Chicago Freestyle (feat. Giveon)

"Chicago Freestyle" is a contemplative and melancholic exploration of the paradox of Drake's life: immense fame and luxury juxtaposed with profound loneliness and an inability to form lasting romantic connections. The song contrasts the glamorous, fast-paced lifestyle of a global superstar with the internal desire for genuine intimacy. Drake reflects on the transient nature of his relationships, which are often fleeting and transactional, dictated by his tour schedule and constant movement. Giveon's soulful chorus establishes the setting in Chicago and a yearning for a connection, symbolized by the invitation to meet at "The Bean," a public and yet intimate request. However, the repeated question, "Will I see you at the show tonight?" grounds this potential romance in the temporary reality of his visit. Drake's verses detail his disillusionment; he cycles through past contacts, finds them unavailable, and resorts to having his crew find him a companion for the night. This process highlights a sense of emptiness and the bittersweet reality that while he can have anyone, he struggles to find someone who matters. The interpolation of Eminem's "Superman" serves as a cynical mantra—"women, they come they go"—that encapsulates his jaded perspective on love, even as he wistfully hopes for something more permanent someday. Ultimately, the song is a reflection on romantic discontent and the emotional cost of a life lived in the public eye, constantly on the move.

The song opens with Giveon's soulful and atmospheric chorus, setting a scene in Chicago. He proposes a late-night rendezvous at 2:30 AM by the iconic Cloud Gate sculpture, famously known as "The Bean." There's a sense of longing and anticipation, acknowledging the cold Chicago weather and the need for closeness. The repeated question, "Will I see you at the show tonight?" highlights the transient nature of the connection, tied to the fleeting presence of a performer in town for a single night.

Drake's first verse immediately establishes his high-profile, constantly moving lifestyle: "Truck to the plane to the truck / Truck to the hotel lobby." He navigates his world with a practiced detachment, using underground garages to avoid the public eye and settling into presidential suites. Upon arriving in a city, his first instinct is to reconnect with past romantic interests. He scrolls through his phone, a modern-day Rolodex of past encounters, only to find that time has moved on. One woman has a new partner, while another has changed her number. He reminisces about a specific encounter from 2017, a memory that now feels distant. Faced with this solitude, he relies on his friend, Chubbs, to find him companionship for the night. This leads to a moment of cynical reflection: he meets a new woman but worries he treats her "too nice," lavishing her with gifts without knowing anything meaningful about her, not even if she's married. This transactional and hollow nature of his interactions is a source of weary contemplation.

The pre-chorus, which interpolates Eminem's "Superman," serves as the philosophical core of Drake's verses. He lands on a jaded, yet resigned, conclusion: "Women, they come, they go." This cyclical, week-long pattern reinforces the impermanence of his relationships. Despite this cynicism, a flicker of hope remains in his admission, "Maybe I'll love you one day / Maybe we'll someday grow." For now, however, he remains in a state of arrested development, a "drunk ass on that runway," perpetually in transit and unable to form lasting bonds.

In his second verse, Drake delves deeper into the pressures and paranoia of his fame. He mentions keeping his jewelry in a safe upon arrival and carrying a pistol for survival, painting a picture of a life where he is constantly a target. He's aware that many are "gunnin' for the title" and trying to use him for viral moments. Amid this chaos, his desire is simple: "I'm just tryna have a nice night." A brief interaction with a date over a dinner check reveals his casual wealth; when she points out a potential typo in the bill, he dismisses it effortlessly, a flex that also highlights the financial disparity in his relationships. He promises grander experiences but acknowledges his imminent departure, asking for photos to remember her by—a digital substitute for a real connection. The verse concludes with a confession of past sins and the walls he's built, represented by the exclusive backstage pass, a symbol of the conditional access he grants to people in his life.

The song concludes by returning to Giveon's haunting chorus, reinforcing the central theme. The plea to meet at "The Bean" and the question of seeing her at the show are left unanswered, encapsulating the song's overarching mood of melancholic uncertainty and the profound loneliness that accompanies a life of constant motion and superficial connections. The cycle of arrival, fleeting interaction, and departure is destined to repeat, leaving a lingering feeling of unfulfilled longing.

"Chicago Freestyle" was officially released on May 1, 2020, as the third track on Drake's commercial mixtape, Dark Lane Demo Tapes. However, the song first appeared alongside "When to Say When" when Drake surprise-released them on SoundCloud and YouTube on February 29, 2020. The accompanying music video, directed by Theo Skudra, was also released at that time and featured visuals for both tracks.

The song was produced by Noel Cadastre and Sevn Thomas. Cadastre also served as the recording engineer, while Noah "40" Shebib handled mixing and Chris Athens mastered the track. The songwriting credits include Drake (Aubrey Graham), Giveon (Giveon Evans), Noel Cadastre, and Sevn Thomas (Rupert Thomas Jr.). Notably, due to an interpolation, Marshall Mathers (Eminem), Jeff Bass, and Steve King are also credited as songwriters, as the pre-chorus borrows lyrics and flow from Eminem's 2002 hit "Superman".

Giveon's involvement came about after a trip to Chicago where he was opening for singer Snoh Aalegra. The opening line of his chorus, "Two-thirty, baby, won't you meet me by The Bean?", was written about this experience and became his breakthrough moment. When the song first dropped, many listeners initially mistook Giveon's distinctive baritone voice for that of Sampha, a previous Drake collaborator, leading Giveon to clarify his involvement on social media.

The rhyme and rhythm of "Chicago Freestyle" are central to its laid-back, yet melancholic atmosphere. The song has a tempo of approximately 123 BPM and is set in a 4/4 time signature, typical for hip-hop tracks, providing a steady, head-nodding rhythm.

Drake's verses are characterized by a relaxed, conversational flow that often prioritizes narrative coherence over strict rhyme schemes, resembling a free verse style. He employs multi-syllable rhymes and internal rhymes to add complexity and musicality to his lines. For example, in the lines "Presidential suite on deposit / Elevator up to the room / Shower up and then we hit the club," the rhyming is loose, focusing more on the storytelling. However, he tightens the scheme in other sections, such as "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."

The most structured part is the pre-chorus, interpolated from Eminem's "Superman," which uses a consistent AABB-esque rhyme scheme: "go" (A) / "yo" (A) / "day" (B) / "grow" (B-slant) / "runway" (B) / "one way" (B). This section provides a catchy, memorable anchor between the freer verses and Giveon's melodic chorus. The interplay between Drake's rhythmic lyrical delivery and the sparse, piano-led beat creates a sense of space and introspection, allowing the emotional weight of the lyrics to land effectively.

"Chicago Freestyle" showcases a blend of musical and literary techniques that create its signature melancholic and introspective mood.

• Musical Arrangement: The song is built around a "dreamy" and "melancholic" piano melody, which sets a contemplative tone. This is paired with modern trap and R&B elements like hi-hats and 808s, creating a sonic landscape that feels both classic and contemporary. Giveon's "hushed" and soulful baritone vocals on the chorus provide a stark, emotive contrast to Drake's more rhythmic, laid-back delivery.
• Vocal Delivery: Drake employs a laid-back, conversational flow throughout his verses, making his reflections on fame and relationships feel personal and direct. His delivery is confident yet tinged with weariness, effectively conveying the song's emotional complexity. The contrast between Giveon's smooth singing and Drake's rap-talk style mirrors the song's central tension between longing for love and the harsh reality of his lifestyle.
• Interpolation: A key stylistic choice is the interpolation of Eminem's 2002 song "Superman." Drake adopts Eminem's flow and adapts the lyrics for the pre-chorus ("But I do know one thing though / Women they come they go"). This homage serves multiple purposes: it grounds the track in hip-hop history, adds a layer of nostalgia, and uses a well-known, cynical take on relationships to reinforce Drake's own feelings of disillusionment.
• Narrative Voice: The song is a first-person narrative that offers a vulnerable glimpse into Drake's psyche. He plays the role of a "run-of-the-mill" celebrity unpacking his anxieties, but also portrays himself as an "underrated antagonist" in his own love life. This introspective storytelling is a hallmark of Drake's work, allowing listeners to connect with the personal side of his global fame.

"Chicago Freestyle" was released to a generally positive reception, praised for its introspective lyrics, melancholic atmosphere, and the standout feature from then-rising artist Giveon. The song was part of the Dark Lane Demo Tapes mixtape, which debuted at number two on the Billboard 200 chart. "Chicago Freestyle" itself was a commercial success, peaking at number 10 on the UK Official Singles Chart and number 9 on the Official Irish Singles Chart.

The track is significant for introducing Giveon to a mainstream audience; his soulful chorus was widely acclaimed and many listeners initially mistook him for the more established artist Sampha. This feature is often cited as a major catalyst for Giveon's subsequent rise in the R&B scene.

A notable aspect of the song's cultural discussion was its interpolation of Eminem's 2002 hit "Superman." This creative choice was seen as a respectful nod to a hip-hop legend and sparked conversations about the art of sampling and interpolation, demonstrating Drake's ability to seamlessly blend influences from different eras of rap. The song's themes of fame, loneliness, and fleeting romance resonated deeply with fans, making it a standout track on the mixtape and a frequently discussed piece in Drake's discography for its vulnerability and introspective storytelling.

"Chicago Freestyle" is rich with symbolism and metaphors that illustrate the themes of fame, transience, and emotional isolation.

• The Runway: Drake's line, "'Til then, I'll sit my drunk ass on that runway / On this one way," is a powerful metaphor for his life being in a constant state of departure and transit. The "one way" nature of the runway suggests a life moving forward at a relentless pace without the chance to turn back or settle down, symbolizing his inability to escape the cycle of fame and fleeting encounters.
• The Bean (Cloud Gate): The request to meet at "The Bean" is symbolic. As a famous, reflective landmark, it represents a moment of clarity and a desire for real connection amidst the distorted reality of Drake's celebrity life. It's a public place, yet the proposed late-night meeting imbues it with a sense of intimacy and secrecy.
• The Windy City: The reference to Chicago as the "Windy City" is used literally and metaphorically. The line "Windy city, she blowin' me kisses" personifies the city as a lover, but like the wind, her affection is intangible and fleeting, mirroring the temporary nature of his relationships there.
• Underground Garages: Drake's mention of going through "underground garages" symbolizes the hidden, less glamorous side of his life and the lengths he must go to maintain privacy. It contrasts with the public-facing image of a superstar, highlighting a life lived partially in the shadows to escape constant scrutiny.
• Backstage Pass: The backstage pass mentioned at the end of the second verse symbolizes the conditional and limited access people have to his life. It represents a barrier between his public persona and his private self, granting physical proximity but not necessarily genuine intimacy.

The most significant recurring element in "Chicago Freestyle" is Giveon's chorus, which acts as the song's emotional and thematic anchor. The lines "Two-thirty, baby, won't you meet me by The Bean?" and "Will I see you at the show tonight?" are repeated multiple times. This repetition emphasizes the central theme of a fleeting, potential connection tied to a specific time and place. It highlights a sense of longing and uncertainty, as the question of whether the meeting will happen is left perpetually unanswered.

Another key recurring motif is the idea of transience and constant movement. This is introduced immediately in Drake's first verse with "Truck to the plane to the truck / Truck to the hotel lobby" and reinforced by the pre-chorus line, "I'll sit my drunk ass on that runway / On this one way." This motif paints a picture of a life lived in a perpetual state of arrival and departure, which serves as the primary reason for the instability in his personal relationships.

The pre-chorus, "But I do know one thing though / Women, they come they go," is a cynical refrain that Drake returns to as a defense mechanism. It's a recurring philosophical conclusion he reaches after recounting his romantic frustrations, serving as a stark, memorable summary of his jaded outlook.