Ruben Bolling is a five-time winner of the Association of Alternative Newsweeklies Award for Best Cartoon, for 2002, 2003, 2007, 2008, and 2009. In 2010, he received the
Society of Professional Journalists award for Editorial Cartooning for a non-daily publication. He won numerous awards for his satirical criticism of the
Donald Trump presidency. He was the winner of the 2017
Herblock Prize for editorial cartooning based on a selection of 15 Trump-themed
Tom the Dancing Bug cartoons. In 2017, he won a 2017 Silver Reuben Award from the
National Cartoonists Society for "Donald and John," a series in the style of
Calvin and Hobbes that cast
Donald Trump as a childish Calvin-like figure and
Trump alter-ego John Barron as Trump's "imaginary publicist" in place of Hobbes. He was awarded a prize for best cartoon in the 2018
Robert F. Kennedy Journalism Award. In 2019 and 2021 Ken Fisher was a finalist in the Editorial Cartooning category for the
Pulitzer Prize. For "mordant wit, superior artwork, and inventive delivery" Ruben Rolling won the 2021 Berryman Award for Editorial Cartoons from the
National Press Foundation. Ruben Bolling won the
National Cartoonists Society's Reuben Award for Editorial Cartoons in 2022 and was nominated again in 2023. == Personal life ==