While Larry King admitted on several occasions that he “didn’t appreciate Hip-Hop,” the legendary interviewer opened up his show to a plethora of rap stars beginning in 2014.

His lack of appreciation wasn’t malicious in the slightest. Raised on the sounds of Frank Sinatra and jazz, Larry King merely didn’t understand the genre. But with each interview he strove to educate not only the public about Hip-Hop’s cultural power, but himself. He often was hyper-focused on the lack of gay rappers within the industry, as well as the genre’s use of the N-word, and asked about it unflinchingly.


In turn, Larry’s signature open-ended questioning made for some truly illuminating moments, where some of today’s biggest rappers were given the space needed to speak on their craft authentically. Here are some of Larry King’s best rap interviews that show he was truly a master of getting artists to open up.

Pusha T

The future president of G.O.O.D. Music spoke authentically about the business of Hip-Hop in his interview with Larry King back in 2014. When King asks him where he sees Hip-Hop going, Pusha candidly speaks on how corporate America has undoubtedly taken part in capitalizing on Black culture. “The corporations, the people that are successful, are the ones that hired that guy to put their finger on the pulse of urban culture.”

Larry King, who over the years was very open about his inability to digest rap, asked soft and fairly open-ended questions about the genre as a whole, in response to which Pusha T was able to flex his genuine knowledge and respect for the genre. He breaks down why he thinks the N-word should be banned, where Hip-Hop came from, and why moving forward it will be the biggest thing on the planet, all while King listens and genuinely absorbs the new information.

Tyler, the Creator

A throughline in most of Larry King’s rap interviews is that he often asks his guest why there doesn’t seem to be any openly gay rappers. He asked Tyler, the Creator – who came out a few years later – the same question in 2014. “Do you think we’ll ever have a gay rap artist?” King asked. “Maybe one day, but like, why does that sh*t matter? Like if he wanna f**k dudes like why does that matter? Why do we care?”

T-Pain

Despite his legendary status in the culture, T-Pain has been disrespected more than a few times within the culture, and despite the solid quality of his recent albums, it just doesn’t seem like he’s been getting the love he rightfully deserves. In that respect, his candid interview on Larry King Live was surprisingly refreshing. King’s open-ended questions gave T-Pain space to truly illuminate us on his craft, and it allowed his brash authenticity to shine through. “People try to stay away from me,” he said. “I got a bad case of telling the truth.”

Common

The Common interview with Larry King is fantastic because of Barren Davis. The former NBA star asked more detailed questions that helped push Common to enlighten Larry and the viewers on the violence in Chicago. He broke down how the violence occurs and elaborated on the duty he felt to help his city and create an album for his city.

Snoop Dogg

Snoop and Larry have had some truly incredible moments over the years. The two had such a magnetic connection during Snoop’s first appearance on Larry King Live that the duo maintained a close friendship. Snoop even taught Larry how to rap at one point. Watching their relationship grow was a hilarious and often heartwarming experience.

DJ Khaled

While DJ Khaled may be known as a vivacious meme-able motivator, his conversation with Larry King was surprisingly transparent and forthcoming. He talked about what it was like being a Palestinian, specifically in music, his bitterness about the Israeli-Palestinian conflict, and how it’s his duty to “promote peace.” “It means more people like to say let’s come together, let’s do some things. Let’s show people that we can come together.”


Wiz Khalifa

“Hip-Hop is new to me,” Larry King admitted to Wiz Khalifa. “How would you define it?” Wiz Khalifa seemed to really appreciate the question, and what followed was an educational moment for Larry as he learned how the culture was started by Black people and how it slowly became more and more inclusive over the years. “It’s a lifestyle, it’s a culture, and it’s for everybody now, you know what I mean?” While Wiz is often stoned and goofy for interviews, he was relaxed and serious when speaking with Larry.

Mac Miller

There was always something slightly intimidating about Larry King’s old school, no bullsh*t demeanor. His questions were always direct, and his responses to the answers are always candid and authentic. When the late Mac Miller sat down to speak with the legendary interviewer, his physical and social anxiety was palpable, and several nervous jokes he made went over Larry’s head or garnered no response.

Still, what resulted from these moments was one of King’s most earnest and relatable interviews. Mac’s timid behavior simply mirrored that of any mere mortal were they to be suddenly placed across from Larry King.

During one moment of awkward silence, Mac interjects that he can’t believe he’s being interviewed right now by Larry King. Larry makes sure to meet him halfway and plays along with his quirky banter for a few moments, at one point calling him “Felonious Alfonso,” a genius alias that Mac should have immediately trademarked.

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