Chicago Freestyle

Featuring Giveon

Chicago Freestyle, released in February 2020 as part of the Dark Lane Demo Tapes rollout, is one of the more unusual cuts in Drake's late-2010s catalog. Produced by Noah '40' Shebib, the track is built around a deliberately stripped-down piano loop that interpolates Eminem's 'Superman' from The Eminem Show — a clear nod to the early-2000s mainstream rap that shaped Drake's adolescence. Drake spends the song in conversational, half-sung mode, with lyrics widely read as a long-distance address to a romantic interest who's no longer responding the way she used to. The standout moment is the soulful, baritone hook from a then-unknown Giveon, whose appearance on the track became his major-label breakout overnight and led directly to his 2020-2021 ascent. The accompanying video, directed by Theo Skudra, was filmed during what looked like a quiet Chicago winter and emphasized the song's intimate, conversational tone. Chicago Freestyle is often cited as the song that introduced Giveon to a mainstream pop audience and one of the cleanest examples of Drake's mentor-mode A&R instincts.