Tonight @ Miller Lite Oasis, Summerfest, 10 p.m.
With vices off limits, though, he had plenty of time to rap about more personal topics on his 2006 debut Food and Liquor, like absentee fathers, daily life in Chicago (in both the suburbs and the streets) and, most prominently, his love of skateboarding. His feel-good ode to the sport, “Kick, Push,” became one of the defining singles of that summer, establishing Lupe as a bona fide star even before his first album was released.
Instead of being pigeonholed as the skateboarding rapper, however, Lupe revealed himself to be more ambitious than anyone could have expected on his 2007 sophomore album, Lupe Fiasco’s The Cool. The record is written around a mythology nearly as dense as the Lord of the Rings trilogy, and though it’s thematically confounding, it’s packed with triumphant arrangements and oversized pop hooks that complement Lupe’s slippery, focused storytelling, but its pop sheen is offset by a dark undercurrent unlike little else in hip-hop.