After college, Bailey wrote occasional freelance pieces. He taught gifted eighth-graders at
Lusher Middle School in New Orleans in the 1990s. After publishing a long critical profile of
Richard Yates, Bailey was contracted to write a full-length biography of the novelist,
A Tragic Honesty: The Life and Work of Richard Yates (2003). In 2005, Bailey was awarded a
Guggenheim Fellowship to work on his biography,
Cheever: A Life, which won the 2009
National Book Critics Circle Award among other honors. Bailey also edited a two-volume edition of Cheever's work for the
Library of America. Bailey published his biography of the novelist
Charles Jackson,
Farther & Wilder: The Lost Weekends and Literary Dreams of Charles Jackson (2013), as well as a memoir,
The Splendid Things We Planned: A Family Portrait (2014). 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. While Roth was alive, he gave Bailey exclusive access to papers, friends and family, and made himself available for extensive interviews. Bailey's 880-page biography of Roth, entitled
Philip Roth: The Biography, was published in the United States by W. W. Norton & Company on April 6, 2021, and in the United Kingdom by Jonathan Cape on April 8, 2021. Bailey's primary influence is
Lytton Strachey, who he has praised for his style and sense of humor. Other influences on Bailey's work include
Vladimir Nabokov,
Evelyn Waugh, and
PG Wodehouse. == Sexual misconduct allegations ==