Assassins plays this for laughs by having Lynette Froome wax lyrical about how amazingly smart and beautiful Charles Manson is. Based on Real Life, as she was infatuated with Manson and tried to kill the President in his name.
In Grease, the "cool" girls, especially Rizzo, are attracted to bad boys, and the male lead, Danny Zuko, is a bad boy who resembles Arthur Fonzarelli. The main conflict in the plot is over Danny's "badness" and the "goodness" of Sandy, the lead female. Eventually, they end up meeting somewhere in the middle.
In Spring Awakening Thea declares, "Melchi Gabor, he's such a radical! You know what the whisper is? He doesn't believe in anything! Not in God, not in Heaven, not in a single thing in this world!" Cue the other girls on stage sighing dreamily.
Stella in A Streetcar Named Desire chooses to stay with Stanley, who is violent, abusive, and beneath her social class. She reasons that what goes on between the sheets makes everything unimportant. Even her sister Blanche flirts with him.
"Mack The Knife" Macheath in Kurt Weills The Threepenny Opera is an all-out sociopathic criminal. But that does not stop at least four girls from going crazy over him.
Zombie Prom sort of parodies this with The Hero, Jonny Warner. He has a motorcycle (like many bad boys), but the most rebellious thing he does is take the "h" out of his name, then tell Miss Strict he'd prefer to keep it out. Miss Strict and Toffee's parents still insist she break up with him. When she does, he is Driven to Suicide, then comes back as a zombie. Interestingly, once he does, it is suggested that he might have been a bit more rebellious than we thought (telling Miss Strict that he "used to hate [her]" and "could not be reached"), but, as a zombie, all he wants to do is return to school and take Toffee to the prom.
Sarah of Tanz Der Vampire is a lot more interested in the vampire Count von Krolock than she is in Alfred, the quintessential (human) Dogged Nice Guy. She spends the musical longing for the Count's bite even as Alfred sings of his love for her.
Deconstructed in Heathers. Veronica was very much attracted to bad boy J.D. when he was just a broody, intense bookworm with a troubled past that beat up Jerk Jocks in the cafeteria. Once he starts murdering people, however, their relationship goes south.
The Mrs Hawking play series: Subverted with Arthur the policeman. He's just about the sweetest, most straightforward guy you could imagine, and he's presented as a romantic and attractive figure for lead character Mary.
Elisabeth: As far as bad boys go, it doesn't get worse than killing two of your children and saying point blank that he will own you in the end. In fact, it's after he did it the second time that Elisabeth breaks and begs Death to take her. The German tour and Raimund Theater revival amped it up by giving Death the Hell-Bent for Leather trope. note Which was a version of Actor-Inspired Element, as the androgynous costume used for previous Deaths does not look flattering on ultra-masculine Mark Seibert. Takarazuka productions also took note of this sartorial change.