On the latest episode of The Need to Know Podcast, hip-hop journalist Elliot Wilson addressed one of the most talked-about dynamics in hip-hop—his complicated relationship with Drake. In a candid conversation, Wilson reflected on the fallout between him and the Canadian rapper, acknowledging how his actions in 2020 may have contributed to their distance, and how repairing their relationship could require a major shift in both his personal and professional life.
Wilson began by acknowledging the severity of the rift, saying that some may view repairing the relationship as “damn near impossible.” The conversation touched on the tension created when Wilson moved from the East Coast to the West, as well as his involvement in pivotal moments of hip-hop beefs—specifically, his role during the infamous Kendrick Lamar and Drake showdown. As Wilson himself puts it, “I think I would have to go on a Kendrick Lamar-like run,” to prove himself worthy of regaining Drake’s respect.
“To earn his respect outside of whatever feelings he may have about what happened… I think I have to show I’m back in the conversation,” Wilson said, referencing the time when his influence in hip-hop media was at its peak. For Wilson, it’s not just about mending fences—it’s about proving his value in an evolving landscape where media narratives and the relationship between journalists and artists are under constant scrutiny.
He continued, explaining that regaining Drake’s respect wouldn’t happen overnight. Instead, it would require him to show through his actions that he’s evolved, with a content-driven, Kendrick Lamar-esque run to demonstrate his relevance. “It’s not direct… He’s gonna have to see it for himself first,” Wilson admitted. “Then, he might be willing to say, ‘Let’s sit down and see if we could have a conversation.'”
This delicate balance between media commentary and artist relationships surfaced as Wilson dissected how his previous actions were perceived by the public. He elaborated on how fans and critics alike misinterpreted his stances, citing how his love for certain artists like Kendrick Lamar led to backlash from loyal Drake supporters. “I love music…What the hell is wrong with you?!” Wilson said, recalling how he was even called a hypocrite for liking Kendrick’s music while navigating the public discourse around the Drake/Kendrick rivalry.
However, the conversation wasn’t all introspection. Wilson also shed light on the larger hip-hop culture, examining why he believes that the “battle” between Drake and Kendrick Lamar was so crucial. He talked about how Kendrick’s unexpected rise with Control shocked the hip-hop world, creating a ripple effect in the rap scene. “I think Kendrick surprised everybody. We knew he was the Boogie, but we never saw him rumble,” Wilson explained. “Kendrick performed differently, and we were all shocked.”
Yet, while the Kendrick/Drake rivalry certainly shaped their respective careers, Wilson admitted to being disappointed by some of Drake’s moves after that pivotal moment. “I think he underestimated Kendrick… tried to little bro him… and it just didn’t work,” Wilson said, expressing his frustrations over Drake’s refusal to acknowledge Kendrick’s growth.
Still, Wilson remains hopeful about the future. Despite acknowledging the immense difficulty in repairing the fractured relationship, he is committed to proving himself through consistent work and a deeper understanding of the evolving culture.
“I think Drake realizes that everybody feels he lost, but in his mind, the numbers are the ultimate victory,” Wilson concluded. “In the end, it’s a battle of perception versus reality.”
