While Drake’s discography boasts chart-topping anthems and genre-defining hits, some gems occasionally slip through the cracks.

Chicago Freestyle, a track nestled amongst the surprises of his mixtape Dark Lane Demo Tapes, is a prime example.

Fans were left scratching their heads when this introspective masterpiece landed on a mixtape—a project typically reserved for throwaways and experimentations.

Chicago Freestyle defied expectations, showcasing a depth and artistry that would have fit seamlessly on any of Drake’s studio albums.

But Chicago Freestyle isn’t just a hauntingly beautiful song; it’s a masterclass in collaboration.

Drake’s signature flow weaves effortlessly through the track, punctuated by the soulful vocals of Giveon, a rising star at the time.

And for eagle-eared listeners, a special treat awaits: Drake throws in a subtle homage to another rap legend.

In the pre-chorus, he cleverly interpolates Eminem’s flow from his iconic 2002 single “Superman,” adding a layer of nostalgic charm to the modern sound.

Let’s delve deeper and dissect the magic that makes Chicago Freestyle such a captivating listen.

From Unofficial Release to Chart Success

The song’s journey began unofficially in February 2020 alongside “When To Say When.”

Accompanied by a music video showcasing Drake navigating New York City, Chicago Freestyle garnered immediate attention.

The official release in May 2020 cemented its place as a fan favourite, solidifying its position on the mixtape.

A Blend of Smooth Sounds and Deep Lyricism

The song’s sonic landscape is captivating. A melancholic piano melody sets the mood, perfectly complementing Giveon’s hushed and soulful chorus.

Drake’s verses, delivered with a laid-back yet introspective flow, seamlessly transition into the chorus, creating a cohesive narrative.

Chicago Freestyle Lyric Breakdown: A Look Inside Drake’s World

In the opening lines, Giveon sings of a rendezvous “by The Bean” (referencing Chicago’s Cloud Gate sculpture) at “two-thirty.”

The city itself becomes a character, with “thirty degrees, way too cold, so hold me tight” painting a picture of a chilly encounter tinged with desire.

The repeated line, “Will I see you at the show tonight?” underscores the yearning for intimacy amidst the whirlwind of Drake’s life.

This yearning for connection becomes a central theme, a stark contrast to the fleeting encounters Drake describes in his verses.

As Drake steps into the song, his verses, delivered with a laid-back yet introspective cadence, paint a picture of his fast-paced lifestyle: “Truck to the plane to the truck/Truck to the hotel lobby.”

He reflects on the transient nature of fame, constantly on the move, with fleeting connections made and broken in different cities.

Lines like, “Area code in my phone / What numbers do I still have?/Who do I know from the past?” highlight the disconnect he feels despite the abundance of contacts.

A Touch of Hip-Hop History

For those with a keen ear for hip-hop history, Chicago Freestyle offers a subtle homage. In the pre-chorus, Drake cleverly interpolates Eminem’s flow from his iconic 2002 single “Superman.”

This unexpected nod to a rap legend adds a layer of depth and nostalgia to the modern sound, demonstrating Drake’s ability to seamlessly blend past and present influences.

Drake and Giveon: A Collaboration That Works

The magic of Chicago Freestyle lies not just in its introspective lyrics and captivating soundscape, but also in the brilliant collaboration between Drake and Giveon.

Giveon’s smooth vocals perfectly complement Drake’s introspective verses.

The contrast between their styles creates a captivating tension, mirroring the push and pull between Drake’s desire for connection and his guarded nature.

Drake, Giveon Chicago Freestyle: A Track That Resonates

Chicago Freestyle resonates with listeners due to its relatable themes. The song explores the complexities of navigating fame, fleeting connections, and the yearning for true love.

Drake’s introspective lyrics and Giveon’s soulful vocals create a powerful combination that lingers long after the song ends.

Whether you’re a Drake fan or simply appreciate introspective music, Chicago Freestyle is a hidden gem waiting to be discovered.

Ready to Dive In? Listen to Drake and Giveon’s Chicago Freestyle and experience this captivating track for yourself.

You might just find yourself adding it to your favourite playlist on repeat.

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Chorus: Giveon
Two-thirty, baby, won’t you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is whenever I visit
Windy city, she blowin’ me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?

Verse 1: Drake
Ayy, truck to the plane to the truck
Truck to the hotel lobby
Me, I go through underground garages
Presidential suite on deposit
Elevator up to the room
Shower up and then we hit the club
Touch down, gotta see what’s up
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
‘Member when you let me in between
That was 2017
All good, Chubbs will look around
Find one that seem my type
That my dawg and he know what I like
He done found me plenty in my life
Problem is, I meet a girl tonight
Then I go and treat her too nice
Galleria credit card swipes
I don’t even know if she a wife

Pre-Chorus: Drake
But I do know one thing though
Women, they come they go
Saturday through Sunday, Monday
Monday through Sunday, yo
Maybe I’ll love you one day
Maybe we’ll someday grow
‘Til then, I’ll sit my drunk ass on that runway
On this one way

Chorus: Giveon
Two-thirty, baby, won’t you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is whenever I visit
Windy city, she blowin’ me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?

Verse 2: Drake
Jewelry in the safe on arrival
Pistol on J for survival
Lot of people gunnin’ for the title
Lot of people tryna take us viral
I’m just tryin’ to have a nice night though
Waiter brought the check for the meal
She said, “Babe, I think there was a typo”
Nah, girl, I got it, that’s light though
I could show you bigger things than that
It’s gon’ be a minute ’til I’m back
Let me give you images that last
AMEX had a limit in the past
I had plenty women in the past
I done plenty sinnin’ in the past
You don’t need to know, but you can ask
Stickin’ on your backstage pass
All access ’cause you bad
You could go wherever with that ass
Show to the shower to the truck
Truck to the club for the party
You go in first with your girls
‘Cause I don’t know who’s out there watchin’

Pre-Chorus: Drake
But I do know one thing though
Women, they come they go
Saturday through Sunday, Monday
Monday, Sunday, yo
Maybe I’ll love you one day
Maybe we’ll someday grow
‘Til then, I’ll sit my drunk ass on that runway
On this one way

Chorus: Giveon
Two-thirty, baby, won’t you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is whenever I visit
Windy city, she blowin’ me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?