Few lyrics are as emblematic of drill as “Fredo in the cut / That’s a scary sight,” from Chief Keef’s 2012 breakout hit “I Don’t Like.” Guest rapper Lil Reese delivers the blunt, menacing lines with a hint of playfulness—and all those characteristics apply to the man they’re about. “Fredo” is Chicago rapper Fredo Santana, born Derrick Coleman. He’s there in the “I Don’t Like” video, bouncing around an apartment shirtless along with most of the rest of Keef’s GBE crew. But Fredo hardly blends in: he shoots the camera a quick glower that can send shivers down your spine, and the cross tattoo between his eyebrows makes an instant impression. “Fredo stood out to me,” 50 Cent wrote in a memorial Instagram post on Sunday. “When he said he looked up to me, l wanted to work with him but we didn’t get the chance to do anything.”
Looking at Fredo’s catalog, it’s easy to see how many other rappers respected him. Chicago all-stars filled his mixtapes, of course (Keef, G Herbo, King Louie), but Fredo also pulled in verses from Atlanta royals Future and Gucci Mane (on 2013’s Fredo Kruger and 2015’s Ain’t No Money Like Trap Money Vol. 1, respectively), New York Diplomat Juelz Santana (Fredo Kruger), genre-blending Renaissance man Childish Gambino (2014’s Walking Legend), Baton Rouge veteran Kevin Gates (Ain’t No Money Like Trap Money Vol. 1), and Houston underground legend Z-Ro (2016’s Fredo Mafia), to name a few. As the rest of the pop world backed away from drill after 2012, rap continued to embrace Fredo. In 2013 Drake cast him as a villain in the video for “Hold On, We’re Going Home,” the biggest hit from Nothing Was the Same.
