About two years ago, Diggy Simmons caught the attention of pop culture and the rap world by releasing his breakthrough “Made You Look” freestyle video on the Internet. With that one video, he had surpassed the aspiring rap career of his older brother, appeared on magazine covers, and dropped numerous mixtapes, revealing that Rev Run’s kid had some serious talent. Now as he embarks on the debut of his solo album, Unexpected Arrival, Diggy reflects on the freestyle that started it all.
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Photo: Kellyann Petry