Store Clerk: Something that says... leatherdaddy?
Tobias: Oh, is there such a thing?
The LGBT community has a variety of subcultures and groups. One component has historical roots in the BDSM community and to biker culture, resulting in a noticeable number of gay men wearing a LOT of cured animal hide in suggestive cuts.
The leather tradition is generally traced back to gay servicemen returning from World War II. They became the biker gangs of The '50s, and the subculture grew from there. The BDSM part sort of merged in later, though it's not a bonafide requirement that a leatherman be into kink. In fact, some of the older leathermen (the "old guard") have few, if any, BDSM tendencies. Just a strict code of honor, obedience to tradition and hierarchy and a strict set of rules.
A related but distinct group are bears, masculine types with body hair, heavy-set builds, and/or "traditionally" masculine behaviour. There is a lot of overlap between the two groups, but the same way not all leathermen are into BDSM, not all bears are into leather. Both groups formed in part because the gay community itself had developed certain stereotypical expectations — typically, hairless young "metrosexuals". Or drag queens.
The defining characteristic of both groups was a certain visibly identifiable look and behavior. Which, of course, meant that once TV got around to even acknowledging that there was a gay subculture, these two were mashed together as possibly the stereotype to portray, after "classical" gay archetypes. Especially if the setting involved jail at any point. The popularity of The Village People and the artwork of Tom of Finland probably helped.
Needless to say, character development seldom proceeds beyond "big, hairy, aggressive gay biker".
It isn't really clear why this archetype never spread to the fantasies of straight women, even though there's nothing inherently gay about it aside from the stigmas attached to it.
- One of the last episodes of Dragon Ball Z has a World Tournament challenger named Otokosuki (Japanese for boy-love) who seems to take a liking to Trunks. He doesn't wear a jacket, but otherwise fits the archetype.
- Dante in the Fist of the North Star anime looks nearly exactly like the picture, just tint his hair blue and make the mustache bristle-ier. He also kisses his victims full on the mouth.
- Mello from Death Note. He is a much more Bishounen example of this trope than the standard (to the point of frequently being mistaken for a girl by first-time manga readers).
- The artwork of Tom of Finland.
- Leatherboy was a rather notable version of this when he tried out for the Marvel Universe team Great Lakes Avengers. Turns out he wasn't the gay member.
- The Midnighter from The Authority embodies this trope. He's also an Alternate Company Equivalent of Batman, only with the Ho Yay between him and the Superman-Expy as canon rather than subtext.
- X-Factor's and formerly X-Force's Shatterstar wears primarily white leather outfits with some suggestive seam placement.
- Several appear in the Ms. Tree story "Skeleton in the Closet", attempting to rough up Mike, Jr. after he is exposed as a homophobe.
- David from the Furry Comic Associated Student Bodies, the resident macho type. In one story, he takes the protagonist Daniel to the local leather bar, dressed in full leatherman attire himself. Daniel's reaction to the outfit:
Daniel: I look like a Village People. [sic]
David: My favorite! Music with meaning!
- Marshal Law is straight, but several characters assume he is gay because he dresses like this.
- The denizens of the Blue Oyster Bar in the Police Academy movie franchise.
- In Serial (1980), Christopher Lee plays a man who is a scary gay biker at the weekend and a highly respectable 'suit' the rest of the time.
- Australian actor Vernon Wells is best known for playing this type of character: Wez in The Road Warrior and Cpt. Bennett in Commando are probably the best known.
- In Cruising (1980), Al Pacino plays a rookie cop who must go undercover in the New York leather scene in order to catch a serial killer.
- In A Nightmare on Elm Street Part 2: Freddy's Revenge, Coach Schneider is revealed to be one when Jesse encounters him at the underground club.
- The Mad Max franchise's aesthetic, and the trope it codified, owes a lot of inspiration to this trope mixed with Scavenged Punk.
- This is one of the many, many gay stereotypes unintentionally evoked by Tobias on Arrested Development. See the above quote. He even joined a barber shop quartet of leathermen.
- Matthew from NewsRadio once dressed up as what he insists was a "motorcycle enthusiast" for Halloween. In fact, the words "Butch Biker" was written in rhinestone on the back of his jacket just so people wouldn't be confused. It didn't work and he couldn't understand why.
- Trey from Noah's Arc posed as one of these for a calendar shoot.
- Vito was seen by some low-ranking soldiers attending a gay bar in one of these outfits on The Sopranos episode "Mr and Mrs Sacrimoni Request", which sealed his fate.
- There was a short-lived Saturday Night Live recurring sketch called "Leatherman" about a man (played by Jimmy Fallon) who owns a leather clothing store.
- Referenced in a Mr. Show sketch in which a heavy metal band plays Fire Island to a packed crowd of leathermen.
- The Ben Stiller Show features a Beverly Hills, 90210 parody sketch in which one of the high school students dresses and acts, rather inexplicably, like a leatherman. He's played by Bob Odenkirk.
- The main stereotype played with by Razor Ramon "Hard Gay" (though his outfit is more PVC than leather).
- In their early days, the Blue Öyster Cult tended to the leather look. (Check out the inner sleeve photos on On Your Feet - Or On Your Knees.) They had a substantial following garnered from two New York groups - gays and bikers. A stage looknote that appealed to both was a no-brainer. Bass player Joey Bouchard recalls they got their stage leather from a BDSM boutique specialising in gay bondage. The gay bar in the Police Academy series is called The Blue Oyster and could well be Homage to this...
- Glenn Hughes (important note: not the one from Deep Purple and Black Sabbath, who is a different guy with the same name) provides the page image. He was an actual motorcycle enthusiast even before joining The Village People.
- Rob Halford's fondness for Leatherman costumes while on stage with Judas Priest somewhat lessened the surprise when he came out.
- Hell, all five members are usually dressed to the nines in leather (look at The Essential Judas Priest album).
- Rob Halford made leatherman/BDSM getups an integral part of metal fashion, unbeknownst to the (largely straight) metal bands that spread like wildfire during The '80s.
- Then again, Rob Halford's sexuality was pretty obvious when "Turbo Lover" was released.
- Speaking of songs: "Hell Bent For Leather" from as early as 1978.
- Rob Halford plays the leader of the fire barons (essentially wearing his old outfit) in Brütal Legend. Interestingly, he also plays a preening Hair Metal singer, and the fire barons hate him.
- Referenced in the song "Real Men" by Joe Jackson:
"All the gays are macho/ Can't you see the leather shine?"
- X Japan, especially 87-92 for almost everyone at one point or another, but the ones that really took the trope and ran with it were Toshi and Taiji.
- Freddie Mercury of Queen.
- Adam Lambert, the openly gay, eighth season runner-up of American Idol. He even sports a leather jacket on the cover of his album Tresspassing.
- Lou Reed's look on the front cover of Transformer is pure Leatherman.
- Shadowrun canonically has an entire motorcycle gang of leathermen in Seattle. The Leather Devils draw on the long tradition of gay motorcycle clubs but have also veered into outlaw motorcycle club activities, mainly with a tilt towards vandalism, blackmail, prostitution, and porn production. And yes, they're all men.
- Angels in America features a scene in which Louis has sex with a random leatherman in Central Park. The character is aptly named "(leather)man in the park", and is supposed to be played by the actor who plays Louis' ex-lover Prior.
- Michel Tremblay's Hosanna depicts a relationship between a Drag Queen (the title character) and a Leatherman biker named Cuirette.
- Wolf O'Donnell in Star Fox and Super Smash Bros. is increasingly this with each new outfit, providing a (possibly) heterosexual example.
- Hsu Hao in Mortal Kombat.
- Paul Phoenix from Tekken is a heterosexual example, having worn plenty of studded leather outfits across the series.
- Flak the weapons dealer in Fallout 3. The player character in Fallout 3 and New Vegas, can be this if they like (and are male); a lot of raider armor in particular is suited to it. And then there's the Confirmed Bachelor perk, which gives you some rather suggestive dialog choices with men.
- Ash from the third edition of Streets of Rage. Only in the Japanese version, though.
- Aqua Regia has Daniel, wearing a leather jacket, biker gloves, combat boots, tight leather chaps in some images, with black jeans beneath. Like Paul Phoenix, it's also a heterosexual example.
- Blur the Lines has quite a few, including a BSDM leather daddy and a biker.
- The cast of Manly Guys Doing Manly Things includes Max, who ironically enough turns out to be totally straight and extremely weirded out by the fact Commander Badass and his fellow Manly Guys are more open to the idea.
- Mr. Slave on South Park.
- Meatwad from Aqua Teen Hunger Force became this temporarily. Ironically, in an attempt to prove his heterosexuality when Shake accused him of bisexuality.
- The General from Ronal the Barbarian, complete with a chain between his pierced nipples and bare buttocks to whip himself.
- One episode of The Cleveland Show had Roberta give Junior a makeover that got him mistaken for a lesbian. After the plot has concluded, Junior remarks that the next time he gets a makeover, there should be no doubt that he's a man who likes the ladies. Cut to Junior entering the house dressed like Glenn Hughes. "Why do I listen to you?!?"