Allen grew up in Orange County, California. He graduated from Washington and Lee University in 1986, with a double major in politics and journalism.

His first reporting job was with the Fredericksburg Free Lance-Star. He has also worked at the Richmond Times-Dispatch, the Washington Post, the New York Times and Time.

At The Politico, a Washington-based print and on-line publication launched by Allbritton Communications, Allen writes the daily “Playbook.” The Politico - Politico.com.

Allen was featured in a piece for the April 25, 2010 edition of the New York Times Magazine entitled, "The Man the White House Wakes Up To". He is considered by many to be one of the most powerful and influential journalists in Washington.

Allen is the son of right-wing conspiracy theorist and John Birch Society member Gary Allen.

In 2004, Allen won the White House Correspondents' Association’s Merriman Smith Memorial Award for outstanding presidential coverage on deadline. The award was given to Allen for his reporting of President George W. Bush’s secret trip to Baghdad, Iraq. Journalism and Mass Communications-Washington and Lee University