Lupe Fiasco

Before he was known for posting long-winded rants on social media, Chicago-native Lupe Fiasco was one of hip-hop’s most promising artists. Much like Kanye West’s The College Dropout or Kendrick Lamar’s Damn, Fiasco’s 2007 sophomore effort The Cool became an instant hip-hop classic, ahead of its time and regularly quoted by many of today’s leading rappers. Led by the infectious Billboard Top 10 hit “Superstar” featuring Matthew Santos, The Cool’s subject matter touched upon issues of race, class and police brutality, all the while appealing to white kids across the globe. Eleven years after the album’s release, Fiasco may no longer be hip-hop’s golden child (he’s touted as one of the genre’s greatest lyricists), but his early works and their enduring legacy remain intact.