Kendrick Lamar & Collaborators Revisit The Darkest Moment In His Career

Art and music connoisseurs have crafted countless thinkpieces, articles, and dissertations attempting to uncover the depths of Kendrick Lamar’s To Pimp A Butterfly. Spotify’s The Big Hit Show was gifted the honor of conversing with the legendary musicians responsible for the album’s conception, offering a glimpse into the nearly immeasurable layers the project has to offer.


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On February 16th, The Big Hit Show released an episode titled “Hello Kendrick” – a nearly hour long explication of the inner workings of Kendrick Lamar’s mind prior to recording and releasing TPAB. A multitude of perspectives were present throughout, as collaborators and longtime friends detailed the nature of this creation. While the numerous sonic inspirations were illuminated through in-depth analysis, a single focal point of the documentation stood out: the dark, vast emptiness that comes with becoming a star.

Alex Pappademas, host of The Big Hit Show, shifted the core of the conversation from Kendrick reaching his zenith with the track “King Kunta,” to the internal turmoil, plaguing and eating away at him in the harrowing piece titled “U”:

To Pimp a Butterfly is musically fearless– the work of somebody who’s as fired-up creatively as he’s ever been. But on an even deeper level it’s a work born from a place of crisis and confusion. It’s Kendrick wrestling with temptation and survivors’ guilt and the knowledge that people want something more from the best rapper alive than just raps.”

Pappademas went on to introduce the song in summation, before many of Kendrick’s collaborators began peeling the bandages from the stitched, yet still very much open wound. “In a series of interludes on this album Kendrick reads a poem that mentions waking up screaming in a hotel room. In 2015 he confirmed to NPR that this really happened. ‘The feeling was… How am I influencing so many people on this stage rather than influencing the ones that I have back home?'”

Audibly revisiting the site of the proverbial war was Dave Free, Kendrick’s longtime manager and brother in arms. Citing survivor’s guilt as the perpetually lingering spectre haunting many Compton natives, he detailed a specific situation that thrust Kendrick into a one-on-one conversation with the reaper: “That trauma is so deep and so thick to this day. It’s never-ending, you know? Yeah. Cause there was always something happening. It was just, ‘How close are you to that individual that it happened to?'”

He continues, speaking on their close friend Chad Keaton, who in 2013 lost his life to gun violence while Kendrick Lamar was touring the country and cementing his superstar status. “Chad was a really hard one for Kendrick. It was really hard for him because Chad was younger than us. The little bro. And we talked to him…we were supposed to go see him, and we didn’t even get to see him, but we talked to him on FaceTime. I remember. I’ll never forget it. He FaceTimed me .. And we were on the bus talking to him, and we were telling him, ‘Bro, we’re about to come back and see you. We’re going to try to cut this run short and get back to you,’ and we didn’t make it back to see him before he passed.”

Jason Keaton, older brother of Chad, was sentenced to serve a term in prison as Kendrick Lamar began his ascent in the soundsphere. He asked Kendrick to promise him one thing before making it big: just look out for his lil bro.

Dave expressed how these events impacted both he…

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