Although most of the national attention came in the wake of 2008's Mixtape About Nothing, Wale had been running around the mixtape circuit in D.C. for three years at that point, dropping his first in 2005. Paint A Picture and 2006's Hate Is The New Love both failed to blow up, but they introduced Wale as an ambitious, highly skilled MC, especially on his two-part "A.D.D." series. These marathon-length tracks had him taking on a bevy of eclectic beats, switching his flow accordingly and rarely even pausing to catch his breath. Here's part two, from Hate Is The New Love:
By 2007, he had made two key connections in the music world. The first was superproducer and London native Mark Ronson, who signed him to his Allido Records label in 2006; the second was DJ and (at the time) Fader editor Nick Catchdubs, who went on to mix Wale's two most successful tapes. The first of these was 2007's 100 Miles & Running, its title inspired by an N.W.A. EP, and it featured a mix of freestyles and tracks that still bore the influence of D.C.'s go-go scene. The other artists' tracks that he chose to jump on were notable for their stylistic breadth, with instrumentals from conscious rappers like Common, The Roots and Q-Tip butting up against those from indie acts like Gorillaz, Justice and Lily Allen. This helped Wale establish some hype in critical circles, getting featured on MTV and in The Washington Post soon thereafter, and having XXL call him "the thinking man's Lil Wayne." One of the tape's standout tracks, the go-go-ish "Breakdown," was even featured on the soundtrack of Madden NFL 09.
Just under a year later, The Mixtape About Nothing dropped. Lauded for its unique concept, witty lyrics and blend of humor and socially-conscious subject matter, the tape marks Wale's true breakout moment. His production team Best Kept Secret, who'd also produced most of 100 Miles, were on-board again, and they kept the freestyles to a minimum this time around, instead opting for tracks that melded classic-sounding samples (many taken from Seinfeld) with go-go's live drums. Lyrically, this might be the best we've ever heard Wale, as he deftly addresses issues that were important to the day and age (such as illegal downloading, ringtone rap, mixtape cliches and Seinfeld actor Michael Richards' racist rant) without ever sounding too preachy. Self-aware, clever and funny, Wale rapped "Hip-hop heads see a new day, and I is one" on the tape, and it was hard to disagree with him at that point.