Anderson graduated from Ohio State University.[2] After interning at the Louisville Courier Journal, he became the newspaper's editorial cartoonist in c. 1990.[2]
Soon after winning the 2005 Pulitzer Prize for Editorial Cartooning, his winning cartoons were shown on air by Fox News' Sean Hannity as evidence, Hannity argued, of liberal bias by the Pulitzer judges.[3]
Anderson was staff cartoonist for the Houston Chronicle from 2006 to 2017, where the newspaper's website maintained a blog[4] of his cartoons and video animations.
The CNN-YouTube Republican presidential debates, which aired on November 28, 2007, used one of Anderson's questions, submitted in animated form.[5]
Anderson was president of the Association of American Editorial Cartoonists[6] in 2007–2008.[7]
As of 2013, Anderson was syndicated in 150 newspapers by The Washington Post Writers Group.[1]
In the summer of 2017, Anderson was terminated from his position at the Houston Chronicle;[2][6] up to that point, he had been the last staff editorial cartoonist in the entire state of Texas.[8][6]
In late 2020, Anderson's cartoons began being syndicated by the Tribune Content Agency.[9]
In 2018, some time after losing his position at the Houston Chronicle, Anderson and a partner[10] formed Counterpoint Media, launching a website and newsletter that featured a rotating group of editorial cartoonists.[11][2][10]
In 2022, The Washington Post Writers Group announced it was winding down its editorial cartoons syndication business. In response, a number of the syndicate's editorial cartoonists — including Clay Bennett, Jack Ohman, and Pedro X. Molina — left for Counterpoint Media, which launched its own syndication service.[11]
In September 2022, Counterpoint began syndicating comic strips, first taking on Darrin Bell's Rudy Park[12] and then Gene Weingarten, Dan Weingarten, and David Clark's Barney & Clyde,[13] both of which were formerly distributed by The Washington Post Writers Group.
Degg, D. D. (April 23, 2023). "The Funnies This Past Week – updated". The Daily Cartoonist. Well it seems that Counterpoint is syndicating the Rudy Park comic strip now, and has been for quite some time! I traced the switch from Washington Post Writer's Group to Counterpoint Media to September 1, 2022.