Perhaps pioneered by Epic Rap Battles of History, rap battles have been a popular and musical way to cross over characters and have them face off. This, of course, also includes villains. This category can be a rap battle between two villains, a villain and a hero/neutral, ect.
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- Santa vs Satan
- Shaka Zulu vs Julius Caesar
- Siren Head Vs. Cartoon Cat
- Siren Head Vs. Slender Man
- Six vs Wirt
- Skibidi Toilet vs Learning With Pibby
- Slender Man Vs. Baldi's Basics
- Slender Man vs. Herobrine
- Slender Man vs. Insanity Wolf
- Slender Man vs. Unwanted House Guest
- Slenderman vs. Herobrine Part 2
- Sniper Vs. Widowmaker (VideoGameRapBattles)
- Steve Jobs vs Bill Gates
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