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The 2020s File Feature

IMY2

IMY2 — Drake Featuring Kid Cudi Two Paths Cross in the Pandemic's Long Shadow The summer of 2021 carried a particular emotional weight. Eighteen months of di…

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Watch « IMY2 » — Drake Featuring Kid Cudi, 2021

01 The Story

IMY2 — Drake Featuring Kid Cudi

Two Paths Cross in the Pandemic's Long Shadow

The summer of 2021 carried a particular emotional weight. Eighteen months of disrupted normalcy had left popular culture hungry for music that acknowledged complexity, and two of the most psychologically candid voices in modern rap were already thinking along similar lines. Drake and Kid Cudi had operated in different corners of the hip-hop world for over a decade, their artistic approaches sharing certain melancholic frequencies while diverging sharply on matters of style and intent. IMY2 brought them together at a moment when both artists were processing themes of longing, distance, and the accumulated cost of absence.

Kid Cudi's influence on Drake has been acknowledged within the broader discourse around Drake's emotional openness as a rapper. Where Kid Cudi helped pioneer the model of male vulnerability in hip-hop, cataloging anxiety and loneliness in a way that gave permission to an entire generation of artists who followed, Drake absorbed and commercialized that permission, making introspective rap a genre-defining mode rather than an outlier. Their collaboration on IMY2 was therefore not just a pairing of two big names but a meeting of an influence and the influenced.

Certified Lover Boy and the Album Context

IMY2 appeared on Drake's sixth studio album, Certified Lover Boy, released in September 2021. The album was one of the most anticipated releases of that year, arriving after extensive public speculation about its content and after Drake had navigated a period of intense personal and professional scrutiny. The LP debuted at number one and generated an enormous number of charting singles simply through the breadth of its tracklist and the size of Drake's fanbase, which by 2021 was large enough to chart nearly any album track through streaming volume alone.

Kid Cudi, meanwhile, had been on his own complex artistic journey in the preceding years, releasing work through Passion, Pain and Demon Slayin' and Entergalactic that deepened his reputation as an artist committed to emotional authenticity even when critical reception was mixed. His appearance on IMY2 was welcomed by fans of both artists as an overdue intersection of two career arcs that had long seemed destined to cross more explicitly.

The Chart Moment

IMY2 debuted on the Billboard Hot 100 on September 18, 2021, at number 22, a strong initial placement that reflected both the album's blockbuster streaming performance and the specific enthusiasm around this collaboration. The following week it dropped to number 72 as the broader Certified Lover Boy tracking period settled and listeners' attention distributed across the album's many other tracks. Two weeks on the chart represents a brief but meaningful commercial presence, particularly given the fiercely competitive environment created by the album's own tracklist.

The challenge for any individual track on a Drake album release is precisely this: the sheer volume of charting content means that each individual song competes not only with the broader marketplace but with its own siblings. Certified Lover Boy placed more than 20 songs on the Hot 100 simultaneously in its debut week, a feat made possible by the streaming era's methodology for chart tabulation. In that context, landing at 22 with a collaborative deep cut was a genuine achievement.

Kid Cudi's Contribution

What Kid Cudi brings to IMY2 is tonally distinctive. His approach to melody in rap has always been somewhat unconventional, leaning into humming and melodic improvisation in ways that create texture rather than simply delivering lyrics. On this track, his presence shifts the emotional register, adding a rawness that contrasts productively with Drake's more polished delivery. The dynamic between the two performers creates something with more emotional range than either might have produced alone on this particular subject matter.

The title itself abbreviates "I Miss You Too," and the track is unambiguous about its emotional subject: the ache of distance from people and moments that once felt central. Given the context of its release during the extended pandemic recovery period, those themes arrived with particular force.

Longing Preserved in Sound

In the catalog of both artists, IMY2 occupies a specific niche: a collaborative statement of emotional openness between two of the artists most responsible for normalizing that openness in hip-hop. The approximately 7.5 million YouTube views it has accumulated reflect ongoing discovery by listeners drawn either to Drake's vast back catalog or to Kid Cudi's devoted fanbase, many of whom treat his collaborations as events worth seeking out regardless of context.

Press play and hear two architects of modern emotional rap meeting in the space they both, in different ways, helped create.

"IMY2" — Drake Featuring Kid Cudi's singular moment on the 2020s charts.

02 Song Meaning

IMY2 — Longing, Absence, and the Emotional Architecture of Drake and Kid Cudi's Collaboration

Missing as a Modern Condition

By the time IMY2 arrived in September 2021, the cultural conversation around longing and absence had been running at a high frequency for well over a year. The pandemic had forced physical separations that compressed and intensified emotional connections, making the simple experience of missing someone feel more acute and more politically charged than it had been for generations. Drake and Kid Cudi were drawing on emotional territory that listeners understood from recent personal experience, not as abstract sentiment but as daily lived reality.

The track's title reduces a deeply human feeling to an abbreviation, a choice that is itself culturally legible. The shortening of "I Miss You Too" into "IMY2" reflects the way digital communication has restructured emotional expression, compressing sentiment into formats suited for text messages and social media. The irony is that the song itself expands that compressed shorthand back into something fully felt, giving the abbreviation the weight it lacks when tapped out on a phone screen.

Kid Cudi's Emotional Framework

Kid Cudi built his early career on cataloging male emotional experience with unusual candor. His debut album from 2009 established the terms of his artistic project: interior states, anxiety, alienation, and longing treated not as weaknesses to be hidden but as subjects worthy of serious musical exploration. IMY2 draws directly on that framework, placing Cudi in a context where his established emotional register aligns precisely with the song's needs.

The track is not merely about missing a romantic partner, though that reading is available. It carries the broader sense of missing a version of life, or a version of the self, that felt more complete before some rupture. That interpretive openness is characteristic of the best work in both artists' catalogs: songs that begin from a specific emotional premise but expand to accommodate the listener's own experience of similar feelings.

Drake, Vulnerability, and Masculine Emotional Expression

Drake's role in reshaping the emotional expectations placed on male rappers is well documented in the critical discourse around his career. Beginning with So Far Gone and accelerating through his major label work, he made introspection and romantic feeling central rather than peripheral to his artistic identity. IMY2 represents a late-period reaffirmation of that commitment, a track where the commercial artist who has sold hundreds of millions of records is still genuinely engaging with the emotional material that drove him at the start.

The pairing with Kid Cudi matters here because Cudi preceded Drake in staking this particular emotional territory. Bringing him into the song is, among other things, an acknowledgment of creative lineage and artistic debt, a statement about where certain currents in modern rap came from.

The 2021 Cultural Context

September 2021 was a strange moment in popular culture. Vaccination rates had created an uneven reopening of social life, and the relief of reconnecting with people and places was complicated by eighteen months of accumulated grief and disorientation. A song about longing and reunion arrived into an emotional environment that had been primed by lived experience to receive it with unusual depth of feeling. Listeners were not just relating to the theme intellectually; many were actively navigating the specific emotional experiences the track describes.

The response to IMY2 within the Certified Lover Boy discourse reflected this. In an album that generated enormous amounts of conversation and debate, this track consistently drew responses from listeners for whom it had hit with particular personal force, a reaction that tells you something real about the emotional precision of its construction. Good collaborative records sometimes work precisely because the combination of voices creates something neither voice could access alone, and this track is a genuine example of that principle in practice.

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