Woodward grew up in Wheaton, a suburb of Chicago, where his father was a prominent jurist. It was thought that he would follow his father into the legal profession when he enrolled at Yale University on a naval Reserve Officers' Training Corps (ROTC) scholarship. After receiving a bachelor's degree in history and English literature in 1965, Woodward began a five-year tour of duty as a communications officer. Upon his return, he was accepted (1970) at Harvard Law School. He chose not to pursue a law degree, however. Instead, he petitioned the editors of The Washington Post for an unpaid two-week internship. While none of the stories he submitted was printed, the editors saw potential in the aspiring reporter and referred him to the Montgomery County Sentinel, a weekly paper in suburban Maryland. Within a year Woodward had polished his skills enough that the Post was willing to give him another chance.

Woodward had been covering the police beat for nine months when a call came in about a burglary at the Democratic National Committee headquarters at the Watergate complex. Working with Bernstein, a fellow Post reporter, Woodward eventually connected the break-in to the highest levels of the administration of U.S. Pres. Richard Nixon (Nixon, Richard M.). For Woodward and Bernstein's reporting, the Post was awarded the 1973 Pulitzer Prize for public service. The names Woodward and Bernstein became virtually synonymous with investigative journalism, and their book, All the President's Men (1974), topped the best-seller list. The 1976 film version of the book, with Woodward portrayed by Robert Redford (Redford, Robert), was also a success.

Woodward continued his work at the Post and was named assistant managing editor in 1979. In the following years, however, he became better known for his books than for his newspaper reporting. Exposés on personalities as varied as comedian John Belushi and former U.S. vice president Dan Quayle (Quayle, Dan) drew both admiration and criticism, with reviewers praising his ability to unearth volumes of information while disparaging his tendency to dwell on sordidness. His later material, however, focused on hard news and the power and politics of Washington. He led a team that earned another Pulitzer for the Post in 2002 for the paper's coverage of the repercussions of the September 11 attacks in the United States in 2001. That year he released the first in a series of books that offered an insider's look at the administration of Pres. George W. Bush (Bush, George W.). Bush at War (2002) profiled the personalities who shaped the American military response in Afghanistan, while Plan of Attack (2004) covered the period leading up to the U.S.-led invasion of Iraq. (See Iraq War.) State of Denial (2006), a departure from the generally complimentary tone found in the previous two works, provided a scathing dissection of the missteps and unheeded advice that continued to undermine the administration's war efforts. His fourth volume on the Bush administration, The War Within (2008), offered a harsh assessment of the president.