"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 &lt;a href="Grammy%20Award%20for%20Best%20Rap/Sung%20Collaboration"&gt;Best Rap/Sung Collaboration&lt;/a&gt;. The music video, featuring a variety of celebrity guests, earned a Video Music Award nomination for Best UK Video. Estelle and West performed the song at the 2008 MTV Europe Music Awards and 2008 Grammy Awards. "American Boy" was featured in the 2009 film "Obsessed".