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Makeup has existed for a very long time, to hide imperfections, but also for ritual and religious purposes. In Ancient Egypt, both high-class men and women would wear eyeliner and nail polish to protect themselves against curses (and flies and the glare of the Sun). And in the court of Versailles both everyone was in thick layers of make-up and perfume (mostly to hide the smell).
Nowadays, makeup is considered a mostly feminine thing to wear, and most men wear it for religious purposes, or if they're on stage.
In fiction, makeup is either an indication of religious figures, insane psychopathic clowns or people with generally a bolt loose, the more emo-tastic brand of Bad Boys, and general mysterious dudes. It also acts as Fetish Fuel; just ask any fan of Jack Sparrow.
So yeah, makeup on dudes in a context other than Crossdresser, Camp Gay or Paper-Thin Disguise. Leaves one prone to Your Makeup Is Running. See also Excessive Evil Eyeshadow and Real Men Wear Pink.
Examples
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Anime & Manga
- A notable subversion is Gaara. It looks as though he has copious amounts of eye makeup (probably in keeping with his Goth style), but it is actually the result of chronic insomnia.
- More likely it's a mark showing he's a Jinchuuriki, like Naruto's "whiskers". Which would make more sense, considering Gaara still has the rings, despite having the Shukaku removed.
- Bookman in D. Gray-Man has two massive black facepaint circles around his eyes, leading his protege and future successor Lavi to call him a panda (which he hates.)
- Kamisama Kiss gives us two. Kurama may be wearing it since he performs onstage as an idol, but Tomoe? Perhaps guyliner is just standard issue to all bishounen demons...
- L from Death Note looks like he has this, but doesn't.
- Maybe they're actually circles you get from a lack of sleep.
Fan Fiction
- Draco Malfoy in My Immortal. (AN: A lot fo kewl boiz wer it ok!).
Film — Animated
- In Aladdin, Jafar seems to be wearing eyeliner.
Film — Live-Action
- Pretty much every Silent Movie star ever. This was partially because of the demands of the format, but also because the shadowy-eyed gent was the male ideal at the time. In the 20s, plenty of young men would don guyliner in order to look like Rudolph Valentino or Conrad Veidt.
- Xerxes in 300.
- Captain Jack Sparrow in Pirates of the Caribbean. It's actually to reflect sunlight.
- Blackbeard and Jack's father also wear black kohl, but not as thickly as Jack.
- Robert Downey Jr. in Iron Man, whenever it shows him in the suit talking with the AI. Because so much of the film is an extreme close-up on his face, the director wanted it to be well outlined.
- One of the Sheikh's men in Taken wears this, and he puts up a surprisingly valiant fight against Bryan, even managing to wound him, before he gets taken out.
- Peter O'Toole sports it as El-Auruns. What do you expect from a movie about an Ambiguously Gay Badass in an Arabian setting?
- Jareth in Labyrinth.
- Alex in A Clockwork Orange wears false eyelashes on one eye when with his droogs.
- At the goth-style wedding in 27 Dresses, the groom is wearing eyeliner.
- Unintentional: Stage actor Laurence Olivier insisted on wearing the kind of heavy makeup that emphasizes the actor's features so they can be seen from the back of the theater, even when he was in a movie — this looks odd in a close-up.
Literature
- The mooks in The Jennifer Morgue are forced to wear eyeliner by their boss, as it's a necessary component for his magical surveillance system. They are less than enthused, hiding it with Sunglasses at Night because, as one mook puts it, "Cosmetics don't go with G.I. Joe."
- The Hunger Games: Cinna, Katniss' personal stylist, always wears gold eyeliner.
- The world of A Brother's Price features inversions of almost every gender role and has Masculine Girl, Feminine Boy as the default, but that's almost. Even at court, Jerin is not put in makeup other than penciled chalk under his nails. When makeup does come up in the story, it's worn by women - specifically whores, women who sometimes dress as men to attract other women. They wear lip paint to draw attention to their mouths and suggest that they know how to use them. Jerin ends up disguised as a whore, and his companion has to apply the makeup herself.
Live-Action TV
Music
- Visual Kei
- Musical comedian Tim Minchin wears eyeliner to emphasize his face, because when he plays the piano he can't gesture with his hands and can show emotion only with his face.
- Often featured on the members of emo bands such as My Chemical Romance, AFI, The Used, and Fall Out Boy (and that includes their emo-pop followers).
- Green Day frontman Billie Joe Armstrong has had a similar aesthetic since the video for "Longview" off of Dookie and in subsequent works.
- David Bowie may be the only man who could rock the guyliner both in his 20s
 ◊ and his 50s.◊
- Tuomas Holopainen of Nightwish, leading to jokes that the real reason Tarja left was him stealing her makeup.
- Michael Stipe. Kind of invented this.
- Ville Valo of HIM as featured in the trope picture.
- Dero Goi, lead singer, drummer, and a keyboarder of the German goth metal group Oomph! often wears this. And he wears it very well.
- Thirty Seconds To Mars, back in the days of their second album, A Beautiful Lie.
- Josh Ramsay of Marianas Trench. One of the best examples is the music video for the song "Good To You."
- Robert Smith, frontman of The Cure.
- Gary Numan. In an interview, he mentioned an incident prior to a performance early in his career, where the makeup artist had applied so much foundation to cover up his problem skin that his eyes looked like the proverbial "pissholes in the snow". To rectify this, they added plenty of black eyeliner, and his trademark look was born.
- Baekhyun of Exo is famous for this.
Professional Wrestling
Video Games
- Cecil of Final Fantasy IV seems to be wearing black lipstick.
- That said, a lot of Amano's male designs wear make-up.
- Firion appears to wear it quite thickly, given his middle-eastern style look. Particularly prevalent in Dissidia.
- Axel of Kingdom Hearts has little tattoos under his eyes, and seems to be wearing eyeliner.
- In the Devil Summoner: Raidou Kuzunoha novel, the narration mentions that Raidou looks as if he's wearing eyeliner and lipstick, though it doesn't say that he actually is.
- The Sims 2 will allow you to put this on your male Sims if you wish.
- Wolf O'Donnell in the Star Fox series.
- Vossler in Final Fantasy XII seems to be wearing pretty heavy kohl. Of course, this makes sense since the man lives in a desert and dark around the eyes is a good way to prevent glare. Or like Richard Alpert he could just have dark eyelashes. Particularly noticeable in this scene at 1:39.
- Demon Lord Ghirahim of The Legend of Zelda: Skyward Sword.
Web Original
Western Animation
- On Gravity Falls, Robbie is not wearing make-up in his band's poster, he's wearing "eye paint for men."
Real Life
- Male actors in theater do this all the time.
- Adam Lambert was known during American Idol just as much for his guyliner◊ as his singing.
- Nestor Carbonell is often believed to be wearing eyeliner, but his eyelashes are just that dark.
- An Islamic convention called "Sunnah" features men applying paint around the eyes (known as "kohl"). Since sunnah means "things the Prophet did habitually", it's probable that this originates with its use as eye protection, and it makes sense in much if not most of the Muslim world. This is why so many Arabic characters in movies appear to be wearing eye make up. Also has the added effect of making Muslim villains look more sinister.
- Johnny Depp, and it looks awesome.
- For a short while, Ma'a Nonu of the All Blacks rugby team wore mascara.
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