K’naan became a friend and associate of Canadian promoter Sol Guy, who helped him secure a speaking engagement before the United Nations High Commissioner for Refugees in 1999, where K’naan performed a spoken word piece criticizing the UN for its failed aid missions to Somalia. One of the audience members, Senegalese singer Youssou N’Dour, was so impressed by the young MC’s performance and courage that he invited him to contribute to his 2001 album Building Bridges, a project through which K’naan was able to tour the world.
This project led to his work at other UN events, as well as the Montreal Jazz Festival and the Halifax Pop Explosion. It also helped him meet Canadian producer Brian West and Jarvis Church and his Track & Field team in 2002, who produced his debut album The Dusty Foot Philosopher, which was released in 2005 to critical acclaim. In 2006, it won the Juno Award for Rap Recording of the Year, and was nominated for the 2006 Polaris Music Prize. It also won the BBC Radio 3 Award for World Music in the newcomer category for 2007. The Dusty Foot Philosopher was re-released and re-packaged as a “Deluxe Edition” featuring new mixes and a bonus DVD in the United States (and various international territories) by the emerging media company and record label iM (Interdependent Media, Inc.) in 2008.
Since then, K’naan had been on tour promoting his album and working on his follow-up release, Troubadour, which he released in the summer of 2010. It was his debut album for new label, A&M/Octone Records. He has also collaborated with artists like Nelly Furtado, Mos Def, Will.i.am, The Roots, Dead Prez, and Pharoahe Monch on tours such as Live 8 and Breedlove Odyssey. He also collaborated with Damian Marley on the “Welcome to Jamrock” touring session.
K’naan released The Dusty Foot on the Road, a collection of recording made during his world tour on Wrasse Records.
K’naan rose to mainstream popularity by participating in the 2008 BET Awards Cypher. This was his first appearance on American television. His second studio album, Troubadour, was released on 24 February 2009 on A&M/Octone Records, and will be distributed through Universal Music Group worldwide. The album’s first single, “ABC’s”, was released to radio in late 2008. K’naan’s music has featured in several video games such as Madden NFL 09 (with his song “ABC’s”) and FIFA 06 (with his song “Soobax”). The song “If Rap Gets Jealous”, a re-recording of a track of the same name – with different verses – from The Dusty Foot Philosopher, features Metallica lead guitarist Kirk Hammett. K’naan was also the first featured artist on X3, a collaborative project between CBC Radio 3, Exclaim! magazine and aux.tv to promote new Canadian music. In July 2010, he performed a cover of U2′s “Stuck in a Moment You Can’t Get Out Of” for iheartradio.
A remixed version of K’naan’s single, “Wavin’ Flag,” was chosen as Coca-Cola’s anthem for the 2010 FIFA World Cup. It was also used in the commercials for the pre-game, which was held in South Africa. Additionally, the track is in the soundtrack for the official EA Sports 2010 FIFA World Cup video game. In December 2009, K’naan performed the song live during the sponsor’s FIFA World Cup Trophy Tour, which took him to 86 countries around the world. His performance of “Wavin’ Flag” was featured in the Top 10 hits in 11 different countries across the world. This also included number one hits in Mexico, Austria, China, Germany, Luxembourg, and Switzerland. In order to appeal to different people around the world, K’naan has also recorded the song with various local artists such as David Bisbal, Jacky Cheung, Jane Zhang, and Tattoo Colour.