Created by McGruder in 1996 for Hitlist.com, an early online music website,[1] it was printed in the monthly hip hop magazine The Source in 1997.

As it gained popularity, the comic strip was picked up by the Universal Press Syndicate and made its national debut on April 19, 1999.

It later appeared in the University of Maryland newspaper The Diamondback[3] under editor-in-chief Jayson Blair[4] on December 3, 1996, paying McGruder $30 per strip—$17 more than other cartoonists.

[14] In February 2019, a series of one-shot strips were published on radio personality Charlamagne tha God's Instagram page.

The title word "boondocks" alludes to the isolation from primarily African-American urban life that the characters feel, and permits McGruder some philosophical distance.

Their grandfather Robert is a firm disciplinarian, World War II veteran, and former civil rights activist who is offended by both their values and ideas.

Their young daughter Jazmine is very insecure about her ethnic identity and is often the subject of Huey's antipathy for being out of touch with her African ancestry.

The Boondocks was very political and occasionally subject to great controversy, usually sparked by the comments and behavior of its main character, Huey.

The content of McGruder's comic strip often came under fire for being politically left-wing and occasionally risqué, leading to its being published in the op-ed section of many newspapers.

The Boondocks garnered significant attention after the September 11th attacks with a series of strips in which Huey calls a government tipline to report Ronald Reagan for funding terrorism.

[18][19][20] For example, the "Condi Needs a Man" strip, in which Huey and his friend Caesar create a personal ad for U.S. Secretary of State Condoleezza Rice, portraying her as a "female Darth Vader type that seeks loving mate to torture", resulted in The Washington Post withholding a week's worth of strips, the longest such suspension ever by the paper.