He wrote a book of cultural commentary titled Bobos in Paradise: The New Upper Class and How They Got There, published in 2000, and followed it four years later with On Paradise Drive: How We Live Now (And Always Have) in the Future Tense.

Brooks was a visiting professor of public policy at Duke University's Terry Sanford Institute of Public Policy, and he taught an undergraduate seminar there in the fall of 2006.

He and his wife live in Bethesda, Maryland. Brooks is Jewish.

Brooks describes himself as being originally a liberal before "coming to my senses." In 1983, he wrote a parody of conservative pundit William F. Buckley, Jr., which said "In the afternoons he is in the habit of going into crowded rooms and making everybody else feel inferior. The evenings are reserved for extended bouts of name-dropping."

Buckley admired the parody and offered Brooks a job with National Review. A turning point in Brooks's thinking came later that year in a televised debate with Milton Friedman, which, as Brooks describes it, "was essentially me making a point, and he making a two-sentence rebuttal which totally devastated my point".

Before the 2003 invasion of Iraq, Brooks argued forcefully for American military intervention, echoing the belief of conservative commentators and political figures that American and British forces would be welcomed as liberators. In the spring of 2004, some of his opinion pieces suggested that he had tempered his earlier optimism about the war.[citation needed]

On August 10, 2006, Brooks wrote a column for The New York Times titled "Party No. 3". The column proposed the idea of the McCain-Lieberman Party, or the fictional representation of the moderate majority in America.

Many in the "conservative movement," such as Rush Limbaugh and Mark Levin, denounce him as he frequently runs to their left. He has long been a supporter of John McCain; however, Brooks did not show a liking for Governor Sarah Palin, who ran with McCain on the 2008 Republican presidential ticket, calling her a "cancer" on the Republican Party. He recently referred to her as a "joke," unable to ever win the Republican nomination.

In a March 2007 article published in The New York Times titled "No U-Turns", Brooks explains that the Republican Party must distance itself from the minimal-government conservative principles that had arisen during the Barry Goldwater and Ronald Reagan eras. He claims that these outdated concepts had served their purposes and should no longer be embraced by Republicans in order to win elections.

Breaking with his fellow conservatives, Brooks has been a frequent admirer of President Barack Obama. In an August, 2009 profile of Brooks, The New Republic describes his first encounter with Obama, in the spring of 2005: "Usually when I talk to senators, while they may know a policy area better than me, they generally don’t know political philosophy better than me. I got the sense he knew both better than me. [...] I remember distinctly an image of--we were sitting on his couches, and I was looking at his pant leg and his perfectly creased pant, and I’m thinking, a) he’s going to be president and b) he’ll be a very good president.” Two days after Obama’s second autobiography, The Audacity of Hope, hit bookstores, Brooks published a column in The New York Times, entitled "Run, Barack, Run", urging Obama to run for president.