Kanye West raised some eyebrows when he announced his plans to run for president in 2020 on Sunday night — and he even inspired a Ready for Kanye PAC to coach along his nascent White House bid (as a Republican). If Kanye's ambitions and announcement speech sound familiar, Jimmy Kimmel had a theory why on Monday's Kimmel Live. West "has a great deal in common with another famous person who wants to be president," Kimmel said.