He is best known as a performance artist or "media prankster" who filed an application in 1997 to register the phrase "Freedom of Expression" as a trademark in the United States. This phrase was the name of his zine/artist book series, and on January 6, 1998, McLeod was granted registration no. 2127381 in Class 16 (for "booklets in the field of creative writing").
McLeod sought registration of the phrase "Freedom of Expression" as a reflection on the use of intellectual property law to restrict cultural expression in U.S. society. In 2003, McLeod sent AT&T a cease and desist letter in response to an AT&T advertising campaign in college newspapers promoting a new long distance plan which used the phrase "freedom of expression". McLeod claimed that the use by AT&T of his registered trademark could lead some consumers to infer a connection between his publication and AT&T. The New York Times later interviewed McLeod, and reported that his aim was "to object to corporate power over words, speech and even ideas. 'I do want to register my genuine protest that a big company that really doesn't represent freedom of expression is trying to appropriate this phrase,' he said."
Registration no. 2127381 was cancelled in October 2004 when McLeod did not lodge documentary evidence with the United States Patent and Trademark Office to demonstrate that "Freedom of Expression" had been used as a trademark.
On December 10, 2007, McLeod protested a Bill Clinton event in Iowa City, Iowa, dressed as a robot and demanding an apology for remarks made by Clinton in 1992 about controversial hip hop musician Sister Souljah. Before being removed by security and as he was led away, McLeod tossed multi-colored flyers into the air which included the name of a website, mr-ifobca.org, standing for "Mad Robots in Favor of Bill Clinton Apologizing."
McLeod's book built upon the themes raised by the AT&T event and develops a serious critique on a range of diverse topics such as hip-hop music and sampling, the patenting of seeds and human genes, folk and blues music, visual collage art, electronic voting, and computer software, among other things.
McLeod has also written music criticism for Rolling Stone, The Village Voice, Spin, and Mojo. He is the coproducer of a 2001 documentary film on the music industry, Money for Nothing: Behind the Business of Pop Music, which he produced for the Media Education Foundation. He is currently working on another documentary on the history of sound collage, digital sampling, and intellectual property law, titled Copyright Criminals: This Is a Sampling Sport."
He participated in the exhibition "Illegal Art: Freedom of Expression in the Corporate Age," which was hosted by the San Francisco Museum of Modern Art's Artist Gallery. In 2005, he helped co-found the Freedom of Expression® Security Consortium, which is dedicated to "Regulating Freedom of Expression in the Marketplace of Ideas". He also is co-editor (with Ted Striphas) of a 2006 special issue of the journal Cultural Studies on "The Politics of Intellectual Properties," which is available for free on the internet.