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Rosen was born in Brooklyn and raised in nearby Staten Island. He attended Johns Hopkins University in the late 1980s, graduating with a bachelor of arts degree in political science. He then attended the Medill School of Journalism at Northwestern University, graduating with a master's degree.
Rosen joined Fox News as an on-air correspondent in February 1999. According to his Fox News biography, he has since reported "from 49 states and more than three dozen foreign countries across five continents".
In January 2003, Rosen was named the "Funniest Celebrity in Washington" at the annual "Funniest Celebrity in Washington Contest" charity event, after performing a comedy routine that included imitations of George W. Bush, Donald Rumsfeld, Helen Thomas and Tom Brokaw, among others.
In 2008, Rosen's book, The Strong Man: John Mitchell and the Secrets of Watergate was published by Doubleday; it was a biography of Richard Nixon's Attorney General John N. Mitchell, and his involvement in the Watergate scandal. Rosen had spent 17 years researching and writing the book; the project was initially based on a grant Rosen had received from William F. Buckley, soon after graduating from journalism school, to write the book.