While in school, Fairey held a part-time job in a skateboarding shop; the job fit well with the budding artist's interest in street culture and graffiti. During this time, the artist was also interested in punk music, and when a friend asked him to explain and demonstrate the creation of a stencil, he chose to use the banal image of Andre the Giant on a newspaper ad for the demonstration. Soon after that, Fairey introduced his pieces to the streets via Graffiti Art. Two of Fairey's well-known pieces are Obey (1992) and Hope (2008). Hope is an iconic portrait of the American president Barack Obama that Fairey produced during the 2008 American presidential campaign.
Fairey has been involved in both solo and group exhibitions; he has held solo exhibitions in Capsule, Birmingham, England (2000); Kantor Gallery Window, New York, NY (2003); and Merry Karnosky Gallery, Los Angeles, CA (2007). Examples of his group exhibitions include those at CPOP Gallery, Detroit, MI, (2001); Ducky Waddles Emporium, Encinitas, CA (2004); and OXOP Gallery, Minneapolis, MN (2006). Fairey received the Brit Insurance Design of the Year Award in 2009 for his Hope poster. He was commissioned by Time Magazine in 2011 to design a cover for the magazine. Fairey is represented by Irvine Contemporary gallery in Washington, DC. The artist lives and works in Los Angeles, CA.