In 2002, during an era where mainstream Hip-Hop appeared heavily saturated with gangsterism and hustler narratives, a preppy, middle-class, pink Polo shirt-rockin’ producer from the Chicago suburbs shocked the Rap game by signing to Jay-Z’s Roc-A-Fella Records at its pinnacle. While renowned for his distinctive, soulful production, Kanye West had a notoriously hard time being taken seriously as a rapper. Even his future “Big Brother” and longtime collaborator Jay was hesitant to give the artist his big break, worried that ‘Ye wouldn’t fit into the Roc’s roster. “We all grew up street guys who had to do whatever we had to do to get by,” Jay told Time in 2005. “Then there’s Kanye [West], who to my knowledge has never hustled a day in his life. I didn’t see how it could work.”

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His struggle to get a record deal, detailed on the song “Last Call” off his seminal 2004 debut The College Dropout, was truly a formative experience for the artist. Even ‘Ye, known for his controversial outbursts and unapologetic immodesty, has attributed his infamous ego to these early rejections, in the past: “Some say he arrogant, can y’all blame him? / It was straight embarrassing how y’all played him / Last year, shoppin’ my demo, I was tryin’ to shine / Every motherf*cker told me that I couldn’t rhyme / Now I could let these dream killers kill my self-esteem / Or use my arrogance as the steam to power my dreams.”

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Before “Last Call,” however, ‘Ye vented about his arduous come up on another, lesser-known alleged College Dropout-reject that never saw a proper release (besides a white label vinyl 12” in 2003 and some mixtape spots). Help from the Wu-Tang Clan’s Ol’ Dirty Bastard manifested on the hook, introduced ‘Ye at the top of the track and wrapped it up at the end. The multi-talented artist attempted to stake his claim as the self-described “first producer to rap better than the rappers” on “Keep The Receipt.”

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The verse-less O.D.B. feature, credited to Dirt McGirt (his final name change, and one of many throughout his career), was most likely added as a ploy to help legitimize the then-unconventional Chi-Town MC. Reportedly, Roc co-founder Dame Dash advocated for heavy features on ‘Ye’s debut from the label’s other signees. Fresh off a two-year prison bid, Ol’ Dirty had announced his Roc-A-Fella deal that same year. Who better to lend the producer-turned-rapper some street cred?

Ye’s commercial success arguably marked the end of an epoch in Hip-Hop, popularizing the “Backpack Rap” aesthetic, a label once considered the ultimate diss (even among Underground Hip-Hop heads). For some, his outselling 50 Cent in their 2007 battle for album sales signified the end of so-called Gangsta Rap’s mainstream dominance, changing the face of popular music. Before he would be accepted by the masses, however, between traditionally clashing styles of Hip-Hop, West had to “bridge the Gap like Banana Republic and Old Navy” (as claimed on “Last Call”). He did so with the help of O.G.’s like O.D.B.