Chicago Freestyle - Wikipedia

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• 1 Background
• 2 Critical reception
• 3 Charts Toggle Charts subsection
  • 3.1 Weekly charts
  • 3.2 Year-end charts
• 4 Certifications
• 5 References

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Appearance move to sidebar hide From Wikipedia, the free encyclopedia 2020 song by Drake and Giveon

"Chicago Freestyle"
Single by Drake and Giveon
from the album Dark Lane Demo Tapes
Released	March 1, 2020
Genre	Hip-hop R&B
Length	3:40
Label	Republic
Songwriters	Aubrey Graham Giveon Evans Rupert Thomas, Jr. Noel Cadastre Marshall Mathers Jeff Bass Steve King
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)	Peakposition
Austria (Ö3 Austria Top 40)[9]	60
Canada (Canadian Hot 100)[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 (OCC)[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	Certification	Certified 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. ^ a b ""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 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 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). Syndicat National de l'Édition Phonographique. 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.
35. ^ "American single certifications – Drake – Chicago Freestyle (ft. Giveon)". Recording Industry Association of America. Retrieved October 25, 2025.

v t e Drake songs
Singles discography
So Far Gone(Mixtape / EP)	"Successful" "November 18th" "Best I Ever Had" "I'm Goin' In"
We Are Young Money	"Every Girl" "BedRock"
Thank Me Later	"Fireworks" "Over" "Up All Night" "Fancy" "Miss Me" "Find Your Love" "9AM in Dallas"
Take Care	"Over My Dead Body" "Shot for Me" "Headlines" "Crew Love" "Take Care" "Marvins Room" "We'll Be Fine" "Make Me Proud" "HYFR (Hell Ya Fucking Right)" "The Motto"
Nothing Was the Same	"Tuscan Leather" "Furthest Thing" "Started from the Bottom" "Wu-Tang Forever" "Worst Behavior" "From Time" "Hold On, We're Going Home" "The Language" "Too Much" "Pound Cake / Paris Morton Music 2" "All Me"
If You're Reading ThisIt's Too Late	"Energy" "Preach"
What a Time to Be Alive	"Jumpman"
Views	"Controlla" "One Dance" "Pop Style" "Too Good" "Hotline Bling"
More Life	"Free Smoke" "No Long Talk" "Passionfruit" "Gyalchester" "Portland" "KMT" "Glow" "Fake Love" "Teenage Fever"
Scary Hours / Scorpion	"God's Plan" / "Diplomatic Immunity" "Survival" "Nonstop" "Elevate" "Emotionless" "I'm Upset" "8 Out of 10" "Mob Ties" "Can't Take a Joke" "Talk Up" "Jaded" "Nice for What" "That's How You Feel" "In My Feelings" "Don't Matter to Me"
Care Package	"Trust Issues" "Paris Morton Music"
Dark Lane Demo Tapes	"Chicago Freestyle" "Toosie Slide" "Time Flies" "Pain 1993" "War" "Desires"
Scary Hours 2	"What's Next" "Wants and Needs" "Lemon Pepper Freestyle"
Certified Lover Boy	"Champagne Poetry" "Papi's Home" "Girls Want Girls" "In the Bible" "Love All" "Fair Trade" "Way 2 Sexy" "TSU" "N 2 Deep" "No Friends in the Industry" "Knife Talk" "7AM on Bridle Path" "Race My Mind" "Fountains"
Honestly, Nevermind	"Falling Back" "Sticky" "Massive" "Jimmy Cooks"
Her Loss	"Rich Flex" "Major Distribution" "On BS" "BackOutsideBoyz" "Spin Bout U" "Circo Loco" "Pussy & Millions" "Jumbotron Shit Poppin"
For All the Dogs /Scary Hours Edition	"Virginia Beach" "Amen" "Calling for You" "Fear of Heights" "Daylight" "First Person Shooter" "IDGAF" "7969 Santa" "Slime You Out" "8AM in Charlotte" "Gently" "Rich Baby Daddy" "Evil Ways" "You Broke My Heart"
Drake–KendrickLamar feud	"Push Ups" "Taylor Made Freestyle" "Family Matters" "The Heart Part 6"
Some Sexy Songs 4 U	"CN Tower" "Gimme a Hug" "Nokia" "Die Trying" "Somebody Loves Me"
Iceman	"What Did I Miss?" "Which One" "Dog House"

v t e Giveon
Discography
Studio albums	Give or Take (2022) Beloved (2025)
EPs	Take Time (2020) When It's All Said and Done (2020)
Compilations	When It's All Said and Done... Take Time (2020)
Singles	"Heartbreak Anniversary" "For Tonight" "Lie Again" "Lost Me" "Twenties"
Featured singles	"Last Heartbreak Song" "Peaches" "Are You Even Real
Other songs	"Chicago Freestyle" "In the Bible"

Authority control databases	MusicBrainz release group

Retrieved from "https://en.wikipedia.org/w/index.php?title=Chicago_Freestyle&oldid=1318761306" Categories:

• 2020 songs
• Drake (musician) songs
• Giveon songs
• Songs written by Drake (musician)
• Songs written by Giveon
• Songs written by Eminem
• Songs written by Sevn Thomas
• Songs written by Jeff Bass

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• Single chart usages for Austria
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• Single chart usages for Billboardrandbhiphop
• Certification Table Entry usages for Australia
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