"Chicago Freestyle" is a song by Canadian rapper

Drake Drake may refer to: Animals * A male duck People and fictional characters * Drake (surname), a list of people and fictional characters with the family name * Drake (given name), a list of people and fictional characters with the given name * ...

and American singer-songwriter

Giveon Giveon Dezmann Evans (born February 21, 1995), better known by his mononym Giveon (stylized as GIVĒON), is an American singer-songwriter. He rose to prominence with his collaboration with Drake on their 2020 single, "Chicago Freestyle". That sa ...

. It was released as the third track from Drake's commercial mixtape ''

Dark Lane Demo Tapes ''Dark Lane Demo Tapes'' is a mixtape by Canadian rapper and singer Drake. The mixtape is a compilation of songs that were released on SoundCloud or leaked on the internet, as well as new songs, and is considered a "warm-up" to Drake's sixth stu ...

'', on May 1, 2020. Drake interpolates

Eminem Marshall Bruce Mathers III (born October 17, 1972), known professionally as Eminem (; often stylized as EMINƎM), is an American rapper and record producer. He is credited with popularizing hip hop in middle America and is critically acclai ...

's flow from his 2002 single "

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" on the pre-chorus. When it was unofficially released on February 29, 2020, it was released concurrently with another song, "When to Say When".

Background

On February 29, 2020, Drake released "When To Say When" and "Chicago Freestyle" on

SoundCloud SoundCloud is an online audio distribution platform and music sharing website that enables its users to upload, promote, and share audio. Founded in 2007 by Alexander Ljung and Eric Wahlforss, SoundCloud is one of the largest music streaming se ...

. He also released a music video for both songs. The video stars Drake walking around New York City with scenes filmed in Marcy Projects in Brooklyn. The song is set to a "romantic" piano and a "hushed" chorus performed by Giveon. Lyrically, Drake "unpacks the run-of-the-mill anxieties and flexes" associated with his nightlife, while portraying "an underrated antagonist", as described by a ''

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'' article.

Critical reception

Grant Rindner of ''

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'' felt that the lyrics reflected "Drake's first time being hurt in a long time", acknowledging "his heartbreak makes for great songs." Kevin Montes of

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deemed the song "one of the original standouts with its subtle melancholy vibe to Drake's reflection of celebrity life in his verses." In a mixed review of both "Chicago Freestyle" and "When To Say When", Sheldon Pearce of ''

'' felt Drake "doesn't play the heel nearly as well as '02 Em used to." ''

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''s Luke Morgan Britton found the song "cheesy."

Charts

Weekly charts

Year-end charts

Certifications

References

{{authority control 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