Checkoway has a lauded career as a journalist known for her ability to weave contemporary social issues through the stories of personalities. Raised on poetry and hip-hop, her cinematic storytelling leapt off the page; her attention to detail and interest in psychology creates vivid insightful portraits of the era’s most beloved artists and superstars. Some of her notable stories include travelling throughout Nigeria with Jay-Z, Mary J. Blige, Chris Brown, and Rihanna; celebrating blues legend B.B. King’s birthday with him in his Mississippi Delta hometown; chronicling singer Solange's rise to stardom in the shadows of her famous sister Beyonce.