![]() ^ a b " "When to Say When"/ "Chicago Freestyle" ".^ "Drake Drops New Tracks 'When to Say When' and 'Chicago Freestyle': Listen".^ "First Impressions of Drake's New Songs "When to Say When" and "Chicago Freestyle" ".^ "Drake's New Songs 'When to Say When' & 'Chicago Freestyle': See the Best Fan Reactions".^ "Every Song From Drake's Surprise Project, Ranked".Sales+streaming figures based on certification alone. ![]() 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." 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." 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." NME 's Luke Morgan Britton found the song "cheesy." Charts Weekly charts Chart (2020) 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. The song is set to a "romantic" piano and a "hushed" chorus performed by Giveon. The video stars Drake walking around New York City with scenes filmed in Marcy Projects in Brooklyn. He also released a music video for both songs. On February 29, 2020, Drake released "When To Say When" and "Chicago Freestyle" on SoundCloud. When it was unofficially released on February 29, 2020, it was released concurrently with another song, "When to Say When". Drake interpolates Eminem's flow from his 2002 single " Superman" on the pre-chorus. It was released as the third track from Drake's commercial mixtape Dark Lane Demo Tapes, on May 1, 2020. " Chicago Freestyle" is a song by Canadian rapper Drake and American singer-songwriter Giveon. "When To Say When" & "Chicago Freestyle" on YouTube 2020 song by Drake and Giveon "Chicago Freestyle"
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