|“||My expectations were a lot higher... But at least I saved the rubles on the garrote wire.||„|
|~ Ivan the Terrible after dealing with Frederick the Great|
He was portrayed by Nice Peter who also plays Darth Vader in the Darth Vader vs. Adolf Hitler trilogy, Grigori Rasputin, Vladimir Lenin and Vladimir Putin in Rasputin vs. Stalin.
Alexander the Great Vs. Ivan the Terrible
Ivan the Terrible appeared as a major antagonist of the battle, starting as any other rapper - challenging Alexander. However, while the latter was rapping, Ivan took his idea of himself to "go and fix [him] a drink". As the Alexander finished his verse, Ivan "acknowledged" his defeat and gave the winner a cup with poisoned wine, taking the action into his dungeon where Alexander dies.
However, Frederick the Great took up the place of the fallen conqueror, giving a verse. This time Ivan tricked his opponent into offering Fred the seat he ordered him to bring, intending to strangle him. However, as Ivan checked it, it appeared the Fredrick died in his seat like his historical counterpart.
Pompey the Great was intending to take his place, however, russian empress Catherine the Great took his place since "it takes a Russian to take down a Russian". Once she finished her first verse Ivan insulted her by offering her a horse as a reference to a rumor that she died while sexually involving with a horse. She is unfazed and continues on to her second verse finishing the battle with a chess checkmate, where Ivan's historical counterpart died.
- A preview of Ivan was shown during the end slate of another battle before the actual appearance of him.
- Ivan's one of a few rappers of the series to have non-rapping lines.