A History of Oprah Winfrey’s Hot-and-Cold Relationship With Hip-Hop

In 1995, Oprah called on some of the biggest stars on television to give her audience members and viewers relationship advice. One of the participants was Queen Latifah, a hip-hop legend who was starring on the hit sitcom Living Single at the time. It was one of the first times that a rapper was invited onto the show.

In 1999, Will Smith appeared on The Oprah Winfrey Show for the first time. The rapper-turned-actor made the occasion a memorable one by walking Oprah through a step-by-step lesson of how to do the famous dance from the "Men in Black" music video. Getting the studio audience in on the fun, Will Smith and Oprah created one of the most lasting memories of a rapper gracing her stage.

Following the multi-platinum success of The College Dropout and the release of his heavily anticipated sophomore album, Late Registration, Kanye West was invited to appear on The Oprah Winfrey Show. The two Chicago icons had a lighthearted conversation about everything from their previous encounters to his meteoric success.

During an appearance on The Oprah Winfrey Show alongside cast members of the 2005 film Crash, Ludacris was criticized for using language derogatory to women in his music, resulting in the rapper feeling that he was being treated unfairly and his words were taken out of context.

In addition to claims that Winfrey initially didn't invite him to appear on the show, Luda also shared Oprah's reasoning for her reluctance to invite rappers on her show.

“After the taping, she pulled me into a room and we had a five-minute conversation,” Luda said. “What I got was that by having rappers on her show, she feels like she is empowering in them. It was like being at someone’s house who doesn’t really want you there.”

Luckily, according to Ludacris, the two have since made peace, ending one of Winfrey's most high-profile feuds with a rap artist.

After being lambasted by rappers like Ludacris and 50 Cent over here perceived slights and lack of respect towards hip-hop artists, Oprah attempted to set the record straight during a visit to New York radio station Power 105.1 in May 2006.

"I listen to some hip-hop," Oprah told DJ Ed Lover. "You know, I've been accused of not liking hip-hop and that's just not true. I got a little 50 [Cent] on my iPod. I really do. Love 'In Da Club.' ... Love that, and you know, love Jay-Z, love Kanye [West], love Mary J. [Blige]."

Winfrey's interview with Ed Lover was among her first public attempts to show her own love of rap music and would begin to change the tide in how artists and fans viewed the talk-show host-turned-mogul.

In spite of her sometimes rocky relationship with the hip-hop community, one rap artist that Oprah has grown particularly fond of over the years is Jay-Z. In 2009, Hov sat down with Oprah for an exclusive interview for the October 2009 issue of O Magazine, which took place in the rapper's stomping grounds, the notorious Marcy Housing Projects. Jay later referenced the moment on his song "On to the Next," stamping Oprah as good in the hood.

In light of the catastrophic earthquake that ravaged Haiti in January 2010, The Oprah Winfrey Show dedicated a live one-hour show to touching on the tragic realities of its impact with some of the biggest stars in music, including former Fugees member Wyclef Jean.

Wyclef, who traveled to Haiti himself to witness the impact of the earthquake and contribute to relief efforts, shared his experience in what was a tearful interaction between the rapper and Oprah.

In 2006, 50 Cent joined a growing list of rappers voicing their disdain for Oprah's perceived lack of respect for rap artists. "I think she caters to older white women," he said then, adding "Oprah's audience is my audience's parents."

The G-Unit general continued his assault on Oprah over the years, even naming his dog after Winfrey in a show of disrespect. However, the two eventually sat down to make amends in 2012.

During an appearance on OWN's Oprah's Next Chapter, the two moguls hashed out their differences on camera for the world to see. Although they agreed to disagree on some topics, they ultimately decided to bury the hatchet and move forward on an amicable note.

"This is a huge milestone for me—just being in your presence and on the show," 50 said. "That's a huge accomplishment."

In 2013, Oprah sat down with rap legend LL Cool J as part of her Oprah's Next Chapter series and discussed his career, marriage, abusive childhood and the importance of family.

LL was joined by his wife and their four children at one point during the candid and heartfelt conversation. Four years later, the two reunited when LL Cool J appeared on Oprah's Master Class.

In February 2008, Snoop Dogg voiced his displeasure with his music being referenced during an episode on misogyny in hip-hop without being invited on the show to defend himself.

“I really was offended, because I kind of like her,” the West Coast legend said. “Liked her. I’m very articulate, very intellectual. She didn’t even get a chance to even know me.”

While Oprah never reached out to Snoop to appear on the show, the two seemed to have squashed any ill feelings when they appeared in a photo together alongside Oprah's BFF Gayle King at an Oscars party in 2014.

Ice Cube was one of Oprah's earliest hip-hop detractors—he expressed his views on Winfrey during a 2006 interview.

"I've been involved in three projects pitched to her but I've never been asked to participate," the rapper shared, referencing to his movie Barbershop. While Oprah didn't directly respond to the critique, the mogul praised Cube and F. Gary Gray's 2015 N.W.A. biopic Straight Outta Compton, deeming it “powerful” and “eye-opening rap education," in a series of tweets after watching the movie.

While Oprah and Kanye's first meeting was lighthearted in nature, the two Chicagoans haven't always seen eye-to-eye. Winfrey took umbrage with Kanye's 2016 single "All Day," warn Paul McCartney not to appear on the song, which the Beatle revealed during a 2016 interview.

"People like Oprah—who's a little conservative about that stuff—said, ‘You shouldn't do it, even Black people shouldn't use that word,'" McCartney said, alluding to the n-word. "I said, 'Yeah, but it's Kanye!' And he's talking about an urban generation that uses that word in a completely different way. It's the context. So I was actually pleased with it."

Winfrey also shot down talk of a potential Kanye presidency when asked about the rapper's political aspirations: "Don't even imagine it."

In February 2018, it was announced that Russell Simmons' passages from Oprah Winfrey's spiritual self-help book The Wisdom of Sundays would be removed from all future printings amid allegations of sexual misconduct and abuse.

Oprah, who previously hosted Simmons on her show Super Soul Sunday in 2014 to promote his own book, Success Through Stillness: The Simplest Path To Meditation, had struck up a friendship with the rap pioneer over the years, but in light of the accusations levied against him, that relationship appears to have run its course.

Having softened on her stance and views on rap music over the years, Oprah showed just how in-tune she is with the times in April 2018, when she revealed to the world that she too was swept up in Cardi B mania.

On the day that Cardi B's debut album Invasion of Privacy was released, Oprah Magazine's Instagram account posted a photo of Oprah sitting with her eyes closed. The caption read,  "Listening to that new Cardi B album." Cardi reacted exactly as you'd expect, reposting the image with an all-caps exclamation.

Oprah's growing love for rap music reared its head again during a photo shoot for the September issue of O Magazine, as the billionaire mogul got her groove on to Young Thug while posing for the camera.

In a video posted on the magazine's Instagram page, Oprah can be seen dancing as Young Thug's verse on Camila Cabello's "Havana" plays in the background, a moment that quickly went viral and stands as the latest show of her embrace of hip-hop music and culture.