Weingarten and his son Dan also write Barney & Clyde, a comic strip with illustrations by David Clark.

He grew up in the southwest Bronx, the son of an accountant who worked as an Internal Revenue Service agent and a schoolteacher.

[5] In 1968, Weingarten graduated from The Bronx High School of Science[7] and attended New York University, where he started as a pre-med student but ended up majoring in psychology.

In 1984, he hired Dave Barry, giving one of America's best-known humor columnists his big break.

[1] Weingarten wrote "Below the Beltway," a weekly humor column for The Washington Post that was nationally syndicated.

[17] Weingarten hosted a popular Washington Post online chat called "Chatological Humor," formerly known as "Tuesdays with Moron."

Common topics in his online chat include the art of comic strips, analysis of humor, politics, philosophy, medicine, and gender differences.

Many of his columns addressing gender differences have been written in a he-said, she-said style in collaboration with humorist Gina Barreca, his co-author for I'm with Stupid.

[19] In his live online chat on June 22, 2009, Weingarten disclosed that he had accepted a buyout offer from The Washington Post, which meant he was retiring as a longer-form feature writer.

[1][25] Weingarten co-wrote a series of humor columns in The Washington Post with feminist writer Gina Barreca about the differences between men and women.

[28] In June 2010, Weingarten and his son Dan began publishing the syndicated comic strip Barney & Clyde, illustrated by David Clark.

[29][30] The comic is about the friendship between billionaire, J. Barnard Pillsbury, and a homeless man named Clyde Finster.

[31] The comic took over five years to develop, with the Miami Herald, The Washington Post, and the Chicago Tribune early supporters.

In 2008, Weingarten was awarded the Pulitzer Prize for Feature Writing for his Washington Post story, "Pearls Before Breakfast,"[37] "his chronicling of a world-class violinist (Joshua Bell) who, as an experiment, played beautiful music in a subway station filled with unheeding commuters.

"[3][38] The night Weingarten returned from accepting his Pulitzer Prize, he received an email from a librarian named Paul Musgrave from the Richard Nixon Presidential Library, who told him that he had recently seen an article about a similar experiment that the Chicago Evening Post did in May 1930 where they had the virtuoso Jacques Gordon play his Stradivarius violin outside a subway station to see if commuters would notice the music.

[45][46][47] Celebrities of South Asian descent Meena Harris, Mindy Kaling and Salman Rushdie also publicly criticized the piece.

[48][49][50] On August 23, the Post added a correction to the article which clarified, "India’s vastly diverse cuisines use many spice blends and include many other types of dishes.

[52] Since 2001 he has lived in the Capitol Hill neighborhood of Washington, D.C.,[53] with his wife, Arlene Reidy, an attorney, but in a column published August 10, 2017, announced that the marriage had collapsed.