We spoke to Ashley Mighty Bolton, founder of The Art of Dialogue YouTube Channel, about documenting the life and career of 2Pac and what it’s like archiving hip-hop history.
The Art of Dialogue has risen in popularity over lockdown thanks to its fearless approach to getting down to the truth. Chronicling the life of 2Pac, through interviews with the late rapper’s peers, enemies, and friends, the rising YouTube channel asks the kind of questions other interviewers seem to shy away from.
For example, openly gay Death Row singer Danny Boy was asked what it was like existing on a label where homophobia was rife; Lil Cease was quizzed on his best friend The Notorious B.I.G. phoning Nas to persuade him to jump on a song [“The Ugliest”] dissing 2Pac and whether this destroys the idea of the Ready To Die’ rapper being a peacemaker; and underrated singer Jewell was questioned on how being a woman might have stifled her progress under the alpha male tutorage of former boss Suge Knight. The result is a compelling interview format that consistently unearths new truths about rap’s golden era. (One explosive video went viral after Outlawz member Napoleon revealed Jada Pinkett-Smith used to beg 2Pac not to beat up Will Smith).
By speaking to people who were once hidden in the background — interviews also include former Death Row security lead Reggie Wright Jr, engineer Darryl Harper, producer Curtis “Kurt Kobane” Couthon, and Majesty, the brother of 2Pac associate’ Big Stretch — The Art of Dialogue tends to throw doubts on the official narrative, treating the days when Pac and Suge Knight burned rubber through the streets of LA with the gravitas of a historian dissecting the Fall of the Roman Empire. It’s no surprise the channel, at the time of publication, has over 229k subscribers.
“I’m trying to record 2Pac’s life from all angles,” says the creator and lead interviewer, 31-year-old Ashley Mighty Bolton. “I always make sure my interviews are about the person I am interviewing, and not just me. I see other platforms where the interviewer always talks over their guest and gives their opinion… I guess I felt like there was a hole in the market for someone to do it the opposite way.”
Bolton has no journalistic training. He started out blogging stories about film productions, including Straight Outta Compton, utilizing extras for exclusive information. But while looking into 2Pac history online, Bolton was hit with the nagging sense he could have asked better questions. Over time, he became obsessed with the art of interviewing; particularly, the challenge of finding fresh information about the contradictory mindset of 2Pac, an artist Bolton grew up studying after falling in love with his uncle’s All Eyez On Me cassette tape.
The Houston native — who grew up in a humble single parent household — has subsequently bootstrapped a successful hip-hop channel, paying for his own flights, camera equipment, hotels, and travel when conducting face-to-face video interviews. While he started out interviewing backing dancers and weed carriers, he’s now asking original questions to legends like Easy Mo Bee and Charli Baltimore, usually charming them with his relaxed manner.
“I’ve learned completely on the fly. It’s a long hustle [doing these interviews],” he said. “But it’s a good feeling building up your own thing and being self-sufficient. When people used to tell me I was recording history, I wouldn’t back myself, but I’m really starting to believe it now. I want people to watch my videos 30 or 40 years from now.”
Okayplayer spoke to Bolton about the Art of Dialogue’s success, the rise of rap interviewers who interrogate their guests with police-like tenacity, the immortal intrigue around Tupac Shakur, and why YouTuber interviewers are archiving hip-hop history
I guess some YouTube rap interview channels can come across like cocky FBI detectives trying to tempt out lurid details from their subject. When a rap interviewee makes a reference to violence, these channels continue to dig, sounding titillated by the prospect of generating viewing figures and teasing out incriminating information. I like that I never feel like that when I am watching The Art of Dialogue.
Ashley Mighty Bolton: A lot of these platforms are like an interrogation. I wouldn’t ever put somebody in the position for them to possibly get locked up. I wouldn’t ask them anything crazy or whatever, especially if I know they got a case going on. I guess I just try to keep it calm and keep it silent so my guest can be comfortable speaking. I am naturally very laid back and I think that translates to the person in front of the camera. I’m really trying to ask people the things everyone else is too scared to put to them. I recently did an interview with Lil Cease and even he was caught off guard with the stuff I was asking him because I guess he’s used to being asked the same two or three things about [The Notorious B.I.G.]. I am putting in hours and hours of research so I can ask Cease about the finer details of a song like “Long Kiss Goodnight” or why Biggie would release “Who Shot Ya?” when it could be misconstrued as a diss by 2Pac.
2Pac has been dead for over 25 years. Why in 2022 are millions of people still prepared to sit down and watch interviews with all of his aging affiliates?
The music he made was just timeless. 2Pac spoke in universal truths. Whether it was overcoming racism, women selling their bodies to survive, the strength of single mothers — these are all issues that are still going to be relevant 100 years from now. I guess people want to know about the mind that these songs came from.
It’s also about being creative and not just interviewing the same names, so you can provide a fresh perspective. People who are active in the industry are going to hold out on sharing information, but if you speak to an engineer from the 1990s, who is now retired, they’re going to be more honest, you know?
From interviewing so many people close to Death Row Records and 2Pac, what are some of the biggest things you’ve learned? It sounds like that place was a hotbed for toxic masculinity, right?
It was a whole lotta bullying and masculinity going on. You’ve got all these young folks, you know, that have got millions in cash, yet they are still acting up. It’s like: why were you still doing this? Suge Knight had $200 million dollars to his name, and I guess he didn’t know how to handle it.
When it comes to 2Pac, some people told me it seemed like he was bi-polar, and I can’t argue with that. He could do something great and then suddenly spark violence; like, he was always close to violence. It’s just crazy to think that the biggest rapper in America could get murdered for punching a gang member. Imagine you woke up tomorrow and Drake died in a hail of bullets for punching a crip; shit would be mind-blowing and crazy, right? I think the real reason Pac was prepared to punch a crip [Orland Anderson] in Vegas was out of loyalty to Suge Knight. He was loyal to a fault when it came to his friends… that’s always the impression I got.
As a lifelong 2Pac fan, was it weird interviewing Keefe D [the uncle of Orlando Anderson, the commonly accepted triggerman behind Tupac’s murder]?
Yeah it was very weird doing an interview with Keefe D, because you really don’t know what to expect. You gotta understand, man: I had to go to Las Vegas to do that interview, so I had to go to his territory and do an interview. I’ve never even been to Vegas before and I didn’t know what he’d be like. It was definitely awkward, but I can’t lie, bro: the dude is entertaining as hell! He’s low-key a bit of a comedian. I guess you’ve got to always appreciate the other person’s perspective and stay balanced, no matter where your passion lies. Keefe’s cousin Orlando was kicked to the ground by 2Pac and Suge; that’s the ultimate disrespect and violation. Sadly, there was always going to be consequences.
Where do you see yourself in the future? Is there anyone else on your interview hit-list?
I just spoke to Sharitha Knight, who is Suge’s ex-wife. I am trying to speak to everyone connected to the story. My dream interviews would be Jada Pinkett-Smith, Kidada Jones, Keisha Morris (2Pac’s ex-wife), Suge Knight, and probably Snoop Dogg. I just want to take it to the next level, and I am going to be doing more stuff about Biggie too, which will be similar to my interviews with Charli Baltimore. Eventually, I’d love to make documentaries.
I just want to ask those real questions, man. I’m not holding back or trying to make people in the industry have an easy ride. I am asking the tough questions because I really couldn’t care about any of that industry bullshit. I guess more and more people are realizing what I am doing on YouTube is about archiving history and doing journalism. Tupac and Biggie were Kings, and it’s important we get their stories from all angles. I think it’s also important that people who look like me, and come from where I come from, are the ones getting the opportunities to tell this history.
Thomas Hobbs is a freelance culture and music journalist from the UK. His work has appeared in the Guardian, VICE, Financial Times, Dazed, Pitchfork, New Statesman, Little White Lies, The i and Time Out. You can find him on Twitter: @thobbsjourno