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- Faye Valentine from Cowboy Bebop. She's a Femme Fatale and a Broken Bird who's just looking for love... and for that big gambling win (she's compared to the Queen of Hearts, for obvious reasons). In this case, it's justified In-Universe — it isn't her real name. She didn't even choose it. The doctor responsible for waking her out of inadvertent cyrosleep named her after his favorite song, "My Funny Valentine."
- Mai Valentine from Yu-Gi-Oh! Her last name is Kujaku (peafowl) in the original, though.
- U.S. President (and Big Bad) Funny Valentine in JoJo's Bizarre Adventure: Steel Ball Run. He is unquestionably a villain, but he turns out to be a (deluded) Well-Intentioned Extremist. Hey... Jesus's corpse blessed him for a reason.
- Saint Seiya and Saint Seiya: The Lost Canvas present a Specter named Valentine, who, although definitely a villain and never redeemed, is extremely loyal and dedicated to his army and his commander.
- The Powerpuff Girls: "The Bride Of Mojo Jojo" (issue #24, DC run) has Mojo looking for love on Valentine's Day because he cannot be "a party of one." But when a dating service fails him, he uses various discards and his own DNA to create a Bride of Frankenstein-style mate. The girls, in the meantime, are entertaining ideas of what kind of mommy they'd want.
- Shakara: Valentine D'Eath is a swaggering, boastful alien Professional Killer.
- The grandfather in Spy Kids (played by Ricardo Montalban) is named Valentin Avellan.
- Kevin Bacon played Valentine "Val" Mckee in Tremors.
- Valentine from MirrorMask isn't romanticized, but he does fit the "anti-hero with a heart of gold" type.
- Gangster Eddie Valentine from The Rocketeer. Technically a bad guy, but throws his hat in with the heroes once he learns his employer is a two-bit Nazi.
- Russian criminal boss Valentin Zukovsky is an ally of James Bond in GoldenEye and The World Is Not Enough who isn't quite evil but not entirely good either.
- Billy Ray Valentine in Trading Places.
- George Valentin, the male lead in The Artist, as an homage to silent screen lover Valentino (see the Real Life section below).
- Val(entine) Kozlowski, the bombardier of the Memphis Belle. He even gets a "bet the women love that!" when the public affairs officer learns his full name.
- Valentine Wolfe, who never met a drug he didn't like, from Deathstalker.
- Robert Heinlein's Stranger in a Strange Land has Valentine Michael Smith.
- Valentine Wiggin from Ender's Game. Valentine is the sweet, empathetic-to-a-fault middle child. This stands in contrast with her brothers psychopath-but-he-grew-up-okay Peter "The Rock (Upon Whom I Found My Church)," Fisher Of Men, and the youngest practically-inhuman-empathy-and-perfect-warrior "Ender," properly Andrew, "brother of Peter," "he-who-insisted-on-being-crucified-on-an-X." You see, their father—the very Catholic John Paul Wigginnote —gave them significant saints' names and secret baptisms, because Ender's Game was written at a time when Card seriously believed that Da Gubbamint might outlaw the practice of religion and succeed under the pretense of population control. This interacts annoyingly with The Great Politics Mess-Up, for reasons that have nothing to do with this trope.
- The heroine of the very first of P. G. Wodehouse's "Blandings Castle" novels, Something Fresh (1915), was named Joan Valentine.
- The real name of reformed safe-cracker Ralph Spencer in O. Henry's "A Retrieved Reformation" is Jimmy Valentine. (The story was filmed twice, in 1915 and in 1928, as Alias Jimmy Valentine.)
- In G. K. Chesterton's "Father Brown" stories "The Blue Cross" and "The Secret Garden," Aristide Valentin [sic] is the Head of the Parisian police. He is also the murderer in the latter.
- The main character of Robert Silverberg's Lord Valentines Castle, and some but not all of the following books in the Majipoor Series.
- Mortal Engines has Thaddeus and his daughter Katherine.
- Valentine de Villefort, the Proper Lady-like daughter of the Count's enemies in The Count of Monte Cristo
- And her counterpart in the anime series Gankutsuou, based on The Count of Monte Cristo.
- Valentine, one of the Two Gentlemen of Verona from the play of the same name by Shakespeare.
- Valentinian in the Belisarius Series. He does not have a particularly romantic outlook on life.
- Becca Valentine from Andromeda.
- Emily Valentine from Beverly Hills 90210.
- Cat Valentine from Victorious.
- Emma Valentine from The Wild Wild West episode "The Night of the Vicious Valentine." She's a villain who pretends to be a matchmaker to steal the inheritances of wealthy men. And she wears heart-themed clothing.
- Valentine Wannop, Christopher Tietjens' love interest in Parade's End.
- Johnny Valentine and his son Greg subvert this as they were both heels for much of their careers.
- In Shirley Valentine, a world-weary housewife named Shirley Bradshaw rediscovers a version of herself who remembers how to live life, represented by her maiden name, Shirley Valentine.
- Jill Valentine, one of the main protagonists of the Resident Evil series.
- Vincent Valentine from Final Fantasy VII.
- Isabella (Ivy) Valentine, from the Soul series. Despite looking and acting like a dominatrix, she's actually one of the heroes, and only helped the villains in her Soulcalibur debut because she was misled into working with them.
- The family of vampires from Shadow Hearts: Keith in the first game, Joachim in Covenant and Hildegard in From the New World.
- Mr. Valentine, the Big Bad arch-criminal from Guilty Party. Fully in-line with the trope, "he" does indeed have a Hidden Heart of Gold.
- Queen Valentina from Super Mario RPG.
- Nurse Valentine from Skullgirls. She's The Dragon to the game's Big Bad, serving her for reasons unknown. Her Story Mode reveals Valentine was forced into serving her after the defeat of the Last Hope, and she was actually a Good All Along Reverse Mole.
- All of the members of the anti-Skullgirls government group Valentine used to be a part of, the Last Hope, were named after different holidays. So of course, the sexiest one was named after the holiday associated with love. Ironically, her character bio reveals that she was born on December 25th.
- Valentine is the name of the Big Bad of Guilty Gear 2: Overture, a mysterious, Ambiguously Human girl hailing from a plane of existence known as the Backyard. She happens to be a clone of the main hero's Lost Lenore, and manages to remember him right as she dies.
- The following installment, Xrd -SIGN-, adds two characters (Ramlethal and Elphelt) whose last names are Valentine, suggesting it's a Species Surname. A fourth Valentine, Jack-O', joins in Xrd -REVELATOR-. Ramlethal and Elphelt are successors to the original Valentine created by their "Mother," the Universal Will; the first makes a Heel–Face Turn after discovering her emotions and own self-value while the second is good-natured from the start, but briefly serves as a Manchurian Agent. Jack-O' was instead made by That Man (the series' presumed but not-quite-Big Bad) to counteract the Universal Will's plans. Ramlethal and Elphelt are suggested to also be clones of Aria—Elphelt even looks identical to her save for a few cosmetic differences. Jack-O' is another dead ringer, but she actually is, for all intents and purposes, the character in question.
- Nick Valentine, the Hardboiled Detective of Fallout 4. Seems an odd choice at first, given that Nick is a Synth with a side order of Body Horror. Becomes Fridge Brilliance however, when you realise that Nick is The Heart.
- Tex Avery's 1936 Warner Bros. cartoon "Don't Look Now" has cherubic and childlike Dan Cupid preparing for February 14 with his bow and arrows. A similarly cherubic and childlike Devil sees the day as a chance to mess up Cupid's efforts with mischief.
- An episode of Here Comes the Grump called "Sugar and Spite" has two opposing lands located next to each other. On one side is the dreary Land of Glum, populated by nasty, misshapen creatures called the Baddies. On the other side is Valentinia, whose inhabitants are cheerful little winged hearts called the Valentines.
- Once famous as the greatest lover in film, Rudolph Valentino.
- The original Saint Valentine.
- Valentine Dyall, best known as the Black Guardian.
- One early example is also a brutal aversion; "Duke Valentino" was one of the titles of Cesare Borgia, who wouldn't even fit into the villainous use of this trope. since he was a straight-up Magnificent Bastard.
- Likely also averted with Valentina (the feminine form) Tereshkova, the Russian Cosmonaut.