Nancy Grace found herself in the hotseat two nights ago when 2 Chainz (or Tauheed Epps for the uninitiated) turned the tables on her when they (for some God-awful reason) decided to debate marijuana legalization. Despite her ridiculous attempts at initiating a modern reefer madness, Chainz stood taut, and taught the oft-ridiculed shock jock a thing or two — when he could get a word in.

It was pretty glorious to watch. The rapper isn’t necessarily known for his lyrical prowess, but add a sweater and some designer frames and that man cooked up a modern debate masterpiece. But it isn’t the first time Hip Hop and the talk show circuit has joined hands. Nope. And whenever they have the results have often been hilarious looks at how the wider world views Hip Hop standing in stark contrast to how Hip Hop views itself.

Here, we took a trip down memory lane in order to unearth seven other times when Hip Hop and mouthpieces for the wider culture at large went head-to-head.

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2 Chainz On Nancy Grace

Although Nancy Grace uttering the words “Smokin’ California weed with California hoes, truuu” already makes this debate classic, it was the logical words of 2 Chainz that had Hip Hop and marijuana fans alike nodding their heads in agreement. The debate was sparked (no pun intended) by recent footage of parents making their toddlers smoke on that loud. The HLN host attempted to use these videos to defend anti-legalization, but 2 Chainz beat that argument up like Rampage, stating “you can’t use these particular stories to define everybody that has recreational use.” This pretty much shut down Grace’s entire argument, but it didn’t stop her from repeatedly trying to bring the focus back to the footage. The conversation culminates with 2 Chainz illustrating how taxpayer money was wasted during an incident that involved marijuana residue being found on his tour bus. The stunned silence from Ms. Grace that followed? Priceless.

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Dame Dash & Cam’ron On Bill O’Reilly

It’s no secret that Bill O’ Reilly and Hip Hop have the same relationship as 2 Chainz and broke individuals. So in an attempt to portray the negative effects Hip Hop has on children, Bill claimed he would simply serve as moderator for a debate featuring an inner city high school principal versus Harlem’s own Cam’ron and Dame Dash. Expectedly, O’Reilly quickly abandoned his moderator role and also joined the debate. Unexpectedly, Cam and Dame made him look like a substitute teacher that was just too old and too slow to keep up. In some of the most entertaining television Fox News has ever produced, the hustlers from Harlem looked like Kobe & Shaq, verbally hitting O’Reilly from all angles and constantly keeping him on back pedal. In doing so, they were able to successfully describe the positives their music and actions have on children, including this gem from Dame “If an eleven-year-old were to imitate Cam’, what they would be doing is becoming a CEO of their own company.” But although they both dropped plenty of knowledge, it was Killa that provided the quotables that still got us crackin’ up. Whether it was telling the principal “tuck it in you done for the night, you got class tomorrow” or the infamous “you mad?” To a visibly frustrated O’Reilly, this clip just adds fuel to one of Hip Hop’s eternal burning questions: why the hell doesn’t Cam have a show yet?

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Cam’ron On 60 Minutes

It’s one of the most polarizing interviews in Hip Hop history, and one that shined a very bright light on the mindset of millions of individuals that were raised in the streets. During the 60 Minutes interview, when asked if he would inform police if there was a serial killer living next to him, Cam’ron calmly responded, “If I knew the serial killer was living next door to me? No I wouldn’t call anybody on him, but I’d probably move. But I’m not going to call and be like, the serial killer’s in 4E.” As one could imagine, this didn’t go over too well with 60 Minutes viewers. In the Hip Hop world however, it seemed like reactions were split between two camps: the “those comments were ignorant and an embarassment to Hip Hop” camp, and the “he’s just speaking the truth, snitching is not an option” camp. Although he stayed firm on his stance, Cam did understand the severity of what he said and issued an apology, “Looking back now, I can see how those comments could be viewed as offensive, especially to those who have suffered their own personal tragedies or to those who put their lives on the line to protect our citizens from crime.”

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Wu-Tang Clan On The Daily Show

After a year filled with inner turmoil for the Wu-Tang Clan, it was definitely a sight to see when all nine living members appeared on The Daily Showlast year to promote their latest projectA Better Tomorrow. It was a special moment, seeing that just months prior differences between RZA and Raekwon had Bobby Digital saying things like “If we don’t come to terms within the next 30 days, then this will either be an album without Raekwon or an album that never sees the light of day.” Fast forward to August 2014 however, the entire Wu is present and even able to joke about the riff within the crew with Jon Stewart. RZA provided another quote, except this time speaking about a positive future for the clan “Wu-Tang, we have something in common with each other – a brotherhood, a respect. And when we said a better tomorrow, we’re starting to make a better tomorrow for ourselves, but also to inspire a better tomorrow for the world.” Now although the album didn’t exactly live up to the hype, their appearance on The Daily Show was the first time in a long time we all saw solidarity with the brothers from the slums of Shaolin.

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Slim Thug On The Daily Show

In a culture that’s sometimes a bit too focused on staying hard and “keeping it real,” it’s always refreshing when a Hip Hop artist is able to chill out a bit and laugh at themselves. Slim Thug did exactly that on The Daily Show: With Jon Stewart back in 2009. In a hilarious mock interview with Daily Show correspondent Wyatt Cenac, Slim Thugga depicts how the recession has hit one group in the country especially hard: rappers. He goes on to talk about the trials and tribulations of downsizing his tour bus to a van, eating at stripclubs instead of making it rain, and the crisis involving the smaller number of video hos available at shoots. The Boss Hogg Outlaw followed up that appearance the next day by premiering his parody video for “Still A Boss.” The track also comically highlighted rappers in a recession, with Slim spitting “I don’t pop bottles at the club, it costs too much / Better take some shots of Patron and shut the hell up / Plus up at Costco, it’s half the cash / I buy a bottle for what you’re spending on one glass.”

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50 Cent On Oprah

Jay and Beyonce might have had $1 Billion going down an elevator, but when Oprah interviewed 50 Cent on Oprah’s Next Chapter in 2012, over $3 billion was relaxing in 50’s grandparents’ house that day. It was an interview many thought would never happen as a result of their very public feud. Fif’ had felt Oprah was constantly attacking Hip Hop, more specifically his style of rap, ultimately accusing her of losing touch of her roots, “started out with black women’s views but has been catering to middle-aged women, white American women, for so long that she’s become one herself.” Yup, pretty easy to see why people thought this interview was never going to happen. But it did, and it featured a very honest 50, who discussed the beef was simply “strategy,” and saying, “I had to create reasoning. If I can’t be your friend, at least let me be your enemy so I could coexist.” They’ve done a good job of coexisting since then, and have definitely come a long way from 50 naming his dog Oprah. Ouch.

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Jay Z On Oprah

There’s only a few people in the entertainment industry that can make Jay Z money look like peanuts, and Oprah Winfrey is one of those people. When Hov’ sat down for an interview with the multi-billionaire back in 2009, it was dope to see two of the most successful and influential figures in the African-American community chop it up about life and their careers. When discussing their success, Oprah pointed out their similarities, starting with their humble beginnings, “Neither of us had a vision or a plan for all of this… so what do you think made all of this happen?” Of course, Jay was as cool as the other side of the pillow (shotout to Stuart Scott), responding with, “I think it’s the passion for what you do… and finding something that you can be true to… something that’s really close to who you are as a person.” The interview covers plenty of other avenues as well, from a day in the life montage following Jay through his offices, all the way to him teaching Oprah how to spit a few bars. Hova and Oprah, excellence and success at its finest.

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Killer Mike On CNN

When it came to Hip Hop’s voice regarding social issues in this country, nobody had a louder mic than Killer Mike in 2014. His conversation with Brooke Baldwin on CNN came just a day after Mike penned a powerful op-ed piece for Billboard, which featured this chilling statement regarding the death of Mike Brown, “I found no new words. I have no hope-filled insight to deliver. I only have this warning to all Americans: Whatever this country is willing to do to the least of us, it will one day do to us all.” During his CNN stop (which was shortly followed by one at FOX News), he discussed a dangerous evolution with police officers and how their heading in the wrong direction, “We have essentially gone from being communities that were policed by people from the communities to being communities that are policed by strangers, and that’s no longer a community, that’s an area under seige.” He might of had a career year musically, but Killer Mike becoming the voice of Hip Hop was his greatest accomplishment in 2014.

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