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Drake Surprises with "When To Say When" & "Chicago Freestyle"

Mahlik Campbell

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Christopher Polk via Getty Images

Drizzy unveiled two surprise tracks over the weekend, "When To Say When" and "Chicago Freestyle."

In doing so, he officially clears the air about why he was shooting a video in front of Marcy Houses in Brooklyn a few weeks ago. Marcy is most known for being the housing complex where Jay-Z grew up.

There was plenty of speculation about what Drake was doing in Jay's old hood, especially since the two have traded competitive jabs before.

In the original clip that surfaced, Drake appears to be distracted and possibly nervous as he looks over his shoulder several times. He then addressed his behavior after some viewers were trying to clown him, saying he looked shook. Stop with the hate!

https://twitter.com/ThaYnoe/status/1226653492804112385

https://www.instagram.com/p/B8XjZB7j9_J/?utm_source=ig_embed

It makes sense the Six God was in Brooklyn to shoot a scene for "When To Say When" as it samples a few elements from Jay-Z's 2001 single "Song Cry."

In addition to reciting lyrics about trust issues and dapping up a few local residents outside of Marcy Houses, the video finds Drake copping some jewelry from Jacob & Co in the Diamond District and trying to stay warm while donning a couple of Jesus pieces in front of the Manhattan Bridge. Drake recently commissioned Jacob & Co. to design a masterpiece of a watch that includes a mini roulette table in place of the watch dial.

Once the video quickly transitions to "Chicago Freestyle" at the 2:22 mark (possibly another hint at the Jay-Z influence, as his last album was titled 4:44), we see an owl, the mascot for Drake's OVO brand, pop up in place of the Rolls-Royce Spirit of Ecstasy hood ornament.

Guided by a lo-fi beat, Drake reflects on casual communications with women in various cities, "Area code in my phone / What numbers do I still have? / Who do I know from the past? / Hit one, she say she got a man / Hit another one, it goes green / Must've changed phones on the team." 

https://twitter.com/J_batacao/status/1234169785627398144

Later, Drake pays homage to Eminem and his song "Superman," imitating the flow and words that Em employs on its hook. Drake raps, "But I do know one thing though / Women they come they go / Saturday, through Sunday, Monday / Monday through Sunday, yo."

Stream both songs in full on SoundCloud and see some of our favorite fan interpretations below.

https://soundcloud.com/octobersveryown/drake-when-to-say-when

https://soundcloud.com/octobersveryown/drake-chicago-freestyle

https://twitter.com/GoodNightHarlem/status/1233993424078020608

https://twitter.com/countmagic/status/1234002275670073346

https://twitter.com/ItsPaoloni/status/1234160055865376768

https://twitter.com/Zames231/status/1234109366292373505

https://twitter.com/norfdog/status/1234207836843974661