Bailey is known for his literary biographies of Richard Yates, John Cheever, Charles Jackson, and Philip Roth.

Bailey and his family lost their house and most of their possessions in Hurricane Katrina, an experience he wrote about in a series of articles for Slate.

In an interview with The New York Times published on November 17, 2012, Philip Roth said that Bailey was his official biographer and at work on that project.

[8] While Roth was alive, he gave Bailey exclusive access to papers, friends and family, and made himself available for extensive interviews.

One of the women accused Bailey of “grabbing her crotch in a hot tub, forcibly trying to kiss her on campus, [and] threatening to rape her".

Another account in the Virginian-Pilot's report concerned a female author who visited Old Dominion and described Bailey as having forcibly kissed her.

[21][22] In a statement provided to the Associated Press on April 21 by W. W. Norton & Company, the publisher announced it had "decided to pause the shipping and promotion of Philip Roth: The Biography pending any further information that may emerge.