Formerly a Republican U.S. Senator—he represented New York from 1981 to 1999—D'Amato is now a lobbyist and speaker-for-hire.

The Brooklyn native and law school graduate waited just two years after passing the bar before running for his first political office—Nassau County Public Administrator—in 1965. He moved through the ranks, from administrator to tax assessor to supervisor, before defeating U.S. Senator Jacob Javits in the 1980 Republican primary election and winning the seat. D'Amato served in the Senate from 1981 to 1999, during which time he became known as Senator Pothole for his tendency to spend government money on individual constituents' petty problems. He also earned a reputation for his opposition to taxes and for his own questionable ethics. He was defeated in an upset by Democrat Chuck Schumer in 1998. D'Amato has since founded his own consulting and lobbying firm, Park Strategies. He also works the lecture circuit.

D'Amato and his first wife, Penelope, with whom he had four children, officially divorced in 1995, although by that point they'd been separated for 13 years. During the '90s, D'Amato dated the late gossip columnist Claudia Cohen as well as Candace Bushnell. He eventually settled down with Katuria Elizabeth Smith, and the pair has two children. [Image via Getty]