[2] His father, Jack Wills, was from a Protestant background, and his mother was from an Irish Catholic family.

William F. Buckley Jr. hired him as a drama critic for National Review magazine at the age of 23.

[5] Wills was married for sixty years (1959–2019) to Natalie Cavallo, a collaborator and photographer for his work.

[4][7] After his wife's death in 2019 and the sale of their house, he donated most of his library to Loyola University Chicago, but retained what he termed "the core".

[10] In a May 2024 interview with the Chicago Tribune, Wills revealed that he no longer considers himself a Catholic nor takes communion.

[11][12][13][14] In 1961, in a phone conversation with William F. Buckley Jr., Wills coined the famous macaronic phrase Mater si, magistra no (literally "mother yes, teacher no").

[9] The phrase, which was a response to the papal encyclical Mater et magistra and a reference to the then-current anti-Castro slogan "Cuba sí, Castro no", signifies a devotion to the faith and tradition of the church, combined with a skeptical attitude towards ecclesiastical–Church authority.

However, during the 1960s and 1970s, driven by his coverage of both civil rights and the anti-Vietnam War movements, Wills became increasingly liberal.

[18] Instead, Wills argued that the Second Amendment refers to the right to keep and bear arms in a military context only, rather than justifying private ownership and use of guns.

Modern militias say the government itself instructs them to overthrow government—and wacky scholars endorse this view.

According to this doctrine, a well-regulated group is meant to overthrow its own regulator, and a soldier swearing to obey orders is disqualified from true militia virtue.The New York Times literary critic John Leonard said in 1970 that Wills "reads like a combination of H. L. Mencken, John Locke and Albert Camus.