At Nixon's urging he attended the University of Michigan Law School, where he was inducted into the Order of the Coif.

degree in 1983, then moved to Washington, D.C., to clerk for Judges Roger Robb and George MacKinnon on the U.S. Court of Appeals for the District of Columbia Circuit in 1983–84.

Hewitt suggested refusing admission to researchers deemed "unfriendly" – specifically Bob Woodward, whom he characterized as "not a responsible journalist."

Hewitt received three Emmys for his work on Life & Times on KCET,[13] and also conceived and hosted the 1996 PBS series Searching for God in America.

[24] Although Hewitt's background is in law, government, and politics, he also covers American cultural trends and the entertainment industry.

He frequently critiques the mainstream media on air, often inviting journalists to defend their work on the show.

On June 24, 2017, Hugh Hewitt debuted, a half-hour television show which ran on MSNBC in the Saturdays 8 am EST timeslot.

[26] On Saturday, June 30, 2018, Hewitt announced that the show had been cancelled, but that he would continue his commentary on the NBC family of networks.

In November 2024, Hewitt quit his position with The Washington Post following an appearance on the paper's live show.

[30] In a 2006 interview on CNN with Anderson Cooper, Hewitt said that in regards to George W. Bush's decisions while President, the War in Iraq would go down as "one of the wisest he has made.

"[31] In regard to the Syrian Civil War, Hewitt stated that President Donald Trump was making a "major error" in deciding to draw down the number of U.S. troops in the country, over seven years after the beginning of the conflict.

[30] In February 2016, Hewitt wrote that, despite being repeatedly publicly insulted by Trump, he would support him should he become the Republican nominee for president.

[37] Internal emails showed that a Salem Media executive pressured Hewitt to support Trump, and that the Salem Media executive attributed Hewitt's support for Trump in the aforementioned Washington Post op-ed shortly after to the pressure.

[41] Hewitt supported Trump's decision to re-shuffle his foreign policy staff in March–April 2018, and place John Bolton and Mike Pompeo in key national security positions.

[42][30] He described John Bolton, a zionist hawk, as "peace-through-strength, 600-ship [navy], Reagan conservative" (as compared to Trump's approach, which Hewitt likened to the Great White Fleet).

[45] He described the July 25 phone call in which Trump requested that Ukrainian President Volodymyr Zelenskyy investigate Joe Biden, a 2020 Democratic presidential candidate, as a "nothingburger".