10 Best Epic Rap Battles Of (Actual) History

4. Alexander The Great Vs. Ivan The Terrible (And Others)

Unlike the other five-way showdowns that are bunched together on this list, this one didn't move from character to character, but instead focused on Ivan's journey through finding a worthy 'Great' who could equal his 'Terrible'. Zach Sherwin's verse as Alexander The Great was incredibly verbally dextrous and catalogued many of Alexander's conquests and achievements across the ancient world in just a few bars. Ivan responds by poisoning him and gloating over his body, asking if there is any 'Great' who could defeat this Russian?

Frederick the Great isn't as well known a figure in history, but was King of Prussia from 1712 to 1786 and helped to reform the nation into the one that would eventually become the heart of modern Germany. His military skill was matched by his interest in art and philosophy. Ivan, impressed, offers Frederick a chair and makes to garotte him to death, only to find that (in accordance with his real life death), Frederick has simply died on him.

Ivan's next challenger is Pompey the Great, one third of the Roman Triumvirate. Although Pompey is a hugely influential historical figure, the battle pushes him to one side in order to reveal Ivan's true opponent. And she's right, it takes a Russian to take down a Russian.

Contributor

Still bitter that Star Trek Enterprise got canned and almost old enough to angrily tell the kids to 'Get Off My Lawn!'