Guyliner

Make up 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 eye-liner and nail-polish to protect themselves against curses. And in the court of Versailles both everyone was in thick layers of make-up and perfume (mostly to hide the smell).

Nowadays, make-up is considered a mostly feminine thing to wear, and most men wear it for religious purposes. In fiction, make-up 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, make-up on dudes in a context other than Cross Dresser, Camp Gay or Paper Thin Disguise. Leaves one prone to Your Makeup Is Running. See also Excessive Evil Eyeshadow and Real Men Wear Pink.

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
 * 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.)

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

 * Xerxes in Three Hundred.
 * 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 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.

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."

Live-Action TV
""Kelso. Your mascara's running.""
 * 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".


 * 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.
 * 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:
 * Lead singer Joo Byung Hee of the ficticious band Eye Candy in Shut Up Flower Boy Band. It's also Lampshaded because the actor, Lee Min Ki, is also a singer.
 * Min Tae Yeon in Vampire Prosecutor, who investigates homicides in Seoul.

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" boy bands such as Fall Out Boy and their followers and My Chemical Romance.
 * Green Day is hardly emo (though a few individual songs of theirs might count, but that's beside the point), but they've had a similar aesthetic since around the release of American Idiot, guyliner included.
 * Actually, Billie wears it in the video for "Longview" off of Dookie.
 * 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, though while Tomo has indulged in the past, special mention goes to Shannon Leto for his loyalty to eyeliner.
 * Josh Ramsay of Marianas Trench. One of the best examples is the music video for the song "Good To You."
 * No mentions of Robert Smith? Shame on you TV Tropes!

Professional Wrestling

 * The Undertaker wears eyeliner on a regular basis.

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

 * 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.
 * And the fangirls will never forget it.
 * Prince Jazan from Neopets wears guyliner, since he's from a Fantasy Counterpart Culture to Egypt.
 * One of the prizes given out for The Faeries' Ruin Plot is Jazan's Guyliner, a marking-type wearable by your Neopet.
 * In Thalias Musings, Thalia magically puts gold eyeliner on Apollo as a prank. He decides he likes it and leaves it on.

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"). 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.