It's pretty common to hear people say that they're so disgusted with American politics that they're going to move to Canada and renounce their U.S. citizenship... especially if candidate X or Y wins the election. But people almost never follow through with this threat/promise.
But Joel Slater did. Back in the Reagan era (1987), he became so angry at U.S. policies that he decided to renounce his American citizenship. The problem was that he did this without first arranging to acquire citizenship in another country. So he made himself stateless.
He was in Australia when he renounced his citizenship, and had assumed he would be able to stay there. But no, Australia promptly deported him to the U.S. Then, as a stateless person, he discovered that he was effectively trapped in the U.S. because he couldn't travel anywhere else without a passport. He managed to make it into Canada and Mexico a few times without a passport, but they both eventually shipped him back to the States. He also couldn't legally work without a social security number. So he became homeless, surviving on "odd jobs and the generosity of strangers."
After much begging and pleading, he was able to regain his U.S. citizenship in 1993.
More info: wikipedia
Slater showing off his "Certificate of Loss of Nationality of the United States"
Source: Arizona Republic - Mar 17, 1991
Indianapolis Star - Nov 27, 1992