Lewyn in the fourth game;
Fin/Glade, Salem/Pirn, and Pirn/Lifis in the fifth;
Wolt/Roy, Wade/Lott, Lugh/either Ray or Chad, and Allen/Lance in the sixth;
Kent/Sain, Raven/Lucius, Lowen/Harken and Hector/Eliwood in the seventh;
Artur/either Joshua or Cormag, Seth/either Garcia or Cormag, Lyon/Ephraim, Knoll/Duessel and Saleh/Gerik in the eighth
Ike and Soren from the ninth and tenth sort of play around with who is which. Ike is the muscular Badass while Soren is the Squishy Wizard, but Ike is also much more empathetic and kind while Soren is very harsh and judgmental.
In Fire Emblem Awakening, there's Prince Chrom and his childhood rival Vaike. Similarly, Ricken and Henry. The second generation gives us Brady and Owain, and maybe Laurent and Gerome.
Geo Stelar (sensitive guy) and Omega-Xis (Manly Man) in Mega Man Star Force. In such an awkward way.
Parodied in Grand Theft Auto IV with the television show "The Men's Room With Bas And Jeremy", Jeremy St. Ives being an effeminite pacifist who's main advice usually revolves around "rectal marital issues" and "colon cleansing", and former ultimate fighter Bas Rutten (as he is portrayedin this game) being a hyper-masculine, borderline Ax-Crazy who's every sentence eventually devolves into violence sprinkled with gore.
Legacy of Kain: Brusque warlord Kain is a Manly Man while thoughtful, angsty Raziel is a Sensitive Guy. This trope can also apply to Manly Man Vorador (callous, violent, has a harem) and his sire Sensitive Guy Janos Audron (kind, understanding, hermetic).
Also, slightly subverted in the case of Refia and Desch; Desch is a manly cold guy, and Refia is the sensitive chick. Although Refia tends to have a more impulsive and brash attitude than Desch at times.
Fallout: New Vegas and All Roads in particular casts Benny and Swank like this. Benny is scheming to take on Vegas, Swank is worried about the extremes he'll go to... and about him getting cigarette burns on the carpets.
The Dynasty Warriors series has three sets of this. Bodyguards Dian Wei (Manly) and Xu Zhu (Sensitive) and (As of DW6) generals Xiahou Yuan (Manly) and Zhang He (Sensitive) of Wei, and Sworn Brothers Sun Ce (Manly) and Zhou Yu (Sensitive) of Wu.
Would the relationship between Strong Bad and Strong Sad count? It's more antagonistic though, with Strong Bad making Strong Sad's life as miserable as possible. But there are instances of them getting along.
Orville (Sensitive) and Roy (Manly): Orville is a quiet, well-mannered squirrel who dreams of flying while Roy is a mischievious prankster raccoon.
Matt (Sensitive) and Ricky (Manly): Matt is a hopless romantic who constantly picks flowers while Ricky is basically an Expy of Roy from the original Orville comic.
Steve Roberts (sensitive) and Gavin Taylore (manly) in KateModern, particularly season 2.
The short-lived Fan Fiction archive Fanlib failed after leading a particularly offensive and ill-advised marketing campaign starring "Pink Guy" and "Blue Guy." After apparently mistaking its primarily queer female audience for heterosexual teenage boys, "Pink Guy" and "Blue Guy" appeared in an ad promoting Fanlib as manly and powerful/attractive and non-Fanlib as feminine and weak/unattractive.
The Nostalgia Critic and The Other Guy (Doug and Rob Walker) seem to go for this trope, with Critic being quite girly and The Other Guy much more in control. Or it could be that Doug is the younger brother who is very often either being moe or a total limelight-loving flirt while Rob stays in the background.
A twofer in Demo Reel with Donnie DuPre and Carl Copenhagan, and Tacoma Narrows and Quinn. Donnie was a Cuddle Bug queerball who had no complaints with wearing eyeliner and lipstick, while Carl used to work with The Stasi and thought everything could be solved by shooting at it. Tacoma was a Nice Guy whose voice gets mistaken for his mother's sister, plus he was delighted to hear that he didn't look bad in a dress, while Quinn was a purely Irish Good Is Not NiceBlood Knight.
Ian and Anthony of Smosh. Ian (sensitive) is slightly more emotional, gets insulted more easily, and has even cried on camera for real. Anthony (manly) is the more vitriolic friend, makes fun of Ian more than Ian makes fun of him, and has never really shown a sensitive side, although his girlfriend claims he DOES have one.
Inverted AND Played for Laughs when they both flip their respective personalities, with Pat being the Wuss and Matt being the tough guy when they play Slender and its sequel.
Monster High's Jekell and Hyde rutine is done like this, with Jackson being some tipical soft-spoken nerd with a dislike to loud music, and Holt being the loud-mouthed disc jockey with flaiming red hair.
Interestingly enough, Sokka switches roles depending on who he's partnered up with. He is manly in comparison to the happy and playful Aang, but sensitive compared with the emotionally-repressed Zuko. But all good male characters in Avatar: The Last Airbender show a sensitive side to some degree.
Zapp Brannigan and Kif Kroker from Futurama. Zapp is a classic Ted Baxter Captain, and sees himself as a manly courageous stud. Kif on the other hand starts out as a weary Deadpan Snarker but grows more into the Sensitive Guy mold through his relationship with Amy.
The titular Tick as the manly man and his sidekick, Arthur, as the sensitive guy.
Buck Tuddrussell (macho) and the Larry 3000 (sensitive) on Time Squad — in the first seven episodes of season one, at least. From the episode "Larry Upgrade" to the series finale ("Orphan Substitute"), the pairing went from "Macho Man and Sensitive Guy hanging out with an orphaned eight-year-old history buff" into Larry and Buck acting like a married couple/foster parents to Otto. It doesn't help matters that the Larry 3000 comes off as Ambiguously Gay at best and Camp Gay at worst.
There was also Lewis and Clark, with just as much Ho Yay as Tudrussell and Larry.
The Ren & Stimpy Show: Stimpy is the sensitive guy to Ren's manly man (which was made more obvious in the Adult Party Cartoon run of R&S).
Rugrats: Chuckie is the sensitive guy to Tommy's manly man.
Recess: Mikey and Gus (sensitive) and T.J. and Vince (manly)
South Park: This trope is primarily played with the naive and idealistic Butters to the sadistic and aggressive Cartman.
Adding on to this, the main characters generally form two pairs for who is sensitive and manly respectively. Stan is an animal lover and usually prefers making peace rather than fighting while Kyle holds the highest morals in the group and is generally the most compassionate of his friends (although, he has one hell of a temper) (Sensitive Guys). On the other hand, Cartman (despite his fondness for tea parties) is forceful, aggressive, and sadistic as mentioned above while Kenny is primarily interested in sex and drugs and perhaps has been seen crying the least among his friends (Manly Men). Butters tends to be the Sensitive Guy to the rest of the main characters in general.