Chicago Freestyle
Featuring Giveon
"Chicago Freestyle," first released February 29, 2020 on SoundCloud as part of the Dark Lane Demo Tapes rollout, is one of the more unusual cuts in Drake's late-2010s catalog. Per credits adapted from Tidal and BMI, it was produced by Drake's longtime OVO engineer Noel Cadastre, with Sevn Thomas as co-producer (Thomas also played the track's piano) — not, as sometimes misreported, by Noah "40" Shebib. It is built around a stripped-down, romantic piano figure, and Drake interpolates Eminem's flow from his 2002 single "Superman" on the pre-chorus, a clear nod to the early-2000s mainstream rap of his adolescence. Drake spends the song in conversational, half-sung mode, with lyrics widely read as an address to a romantic interest who has cooled on him. The standout moment is the soulful baritone hook from a then-unknown Giveon, whose appearance became his major-label breakout overnight and led directly to his 2020-2021 ascent. The combined "When to Say When"/"Chicago Freestyle" video, directed by Theo Skudra, was shot in New York City — including the Marcy Projects in Brooklyn — not in Chicago. The song is often cited as the cleanest example of Drake's mentor-mode A&R instincts.
Sources & verification
Citations below were matched specifically to "Chicago Freestyle" and Dark Lane Demo Tapes. Drake Universe catalogs songs by album placement, verified collaborators, producers, samples, and themes, and avoids unsupported lyric-level claims.
- Dark Lane Demo Tapes — WikipediaWikipedia · 2026-05-18 — Primary reference for full track-by-track producer credits (adapted from Tidal/BMI), features, samples/interpolations, release date (May 1, 2020), recording history, critical reception and chart performance. Source of the producer corrections replacing the fabricated 'Vinylz' placeholder on all 14 tracks.
- Chicago Freestyle — WikipediaWikipedia · 2026-05-18 — Verification for 'Chicago Freestyle': Noel Cadastre producer with Sevn Thomas co-producer (and piano) — correcting the prior '40' attribution; Eminem 'Superman' interpolation; Giveon feature/breakout; combined video shot in New York City (not Chicago); chart and certification data.
- Stories From the Making of Drake's 'Dark Lane Demo Tapes'Complex · 2026-05-18 — Producer-sourced making-of detail cited via Wikipedia: Plain Pat co-produced 'Deep Pockets' (originally a Scorpion cut) with 40; MexikoDro co-produced the 2017 plugg-music 'From Florida with Love' with 40; Foreign Teck on the secluded LA sessions that produced 'Gold Roses' and 'Losses'; Southside's 2017 origin of 'D4L'; JB Made It producing 'Demons.'
- Every Producer Who Worked on Drake's 'Dark Lane Demo Tapes'Variety · 2026-05-18 — Corroborating per-track producer roster (Shirley Ju, May 3, 2020), cross-referenced against the Tidal/BMI credits to confirm replacement of the fabricated 'Vinylz' placeholder.
