Q: Did hip-hop changing ever make you feel disconnected from it?

Of course. I feel disconnected from it every day. No one cares about talent or message anymore. Now it’s a clout chase, so trying to fit into the modern-day form of the music is a no-go for me. I like the realness of back in the day.

Q: What’s something artists fake online that people don’t realize?

Followers! Fake followers! Of course, there are the rentals and all that, but that’s cool as long as you ain’t online claiming you own something you don’t.

Q: What’s harder now — making music or getting attention?

Definitely gaining attention. There are so many people who make music and are good at social media. I’m not great with social media, so I’ll be overlooked because I haven’t mastered self-promotion.

Q: You seem more focused on identity and branding now. Why?

I’m focused on that area because not only can you build a legacy that lives by itself and isn’t attached to your everyday situation, but it also allows you to put other people in position to grow along with you.

Q: What did performing again after 25 years feel like mentally?

Scary! Muthafuckers just staring at you like, “Who is this muthafucka?”

Q: What’s one thing younger artists misunderstand about longevity?

It’s hard to come by, and you need to keep your face card clean in these streets and in the industry. True longevity comes from how well you treat people — not just the people who can do something for you, but everybody.

Q: What kind of legacy are you actually trying to leave behind?

I want to leave behind proof that I created, built, helped, documented, and stayed myself through all of it. I don’t just want people to say I rapped. I want them to say I put ideas in motion and helped create space for other people too.

Q: Do you think artists become addicted to attention more than music?

Yeah. It’s like a drug. I think some of these artists never got any attention before they started doing music. Before I started rapping, I was a skateboarder. I competed and had sponsors, so I’m used to attention.

Q: Have you ever felt jealous watching less talented people succeed faster?

I wouldn’t say jealousy. I would say frustration that I didn’t get my chance, and that the people around me who were going to benefit from my success didn’t put in more work as well.

Q: What’s the difference between confidence and insecurity in rap culture?

I’m not really sure because I’m confident and insecure about a lot of things. I think it’s part of being human.

Q: Do you think your pride ever slowed your career down?

I wouldn’t say pride, but I’m very principled and I don’t back down when I believe in something. I don’t want a lot of money and still feel uncomfortable with my day-to-day dealings.

Q: How much of the music industry is built on illusion?

All of this shit. Next question!

Q: Have you ever looked successful while struggling financially?

Of course, but that’s because I just like to look fly and I have bad spending habits. Don’t blame me, blame Nike. Lol. I’m struggling right now. I got a lot of bills. I’m not sleeping on somebody else’s couch. I maintain my situation the best way I can, and I ain’t rich. In my opinion, if you have less than a million in the bank, you are struggling.

Q: Why do so many artists spend money trying to “look like they made it”?

Because the opposite is looking broke, and unless that’s what you’re going for, it’s common knowledge that the average fan is not going to take the words seriously of a person who doesn’t look like they got some motion.

Q: What’s the biggest financial mistake artists make chasing fame?

Spending money with all these playlist people and middlemen who promise to do something for your career. The majority of these hustles are scams.

Q: What’s something you still battle internally as an artist?

How much longer do I want to keep doing this? The only happy part is making the music. Everything else is fake people, fake friends, and a bunch of capping-ass people. This shit is horrible for your mental health.

Q: Do artists talk enough about fear?

No! They think every artist is supposed to be fearless when they are just human. I fear a lot of things, but I’m not trying to work through my fears. I’m just trying to be brave enough to face the fears.

Q: Have you ever questioned whether continuing music still made sense?

Yeah, but music is forever and so is a message, so making music will always make sense. Trying to put it out and promote it is another question altogether.

Q: What’s the hardest part about friendships in music culture?

Most of these muthafuckas are fake. It’s better to just lock in with your real people and keep your peace. One day they love you, then as soon as you look like competition, they will find a way to hate on you. And if you’re like me and don’t mind speaking your mind and acting on problems, then it’s better to keep associates and stop making friends with these niggas.

Q: Do success and attention change the way people treat you?

Yeah. When you are up, they shout you out, and when you are down, they won’t even pick up the phone. But you already know what time it is.

Q: Have you lost relationships because of pride, ambition, or ego?

I never lost a relationship I ever needed to keep.

Q: What does getting older in rap teach you about yourself?

That when you were younger, you didn’t know shit — because now that I’m older, I barely still know shit.

Q: What matters more to you now: being famous or being respected?

Respect goes a long way. I don’t need to be famous. Respect kept me moving this long, and when you really did some real shit in real life around real people, then you understand how much respect really counts.

Q: What scares artists more — failure or being forgotten?

Being forgotten.

Q: Do you think social media made artists more connected or more fake?

Definitely more fake. These dudes on something else, boy, I tell ya! Lol.

Q: What do you think people misunderstand about you the most?

That what you see is what you get, but you won’t really see what you’re getting if you don’t pay close attention. I’m layers of many things, not just a rapper. Rapping is probably midway on my list of talents, and it’s not even my biggest love in life.

Q: If music disappeared tomorrow, who would Bobby Wolf still be?

Let’s see: a comic book collector, toy collector, OG skateboarder, graphic designer, web designer, part-time off-the-stage comedian who still looks fly half the time with no effort. But to be frank, I would be me — and there is only one of one there. So yeah, that’s it.

Q: Any shout outs?

Nope