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// Workers AI · dad joke modeWhat did "Chicago Freestyle" say to the map? You're always routing for me.

From Wikipedia, the free encyclopedia
"Chicago Freestyle"
Single by Drake and Giveon
from the album Dark Lane Demo Tapes
ReleasedMarch 1, 2020
Genre
Length3:40
LabelRepublic
Songwriters
Producer
  • Cadastre
Music video
"When To Say When" & "Chicago Freestyle" on YouTube

"Chicago Freestyle" is a song by Canadian rapper Drake and American singer-songwriter Giveon. It was released as the third track from Drake's commercial mixtape Dark Lane Demo Tapes, on May 1, 2020. Drake interpolates Eminem's flow from his 2002 single "Superman" on the pre-chorus.[1] When it was unofficially released on February 29, 2020, it was released concurrently with another song, "When to Say When".

Background

[edit]

On February 29, 2020, Drake released "When To Say When" and "Chicago Freestyle" on SoundCloud. He also released a music video for both songs.[2] The video stars Drake walking around New York City with scenes filmed in Marcy Projects in Brooklyn.[3] The song is set to a "romantic" piano and a "hushed" chorus performed by Giveon.[4] Lyrically, Drake "unpacks the run-of-the-mill anxieties and flexes" associated with his nightlife, while portraying "an underrated antagonist", as described by a Pitchfork article.[5]

Critical reception

[edit]

Grant Rindner of Complex felt that the lyrics reflected "Drake's first time being hurt in a long time", acknowledging "his heartbreak makes for great songs."[6] Kevin Montes of Medium deemed the song "one of the original standouts with its subtle melancholy vibe to Drake's reflection of celebrity life in his verses."[7] In a mixed review of both "Chicago Freestyle" and "When To Say When", Sheldon Pearce of Pitchfork felt Drake "doesn't play the heel nearly as well as '02 Em used to."[5] NME's Luke Morgan Britton found the song "cheesy."[8]

Charts

[edit]

Weekly charts

[edit]
Chart (2020) Peak
position
Austria (Ö3 Austria Top 40)[9]60
Canada Hot 100 (Billboard)[10]13
France (SNEP)[11] 62
Global 200 (Billboard)[12] 146
Ireland (IRMA)[13]9
Italy (FIMI)[14] 75
Lithuania (AGATA)[15] 54
Netherlands (Single Top 100)[16]75
New Zealand (Recorded Music NZ)[17] 31
Portugal (AFP)[18]38
Sweden Heatseeker (Sverigetopplistan)[19] 3
Switzerland (Schweizer Hitparade)[20]34
UK Singles (Official Charts)[21]10
US Billboard Hot 100[22]14
US Hot R&B/Hip-Hop Songs (Billboard)[23]11
US Rolling Stone Top 100[24] 6

Year-end charts

[edit]
Chart (2020) Position
US Hot R&B/Hip-Hop Songs (Billboard)[25] 65

Certifications

[edit]
Certifications for "Chicago Freestyle"
Region CertificationCertified units/sales
Australia (ARIA)[26] 3× Platinum 210,000‡
Brazil (Pro-Música Brasil)[27] Platinum 40,000‡
Denmark (IFPI Danmark)[28] Platinum 90,000‡
France (SNEP)[29] Gold 100,000‡
Italy (FIMI)[30] Gold 50,000‡
New Zealand (RMNZ)[31] 3× Platinum 90,000‡
Portugal (AFP)[32] Platinum 10,000‡
Spain (Promusicae)[33] Gold 30,000‡
United Kingdom (BPI)[34] Platinum 600,000‡
United States (RIAA)[35] 5× Platinum 5,000,000‡

‡ Sales+streaming figures based on certification alone.

References

[edit]
  1. ↑ "Every Song From Drake's Surprise Project, Ranked". Billboard. 2020-05-01. Retrieved 2020-05-01.
  2. ↑ "Drake's New Songs 'When to Say When' & 'Chicago Freestyle': See the Best Fan Reactions". Billboard.
  3. ↑ "First Impressions of Drake's New Songs "When to Say When" and "Chicago Freestyle"". Complex.
  4. ↑ "Drake Drops New Tracks 'When to Say When' and 'Chicago Freestyle': Listen". Billboard.
  5. 1 2 ""When to Say When"/ "Chicago Freestyle"". Pitchfork.
  6. ↑ "First Impressions of Drake's New Project Dark Lane Demo Tapes'". Complex. Retrieved 2020-05-02.
  7. ↑ Montes, Kevin (2020-05-03). "Drake — Dark Lane Demo Tapes: Review". Medium. Retrieved 2020-05-03.
  8. ↑ "Drake – 'Dark Lane Demo Tapes' review: business as usual on rapper's forgettable stop-gap release". NME. May 2020. Retrieved May 1, 2020.
  9. ↑ "Drake feat. Giveon – Chicago Freestyle" (in German). Ö3 Austria Top 40. Retrieved May 12, 2020.
  10. ↑ "Drake Chart History (Canadian Hot 100)". Billboard. Retrieved May 12, 2020.
  11. ↑ "Top Singles (Week 19, 2020)" (in French). Syndicat National de l'Édition Phonographique. Retrieved May 11, 2020.
  12. ↑ "Drake Chart History". Billboard. Retrieved September 15, 2020.
  13. ↑ "Official Irish Singles Chart on 8/5/2020 – Top 50". Official Charts Company. Retrieved May 8, 2020.
  14. ↑ "Top Singoli – Classifica settimanale WK 19" (in Italian). Federazione Industria Musicale Italiana. Retrieved May 8, 2020.
  15. ↑ "ALBUMŲ TOP100" (in Lithuanian). AGATA. May 8, 2020. Retrieved May 9, 2020.
  16. ↑ "Drake feat. Giveon – Chicago Freestyle" (in Dutch). Single Top 100. Retrieved May 8, 2020.
  17. ↑ "NZ Top 40 Singles Chart". Recorded Music NZ. May 11, 2020. Retrieved May 9, 2020.
  18. ↑ "Drake feat. Giveon – Chicago Freestyle". AFP Top 100 Singles. Retrieved May 15, 2020.
  19. ↑ "Veckolista Singlar, vecka 19". Sverigetopplistan. Retrieved May 8, 2020.
  20. ↑ "Drake feat. Giveon – Chicago Freestyle". Swiss Singles Chart. Retrieved May 10, 2020.
  21. ↑ "Official Singles Chart on 8/5/2020 – Top 100". Official Charts Company. Retrieved May 8, 2020.
  22. ↑ "Drake Chart History (Hot 100)". Billboard. Retrieved May 11, 2020.
  23. ↑ "Drake Chart History (Hot R&B/Hip-Hop Songs)". Billboard. Retrieved May 12, 2020.
  24. ↑ "Top 100 Songs, May 1, 2020 - May 7, 2020". Rolling Stone. Archived from the original on June 29, 2020. Retrieved May 7, 2020.
  25. ↑ "Hot R&B/Hip-Hop Songs – Year-End 2020". Billboard. Retrieved December 4, 2020.
  26. ↑ "ARIA Charts – Accreditations – 2024 Singles" (PDF). Australian Recording Industry Association. Retrieved October 25, 2025.
  27. ↑ "Brazilian single certifications – Drake – Chicago Freestyle" (in Portuguese). Pro-Música Brasil. Retrieved March 8, 2024.
  28. ↑ "Danish single certifications – Drake feat. Giveon – Chicago Freestyle". IFPI Danmark. Retrieved March 1, 2025.
  29. ↑ "French single certifications – Drake feat Giveon – Chicago Freestyle" (in French). SNEP. Retrieved October 3, 2023.
  30. ↑ "Italian single certifications – Drake feat. Giveon – Chicago Freestyle" (in Italian). Federazione Industria Musicale Italiana. Retrieved May 16, 2023.
  31. ↑ "New Zealand single certifications – Drake feat. Giveon – Chicago Freestyle". Radioscope. Retrieved October 25, 2025. Type Chicago Freestyle in the "Search:" field and press Enter.
  32. ↑ "Portuguese single certifications – Drake feat. Giveon – Chicago Freestyle" (PDF) (in Portuguese). Associação Fonográfica Portuguesa. Retrieved May 24, 2022.
  33. ↑ "Spanish single certifications – Drake / Giveon – Chicago Freestyle". El portal de Música. Productores de Música de España. Retrieved September 9, 2024.
  34. ↑ "British single certifications – Drake ft Giveon – Chicago Freestyle". British Phonographic Industry. Retrieved October 23, 2022. Select singles in the Formats field. Type Chicago Freestyle Drake ft Giveon in the "Search:" field.
  35. ↑ "American single certifications – Drake – Chicago Freestyle (ft. Giveon)". Recording Industry Association of America. Retrieved October 25, 2025.
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