" American Boy " was released by Atlantic Records as the album 's second single on 31 March 2008 . The song received positive reviews from music critics , who praised its fresh sound and production . The song reached the top five in many European and Oceanic markets , and peaked at number-one in Belgium and Estelle 's native United Kingdom . It also achieved success in the United States , peaking at number nine on the Billboard Hot 100 and becoming Estelle 's breakout song in the country . The song earned many nominations , and ultimately won a Grammy Award for Best Rap/Sung Collaboration . The music video , featuring a variety of celebrity guests , earned a Video Music Award nomination for Best UK Video . As a result of the song 's popularity , Estelle performed it at several award shows and venues
Video Music Award
2008 MTV Video Music Awards
American Boy