He described his household as normal and "apolitical", in considerable contrast to his father's flamboyant public persona as a conservative icon, who once denounced rock music as a "Pavlovian Communist mind-control plot" and wrote speeches for George Wallace.

Allen moved east to attend Washington and Lee University, graduating in 1986 with a double major in politics and journalism.

[6][7] At Politico, a Washington-based print and online publication launched by Allbritton Communications, Allen wrote the daily "Playbook.

[1] Allen was featured in a piece for the April 25, 2010, edition of The New York Times Magazine titled, "The Man the White House Wakes Up To."

"[13] In 2004, Allen won the White House Correspondents' Association's Merriman Smith Memorial Award for outstanding presidential coverage on deadline.