* Billy Preston references this trope in his song "Will It Go Round in Circles":
-->"I got a story, it ain't got no moral,\\
Let the bad guy win every once in a while."
* PlayedForLaughs in Sophie Ellis-Bextor's "[[http://www.youtube.com/watch?v=BsISfQAXE60 Murder on the Dance Floor]]." The BitchInSheepsClothing sabotages all the other dancers for a competition, and bribes the judge. She looks really happy when she wins.
* The theme of rapper Common's single "Testify": The man on trial is a petty drug dealer accused of a shooting. His wife is extremely distraught and disruptive in the courtroom and when he is found guilty she seems to break down.... [[spoiler: until it is revealed she is a criminal "queenpin" who set her husband up to take the fall for the murder she committed. The dramatic outbursts in the courtroom were entirely for show.]]
* In ''Music/TheProtomen'' 's rock opera based on the Mega Man video games, Dr. Wily is on top in both acts, the heroes dying out or just plain giving up. Joe is dead in Act II, Protoman defected to Wily's side and is killed, and Megaman abandons the city at the end of Act I. Only Act III will tell if he truly wins his battle.
* In Dave Alvin's "Mary Brown", [[FemmeFatale the titular Bad Gal]] convinces the protagonist to kill her abusive husband, lets him take the rap by lying in court, and ends up marrying her dead husband's best friend. At the end of the song, the still-lovestruck dope complains that even though she never returns his letters, [[WhatAnIdiot he still loves her]].
* 3OH!3's "Bad Guy" tells the story of [[WouldNotShootAGoodGuy good guys getting shot dead]]. The chorus goes "Gather up your loved ones, gather up your friends, 'cause this is when the bad guy, {{the bad guy wins}}!", actually name-dropping the trope.