He entered and then left the Jesuit order. William F. Buckley, Jr. hired him as a drama critic for National Review magazine at the age of 23. He received his PhD in classics from Yale in 1961. Wills has been awarded the honorary degree of L.H.D. by the College of the Holy Cross (1982) and by Bates College (1995).

Ideologically, he started out his adult life as a conservative, but through the 1960s he became more and more a liberal, driven by covering the civil rights movement and the anti-Vietnam War movement.

His biography of president Richard M. Nixon, Nixon Agonistes (1970) landed him on the master list of Nixon political opponents.

Wills joined the faculty of the history department at Northwestern University in 1980. He is now an emeritus professor.

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