Chicago Freestyle

"Chicago Freestyle" is a song by Canadian rapper Drake from his commercial mixtape Dark Lane Demo Tapes (2020). It features guest vocals by American singer Giveon. Drake interpolates Eminem's flow from his 2002 single "Superman" on the pre-chorus.[2] It was released concurrently with another song, "When To Say When".

"Chicago Freestyle"
Single by Drake featuring Giveon
from the album Dark Lane Demo Tapes
ReleasedMay 8, 2020 (2020-05-08)[1]
Length3:40
Label
Songwriter(s)
Producer(s)
Drake singles chronology
"Toosie Slide"
(2020)		 "Chicago Freestyle"
(2020)		 "Greece" / "Popstar"
(2020)
Giveon singles chronology
"Heartbreak Anniversary"
(2020)		 "Chicago Freestyle"
(2020)		 "Ah Ah Ah"
(2020)
Music video
"When To Say When" & "Chicago Freestyle" on YouTube

Background

On February 29, 2020, Drake released "When To Say When" and "Chicago Freestyle" on SoundCloud. He also released a music video for both songs.[3] The video stars Drake walking around New York City with scenes filmed in Marcy Projects in Brooklyn.[4]

The song is set to a "romantic" piano and a "hushed" chorus performed by American singer Giveon.[5] 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.[6]

Critical reception

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."[7] 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."[8] 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."[6] NME's Luke Morgan Britton found the song "cheesy."[9]

Charts

Weekly charts
Chart (2020) Peak
position
Austria (Ö3 Austria Top 40)[10] 60
Canada (Canadian Hot 100)[11] 13
France (SNEP)[12] 62
Global 200 (Billboard)[13] 146
Ireland (IRMA)[14] 9
Italy (FIMI)[15] 75
Lithuania (AGATA)[16] 54
Netherlands (Single Top 100)[17] 75
New Zealand (Recorded Music NZ)[18] 31
Portugal (AFP)[19] 38
Sweden Heatseeker (Sverigetopplistan)[20] 3
Switzerland (Schweizer Hitparade)[21] 34
UK Singles (OCC)[22] 10
US Billboard Hot 100[23] 14
US Hot R&B/Hip-Hop Songs (Billboard)[24] 11
US Rolling Stone Top 100[25] 6

Year-end charts
Chart (2020) Position
US Hot R&B/Hip-Hop Songs (Billboard)[26] 65

Certifications
Region CertificationCertified units/sales
United Kingdom (BPI)[27] Silver 200,000

Sales+streaming figures based on certification alone.

Release history
Region Date Format Label Ref.
United Kingdom May 8, 2020 Rhythmic contemporary radio
  • OVO
  • Republic
 [1]

References
  1. "BBC – Radio 1Xtra – Playlist". BBC Radio 1Xtra. British Broadcasting Corporation. Archived from the original on May 14, 2020. Retrieved May 8, 2020.
  2. "Every Song From Drake's Surprise Project, Ranked". Billboard. 2020-05-01. Retrieved 2020-05-01.
  3. "Drake's New Songs 'When to Say When' & 'Chicago Freestyle': See the Best Fan Reactions". Billboard.
  4. "First Impressions of Drake's New Songs "When to Say When" and "Chicago Freestyle"". Complex.
  5. "Drake Drops New Tracks 'When to Say When' and 'Chicago Freestyle': Listen". Billboard.
  6. ""When to Say When"/ "Chicago Freestyle"". Pitchfork.
  7. "First Impressions of Drake's New Project Dark Lane Demo Tapes'". Complex. Retrieved 2020-05-02.
  8. Montes, Kevin (2020-05-03). "Drake — Dark Lane Demo Tapes: Review". Medium. Retrieved 2020-05-03.
  9. "Drake – 'Dark Lane Demo Tapes' review: business as usual on rapper's forgettable stop-gap release". NME. Retrieved May 1, 2020.
  10. "Austriancharts.at – Drake feat. Giveon – Chicago Freestyle" (in German). Ö3 Austria Top 40. Retrieved May 12, 2020.
  11. "Drake Chart History (Canadian Hot 100)". Billboard. Retrieved May 12, 2020.
  12. "Top Singles (Week 19, 2020)" (in French). Syndicat National de l'Édition Phonographique. Retrieved May 11, 2020.
  13. "Drake Chart History". Billboard. Retrieved September 15, 2020.
  14. "Official Irish Singles Chart Top 50". Official Charts Company. Retrieved May 8, 2020.
  15. "Top Singoli – Classifica settimanale WK 19" (in Italian). Federazione Industria Musicale Italiana. Retrieved May 8, 2020.
  16. "ALBUMŲ TOP100" (in Lithuanian). AGATA. May 8, 2020. Retrieved May 9, 2020.
  17. "Dutchcharts.nl – {{{artist}}} – {{{song}}}" (in Dutch). Single Top 100. Retrieved May 8, 2020.
  18. "NZ Top 40 Singles Chart". Recorded Music NZ. May 11, 2020. Retrieved May 9, 2020.
  19. "Portuguesecharts.com – Drake feat. Giveon – Chicago Freestyle". AFP Top 100 Singles. Retrieved May 15, 2020.
  20. "Veckolista Singlar, vecka 19". Sverigetopplistan. Retrieved May 8, 2020.
  21. "Swisscharts.com – Drake feat. Giveon – Chicago Freestyle". Swiss Singles Chart. Retrieved May 10, 2020.
  22. "Official Singles Chart Top 100". Official Charts Company. Retrieved May 8, 2020.
  23. "Drake Chart History (Hot 100)". Billboard. Retrieved May 11, 2020.
  24. "Drake Chart History (Hot R&B/Hip-Hop Songs)". Billboard. Retrieved May 12, 2020.
  25. "Top 100 Songs, May 1, 2020 - May 7, 2020". Rolling Stone. Retrieved May 7, 2020.
  26. "Hot R&B/Hip-Hop Songs – Year-End 2020". Billboard. Retrieved December 4, 2020.
  27. "British single certifications – Drake Ft Giveon – Chicago Freestyle". British Phonographic Industry. Retrieved August 23, 2020.
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