As a cofounder of Gang Starr, Cary ‘Big Shug‘ Guy was born in Boston, Massachusetts, spending his formative years in the Murdapan [see: Mattapan] section of the city. Shug, along with his younger brother, DJ Suave D, and the late Guru initially formed the collective while attending Morehouse College.

An extended member of the Gang Starr Foundation, Big Shug would later go on to appear on Hard to Earn [“F.A.L.A.”], Moment of Truth [“The Militia”] and The Ownerz [“Capture (Militia Pt. 3)”], as well as the first three volumes in the Jazzmatazz series, before finally dropping his debut solo body of work, Who’s Hard?, in 2005.

First things first, last year (August 11th to be exact) marked the 50th Anniversary of Hip Hop — What exactly does that mean to and for you?

Well, the first thing for me is, I’ve been rapping from since the inception. You know, I’ve been rhyming that long. So therefore, to me it just means that something would continue to grow and that’s a great thing for me, man, and I’m glad to be a part of it because I’ll rap for the rest of my life and that’s how I see it.

To quote the late, great The Notorious B.I.G., “You never thought that Hip Hop would take it this far!” — Was this something that you ever could’ve imagined?

One thing about Hip Hop I always thought that it could get big. A lot of others didn’t believe in it like that, but I always did. So it’s great to see, you know, Hip Hop in commercials, on the radio more. And, even in Super Bowl Halftime shows. It’s so much more that has been accomplished when people thought it was a fad. When I started out (with) Guru people thought it was just a fledging thing, and me and him were a little bit too old for that, you know, this is what we would hear back then. So, I’m not surprised at how far it has gone, because I always believed in it.

What are some of your fondest, most stand-out moments / memories during your lengthy tenure in this thing called Hip Hop?

One of the fondest memories for me was, you know, just performing at the Montreux Jazz Festival. That was so great. Big crowds and people coming from all over the world. Watching us perform, Jazzmatazz, that was great. Also, when “The Milita” came out, it kinda hit. When I would come out on stage and do my verse, people would go crazy, and in all the stadiums and such and all (over) the world. It was so great, man, for me. And, the fact of being together with the fellas, Premier and Guru, and just touring the world. It was just great times, and it will always be remembered that way.

That said, what are your future and / or goals throughout the remainder of 2024 and beyond?

2024 you know, man, with life anything is possible. So what I’ll be doing is releasing a new album, I believe my 8th, titled Undefeated featuring DJ Premier. So all beats by DJ Premier. Some of the essence things with us, you know, the sound, and also, you know, some history and the making with vocals and different things that we talk about and discuss on there. Also, you know I’ll be continuing to release some more soul songs in that styling. And, you know, work on the movie of Gangstarr. So there are so many things left. But first and foremost, I got to have life, and as long as I have life I would do these things. So the first thing to come is my album Undefeated featuring DJ Priemer. And, a few others on there. Featuring my son Trumanye, Termanology, Singapore Kane, and such. And, some more movies; I’m glad to be in some more movies here, too.

Switching gears here, what exactly do you want people to get from your music?

When you hear my music, I want you to be satisfied, I want you to enjoy it. You know, it aint about all this…dig into real too much, it’s music, man. It’s the theme of life, so I want people to enjoy my music. Those that are fans to do so and those that are new, just to enjoy the music. Whether its Hip Hop joints, whether it’s me singing joints, whatever, you know, that’s what you get out of it. You’ll get some message, too, you know, you’re going learn a few things, gonna feel some passion, too, so there is a lot to come out in that regard. But at the end of the day, it’s music, man, and I want you to be able to vibe to that.

If you could collaborate with any one artist, living or dead, who would it be and why?

I used to rock with Biggie and 2pac, being that I was cool with them. Shoot, even Luther Vandross, I could rock smooth with him. You know what I mean, there’s so many I would rock with. Even today, probably like Lil’ Mo, D’Angelo, there’s a few, you know what I’m saying. There’s an endless amount of people.

If you could play any venue in the world, which one would you choose and why?

I actually like the House of Blues because of its intimacy, and it’s big but not to big. It’s always been like a good crowd at the House of Blues, so I would like to rock the House of Blues. But, there are so many more other places, too, like TD Garden, you know, Tweeter [now Xfinity] Center so I would you know. Any place and I would rock a lot of places. A lot, a lot of them and there’s not many more and I’ve done all that.

On a more serious note, are you happy with the current state of Hip Hop?

I think Hip Hop is always what it is. It’s gonna evolve. The current state is good because you have so many different choices and so many different styles of Hip Hop. I mean, rap. I think it’s in a good place because it’s always evolving and growing. So, I’m good with it. You know, as long as I keep doing my thing and everybody has their contributions and keep moving then so be it. There’s no time to be judgmental, man, just keep rocking.

What do you feel has and will continue to be the key to your longevity?

The voice; if you have the voice, and you continue to be creative and even you are not creative, but if you just still have the voice and that desire. People are gonna listen to your music for forever. So Longevity is just as long as I have life, I have opportunity. And, if I have the voice then I can continue to create this music and bring the music to the masses and the people. So Life is number one…so as long as I can live I will keep doing music and that’s the bottom line.

Do you have any other outside / additional (future) aspirations, maybe even completely away from entertainment?

I had a lot of years as a coach, maybe about 20. With my sons and different kids and different places. So, I coached for a long time. Now you know I do acting alongside with. So that’s what you can look for. And completely away from entertainment. Maybe I just want to be taking trips, you know. Maybe just take trips and see the world and things like that on the level of relaxation like, you know, instead of just performing.

What’s an average day like for you?

An average day for me is a hustle, man. One to the two, I have to basically makes the dots connect. So whether it’s the situation of earning money, musically or what have you, I’m always hustling. I get rest, I’m creating music, doing my hustle and just keep it movin’, man. Always trying to elevate to the next level. Always trying to put myself in that financial gain and trying to get in that position. So, you know, an average day for me, is I wake up, thank God, get myself together, prepare myself for the hustle. Learn, earn and grow, and be creative. I listen to a lot of sport shows, sometimes I just have it quiet in my vehicle, and I’m just coming up with some music and lyrics. That’s a daily thing, every single day, and make something good. The family eats. And, we keep it moving.

Please discuss how you interact with and respond to fans…

I always love the fans. I do features for fans, of course for pay. Every time we do a show, I walk through the crowd, always have in my 30 years or so. Just to show people, man, that you are with them. You know, man, I move through the crowd, take pictures. Sell merchandise. I’ve always been a part of the fan, and I appreciate them. Thousands listen to my music every month, so I’ve always interacted with the fans on a high level. I respect that.

What is your favorite part about this line of work? Your least favorite? And, why?

When you can rock and do shows. Covid kinda slowed things up, but you had to be in survival mode then. But, if you can rock and do shows, that’s my best part. And I like making the music, too. Those are great parts for me. The worst part is sometimes people don’t really support, or come to the venues like they used to, or want to, or say they would. For some, that’s pretty tough because you have a lot of part-time rappers who work and perform. Everybody ain’t a platinum artist. It’s not balanced in that way. So the worst part about it, is that I feel like that everyone should be able to make some kind of money. Everybody can’t because not everyone is as good as they think they are. But the fans will tell you that they are the consumers. But if more people could make money and have a career, that would be good…but then again, that might saturate it. So worst part about it, is people thinking that they are better than they are, not making money, and, you know, it is what it is.

What advice would you have for someone wanting to follow in your footsteps?

You must be diligent, you must believe in yourself because in this game of rapping, and music and entertainment, no one believes in you as much as you do. You know, you have to have that strength, that inner strength. Be patient. When it’s time to strike, you have to strike. It might not happen for all. But give it all you got. And if you feel like you have given it all you got, and it hasn’t happened, then you have to move on. But if it does, then continue to do your music, man. Continue to grow, make something that the people like, and that you like. Just keep it poppin’.

Looking ahead, say five or maybe even ten years from now, where do you see yourself?

Years from now, I see myself still making music. I see myself as an actor, doing some great role in a movie. Comical, probably more comical or something. I really see that. You know, I always say that with life all things are possible. So this probably will come to fruition. But, I see myself like that 5 to 10 years from now. Doing some great part in a movie. And, the Gang Starr movie will be out. You know, just trying to live and enjoy life.

Is there anything I left out or just plain forgot to mention?

We covered a lot of things. I want people to stay in tune. Big Shug ain’t going nowhere, music is invincible and forever, so I’m going to continue to make that. I have the podcast, the Danger Zone Podcast, with co-host Myster DL and Chef Tanya Nicole. I also have some other endeavors. Stay tuned for my son Trumanye, he has an EP out that’s called Yours Truly, and he will continue to make music as well.

Any “parting” words for our readers?

I just want to say to the people, “Keep on listenin’, I’ll keep on giving to it you. I love you all and stay tuned!”