Claim: Live Your Life was a single.

`` Live Your Life '' is a song by American rapper T.I. , from his sixth studio album , Paper Trail -LRB- 2008 -RRB- , and features Barbadian singer Rihanna . It was released as the seventh single from the album on September 23 , 2008 . The song is a conscious hip hop track with elements of contemporary R&B . The song 's lyrics speak of T.I. 's rise to fame and optimism of the future . It also gives dedication to the American troops fighting in Iraq and Afghanistan .   `` Live Your Life '' was a commercial success worldwide . In the United States , the song topped the Billboard Hot 100 , marking T.I. 's third number-one single , and Rihanna 's fifth . The song also attained top ten placements in twelve other countries , reaching the top five in Australia , Canada , the Netherlands , New Zealand and the United Kingdom . Furthermore , `` Live Your Life '' topped the US Mainstream Top 40 and Rap Songs charts and reached number two on the Hot R&B / Hip-Hop Songs chart . The song remains T.I. 's highest charting and most successful single worldwide since its release .   The song 's accompanying music video , directed by Anthony Mandler , depicts a story of T.I. 's rise to fame in a narrated form , featuring Rihanna performing in a dressing room and bar . The duo performed `` Live Your Life '' at the 2008 MTV Video Music Awards . The song is featured in the 2009 film The Hangover as well as the trailer .