Bennett was born in Brooklyn but later moved to Washington, D.C., where he attended Gonzaga College High School. He graduated from Williams College, where he was a member of The Kappa Alpha Society, and went on to earn a Ph.D. from the University of Texas at Austin in Political Philosophy. He also has a J.D. from Harvard Law School.

From 1976 to 1981 he was the executive director of the National Humanities Center, a private research facility in North Carolina. In 1981 President Ronald Reagan appointed him to head the National Endowment for the Humanities, where he served until Reagan appointed him Secretary of Education in 1985. Reagan originally nominated Mel Bradford to the position, but due Bradford's pro-Confederate views Bennett was appointed in his place. This event was later marked as the watershed in the divergence between paleoconservatives, who backed Bradford, and neoconservatives, led by Irving Kristol, who supported Bennett. It was in 1986 that Bennett switched from the Democratic to the Republican party. Bennett resigned from this post in 1988, and later that year was appointed to the post of Director of the Office of National Drug Control Policy by President George H. W. Bush. He was confirmed by the Senate in a 97-2 vote.

Bennett is a member of the National Security Advisory Council of the Center for Security Policy (CSP). He was co-director of Empower America and was a Distinguished Fellow in Cultural Policy Studies at the Heritage Foundation. Long active in United States Republican Party politics, he is now an author, speaker, and, since April 5, 2004, the host of the weekday radio program Morning in America on the Dallas, Texas-based Salem Communications. In addition to his radio show, he is the Washington Fellow of the Claremont Institute. Further work at the Claremont Institute includes his role as Chairman of Americans for Victory Over Terrorism (AVOT). He is also a political analyst for CNN.

Bennett and his wife, Elayne, have two sons, John and Joseph. Elayne is the president and founder of Best Friends Foundation, a national program promoting sexual abstinence among adolescents. He is the brother of Washington attorney Robert S. Bennett.

Bennett tends to take a conservative position on affirmative action, school vouchers, curriculum reform, and religion in education. As Education Secretary, he asked colleges to better enforce drug laws, supported a classical education rooted in Western culture, and derided multicultural courses. He frequently criticized schools for low standards. In fact, in 1988, he called the Chicago public school system "the worst in the nation." Schools and Education

Bennett has tangled with the educational establishment (which he dubbed "the blob" or bloated educational bureaucracy) over the following reform measures, which he espoused:

• Competency testing for teachers
• Opening the teaching profession to knowledgeable individuals who have not graduated from "schools of education"
• Performance-based pay
• Holding educators accountable for how much children learn
• A national examination to find out exactly how much our children know
• Parental choice of schools

Bennett is a staunch supporter of the War on Drugs and has been criticized for his views on the issue. On a television show, he said that a viewer's suggestion of beheading drug dealers would be "morally plausible."

Bennett is an opponent of same-sex marriage.

In 1995, he teamed up with C. Delores Tucker to create advertising to target Time Warner's lack of regulation of gangsta rap and its glorification of violence and denigration of women. Bennett is a member of the Project for the New American Century (PNAC) and was one of the signers of the January 26, 1998 PNAC Letter The Indy Voice..."Be the change you want to see in the world." » Project New American Century sent to President Bill Clinton urging Clinton to remove Iraqi leader Saddam Hussein from power.

Bennett's best-known written work may be A Treasury of Great Moral Stories (1993), which he edited; he has also authored and edited eleven other books, including The Children’s Book of Virtues (which inspired an animated television series) and The Death of Outrage: Bill Clinton and the Assault on American Ideals (1998).

Other books:

• A Century Turns: New Hopes, New Fears (2010)
• The American Patriot's Almanac: Daily Readings on America (2008 with John Cribb)
• America: The Last Best Hope (Volume II): From a World at War to the Triumph of Freedom (2007)
• America: The Last Best Hope (Volume I): From the Age of Discovery to a World at War (2006)
• Why We Fight: Moral Clarity and the War on Terrorism (2003)
• The Broken Hearth: Reversing the Moral Collapse of the American Family (2001)
• The Educated Child: A Parent's Guide from Preschool through Eighth Grade (1999)
• The Index of Leading Cultural Indicators (1999)
• Our Sacred Honor (1997, compilation of writings by the Founding Fathers)
• Body Count: Moral Poverty...and How to Win America's War Against Crime and Drugs (1996)
• Moral Compass: Stories for a Life's Journey (1995)
• The De-Valuing of America: The Fight for Our Culture and Our Children (1992)

Bennett writes for National Review Online, National Review and Commentary.

Bennett is currently the host of Morning in America, a nationally syndicated radio program produced and distributed by Salem Communications. The show airs live weekdays from 6 to 9 a.m. Eastern Time; it is one of the only syndicated conservative talk shows in the morning drive time slot. However, its clearances are limited due to a preference for local shows in this slot, and the show gets most of its clearances on Salem-owned outlets. Morning in America is also carried on Sirius Satellite Radio, on Channel 144, also known as The Patriot Channel

In 2008, Bennett became the host of a CNN weekly talk show, Beyond the Politics. It is unknown whether this will be a limited run or a permanent addition.

Gambling

In 2003 it became publicly known that Bennett was a high-stakes gambler who reportedly had lost millions of dollars in Las Vegas. As a Catholic, Bennett was not prohibited from gambling (although the Catholic Church states that one should be stewards of their money and use moderation) but some felt it conflicted with his public image as a leading voice for conservative morals. Criticism elevated in the wake of Bennett's publication, The Book of Virtues, in which he argued for self-discipline... an attribute at odds with problem gambling. Bennett and Empower America, the organization he co-founded and headed at the time, opposed the extension of casino gambling in the states.

Bennett never said he had a problem with gambling and has maintained that his habit did not put himself or his family in any financial jeopardy. After Bennett's gambling became public, he said that he did not believe that his habit set a good example, that he had "done too much gambling" over the years, and that his "gambling days are over". "We are financially solvent," his wife Elayne told the USA Today. "All our bills are paid." She added that his gambling days are over. "He's never going again," she said.

Several months later, Bennett qualified his position, saying "So, in this case, the excessive gambling is over." He explained that "Since there will be people doing the micrometer on me, I just want to be clear: I do want to be able to bet the Buffalo Bills in the Super Bowl." Are Bill Bennett’s gambling days over or not? - The Carpetbagger Report

Radio show abortion comment

On September 28, 2005, in a discussion on Bennett's Morning in America radio show, a caller to the show proposed the idea that the Social Security system might be solvent today if abortion hadn't been permitted following the Roe v. Wade decision. Bennett responded that aborting all African-American babies "would be an impossible, ridiculous, and morally reprehensible thing to do, but the crime rate would go down."Subsequently, Senate Minority Leader Harry Reid and House Minority Leader Nancy Pelosi, as well as civil rights groups, condemned Bennett's statements and demanded an apology. President George W. Bush said Bennett's statements were "not appropriate."

Bennett responded to the criticism saying, in part:

A thought experiment about public policy, on national radio, should not have received the condemnations it has. Anyone paying attention to this debate should be offended by those who have selectively quoted me, distorted my meaning, and taken out of context the dialog I engaged in this week. Such distortions from 'leaders' of organizations and parties is a disgrace not only to the organizations and institutions they serve, but to the First Amendment.