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 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 men only wear it for cultural reasons, as a fashion statement, or if they're on stage. In fiction, makeup is either an indication of religious figures, insane psychopathic clowns or people with a screw loose, the more emo-tastic brand of Bad Boys, and generally 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.
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Anime & Manga
- Cedre from Toriko wears eyeshadow and seemingly a lot of eyeliner, specially under his eyes.
- 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 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. They're actually dark circles from lack of sleep.
- Judar of Magi ľ Labyrinth of Magic wears thick kohl, probably as an indication that he's up to no good. Then again, the series is based on the Arabian Nights.
- In InuYasha, many males, especially the villains, have extremely long hair and/or lipstick.
- Malik from Yu-Gi-Oh! eyeliner which extends into little angular pointy bits under his eyes. In his case, it's some kind of Egyptian thing. Duke/Otogi has similarly elaborate eyeliner, with a line halfway down his cheek on one side, which may have something to do with the fact his dad is a clown and he runs a clown-themed game shop.
- Pariah in Crisis on Infinite Earths looks like he has used too much guyliner on his eyes, which in his origin story appears after he accidentally destroyed his parallel universe.
- Draco Malfoy in My Immortal. (AN: A lot fo kewl boiz wer it ok!).
Film — Animated
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.
- Rodrick whenever he's playing with his band or partying in Diary of a Wimpy Kid. He even asks his mom for some on a short-notice gig.
- 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 Twenty Seven 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.
- Cinna in Catching Fire, as in the book. Contrasted with the bizarre get-ups everyone else in the Capitol wears, he actually looks quite understated, but at the same time a little unusual, which was the intended effect.
- Channing Tatum's character Caine in Jupiter Ascending.
- All movie incarnations of Batman use dark eyeshadow to extend the black mask (though at least once it leads to a blooper, as before the Dramatic Unmask in Batman Returns the makeup disappears).
- The film version of Winter Soldier replaces the Domino Mask with black eye shadow (when they're not Scary Shiny Glasses).
- Likewise, after Anakin Skywalker becomes Darth Vader in Revenge of the Sith but before he puts on the suit, he goes with this look to accent his bright red-and-yellow eyes. He's still got deep, shadowed eyes when the helmet comes off in Return of the Jedi, though that falls more under Creepy Shadowed Undereyes.
- 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.
- Sinbad presumably uses this for eye protection.
- Nestor Carbonell's character, Richard Alpert, on Lost was given the name "Guyliner" before it was officially mentioned. This is actually a subversion, as Nestor Carbonell just naturally looks like he's wearing makeup at all times- Word of God states that no makeup was actually applied. This did not stop Sawyer from giving him an eyeliner-related nickname.
- According to a special feature on the Season 5 DVD, they actually apply concealer to make his eyelashes lighter.
- The comedy series Hyperdrive features a (male) character who likes to wear "mank-up", which includes such products as "guyshadow" and "guyliner".
- On That '70s Show, Jackie puts makeup on Kelso to give him the "androgynous David Bowie look".
"Kelso. Your mascara's running."
- The Guy of Gisbornes's got guyliner in the BBC series.
- Samuel on Heroes - again, eyeliner.
- In the Star Trek episode "The Enemy Within", the evil Kirk is given eyeliner to make him look more EVIL!!! Later, he applies makeup to his face to hide scratches on his face that distinguish him from the good Kirk.
- The Hatter (Andrew Lee Potts) in Alice.
- David Tennant gamely put some on for a Catherine Tate Christmas special as a Camp Gay Ghost of Christmas Present. And the fangirls rejoiced.
- Eliot of Leverage uses this (and a rather fruity scarf) to blend in at a fashion show. Hardison, predictably, gives him a hard time about it.
- The Addams Family. Gomez rocks it, though it isn't commented on in-series.
- Generation Kill: Seriously, Captain Patterson either has the most luxurious eyelashes ever seen on a man, or he's wearing eyeliner. It's probably not eyeliner. But WOW.
- Kamen Rider OOO: Ankh, in his "possessing Hina's brother" form. He looks so Bishonen that his deep voice is really weird...
- Joel Mchale would wear eyeliner whenever he was paroding Bruno from the Novela La Madrastra.
- In Game of Thrones Khal Drogo wears makeup to darken the area around his eyes, similar to kohl. It's apparently acceptable for men in his culture, though no other Dothraki are seen wearing it. At any rate, questioning the masculinity of the undefeated leader of a Barbarian Tribe would probably be unwise.
- Gendry appears to be wearing it in the second series.
- The Criss Angel Expy in the Supernatural episode "Criss Angel Is a Douchebag". This is commented on by the aging magicians, all wearing suits.
- Guyliner is very prevalent in Asian entertainment, especially Korean Series and K Pop. Notable TV Live Action:
- Floki in Vikings.
- Being an Expy of Jack Sparrow from Pirates of the Caribbean, Hook rocks some guyliner.
- Teal'c, in the first several seasons of Stargate SG-1. This vanished around the same time as he let his hair grow out.
- Anthony Ainley's version of the Master from Doctor Who usually had a bit of eyeliner, which shows up better when he gets a close-up. The fandom is delighted by this.
- 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.
- System of a Down's guitarist, songwriter and occasional vocalist Daron Malakian regularly wears eyeliner when performing on stage and when posing for photos.
- Often featured on the members of emo bands such as My Chemical Romance, AFI, The Used, and Fall Out Boy (and their followers)...at least until they lost interest, which hasn't really stopped non-fans and fans alike from still strongly associating guyliner with them long after they've stopped using it heavily.
- Green Day frontman Billie Joe Armstrong has had a similar aesthetic since the video for "Longview" off of Dookie and in subsequent works.
- Marilyn Manson wears guyliner.
- 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.
- 30 Seconds to Mars, back in the days of their second album, A Beautiful Lie. Despite frontman Jared Leto being more commonly associated with it, the drummer (and his brother) Shannon actually wore it the most out of everyone.
- 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.
- Voltaire does this often. It works for him incredibly well.
- Lou Reed on the cover of Transformer.
- Brian Eno when he was with Roxy Music.
- Danny Elfman in his Oingo Boingo days.
- 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: Final Fantasy.
- 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.
- Final Fantasy XIV allows this as a choice during character creation.
- 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 and 3 will allow you to put this on your male Sims if you wish.
- Wolf O'Donnell in the Star Fox series.
- Demon Lord Ghirahim of The Legend of Zelda: Skyward Sword.
- In Lollipop Chainsaw, Juliet actually calls the Punk Rock Zombie, Zed, this. "That makes Guyliner here like the most uncoolest guy ever!"
- The improved graphics in later games have revealed that Diabolical Mastermind Matsunaga Hisahide from Sengoku Basara wears ominous (yet extremely stylish) cat-eye liner.
- Pagan Min of Far Cry 4 wears eyeliner, being a very flamboyant tinpot dictator.
- Doug Walker wore a lot of eyeliner to do his Melvin, Brother of the Joker skit. Right after he filmed the the "Top 11 Dumbest Superman Movie moments" episode of The Nostalgia Critic and he didn't take it completely out.
- Prince Jazan from Neopets wears guyliner, since he's from a Fantasy Counterpart Culture to Egypt. Amusingly, one of the prizes given out for The Faeries' Ruin Plot is Jazan's Guyliner, a marking-type wearable for your Neopet.
- In Thalia's Musings, Thalia magically puts gold eyeliner on Apollo as a prank. He decides he likes it and leaves it on.
- The Cine-Masochist wears it on three occasions. Once as "Todd Haynes' in Infamous Sphere's review of glam movie Velvet Goldmine, once for the whole duration of his review of Keoma, and finally as his performance as "Random Naked Serbian Indian".
- In episode "A New Age of Aluminium" from The Autobiography of Jane Eyre, Warren Danton and Mr Rochester both wear eye liner because the party (Thornfield Exports Visual Art Festival, a rebranding event) has circus for its theme. Mr Rochester is dressed up as a clown. Warren points out that ladies find Guyliners very attractive, though he migh be snarking. Here is a link.
- In Noob, Judge Dead's real life style could be used for the Emo Teen page, guy liner is both mentioned in his novel description and seen in his webseries appearances. The latter also includes it on his old gaming avatar and his current In the Hood one.
- 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.