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This statement may surprise some readers, but Lupe Fiasco is a pioneer in the footwear industry. Besides being an early endorser of skateboard fashion in hip-hop and pushing the boundaries of wordplay and metaphors, Fiasco has been on his sneaker business since before day one. As we look forward to Lupe’s performance at Fun Fun Fun Fest in Austin, TX, we take a look back at his innovative ventures in the sneaker industry.

photo via Lupe Fiasco

Since signing Swizzy, Reebok Classics has become arguably the most hip-hop savvy sneaker label in the biz. Before the recent reboot, RBK recruited a rap roster of young talent to enhance their endorsement in the music space. Lupe Fiasco joined a buzzing Lil Wayne and still tippin’ Mike Jones to back their OG model in campaigns.

Sure, many artists have shoe deals these days. Even before that, the likes of Run DMC, Jay Z and 50 Cent got sneaker money. What made Lupe’s deal so radical is that it came before he even had an album out. Following the success of the Fahrenheit 1st and 15th mixtape trilogy and preceding the release of his acclaimed Food & Liquor debut, his endorsement deal with Reebok was a low key breakthrough, and we’ve seen other brands and artists follow suit since.

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