James Madison's first appearance in the musical (besides "Alexander Hamilton") is at the end of Act One, when Aaron Burr is telling the audience about how Alexander Hamilton exceeded expectations and wrote 51 essays for The Federalist Papers, and mentions that Madison wrote twenty-nine of the eighty-five essays ("Non-Stop").
After Thomas Jefferson returns from France after a long break, Madison greets him and pleads him to help in the political struggle he is going through. Madison claims that Hamilton's financial plan was a heist of power, given to the government. ("What'd I Miss"). Thomas Jefferson promptly confronts Hamilton in a cabinet battle and in an argumentative manner reminds him that he will need congressional approval before the plan goes through. Madison agrees and comments that it would be difficult without his and Jefferson's agreement ("Cabinet Battle 1").