He immersed himself in the world of graphic design at the age of 14 by creating images that were printed on t-shirts and skateboards. Influenced by the works of Andy Warhol and Russian artist Alexandre Rodchenko, he naturally gravitated towards art studies.
In the late 1980s, Obey and a group of friends from the Rhode Island School of Design created a series of stickers and posters featuring the wrestler André the Giant, which they clandestinely plastered on the walls of American cities. This was one of the first and most important "viral" Street Art campaigns, showcasing the powerful impact of this new form of clandestine expression.
His work gained worldwide recognition during the 2008 US presidential campaign with the creation of Barack Obama's HOPE poster, which became an iconic image of the campaign. The President personally thanked him for the influence his poster had during the presidential elections. The Institute of Contemporary Art in Boston considers him one of the best and most influential Street Art artists of the moment.
However, despite being one of the pioneers of street art, his works are sometimes considered to infringe upon artistic property rights by the law. Despite some legal troubles, this has not prevented his exhibitions in various museums from doubling in attendance.