For nearly 30-years, Jamaican entertainer Sean Paul (née Sean Paul Francis Henriques) has been blessing our ears with some of the hottest dancehall tracks of all-time. With hits like “Baby Boy” ft. Beyoncé, “Gimme the Light”,”Give it Up For Me” ft. Keyshia Cole and so many more—there’s no denying that the Kingston-born artist has solidified his place as one of the genre’s greats.

Focusing more on singles during this stage of his career, versus albums, Henriques recently dropped tracks “Rebel Time” with Beres Hammond and “Nina Bonita” with Feid. But for him, life these days is all about spending time with wife Jodie Stewart and their two young children, both born when the singer was in his 40s.

Even with three decades of performing for fans and hitting global stages, Sean Paul is not letting up anytime soon. EBONY was in the building for one of his latest performances, where he headlined for Cayman Islands’ Out of This World Fest. The singer and rapper brought all the vibes for his set, making sure to give fans just the right amount of nostalgia.

We sat down with the legendary performer after his show to learn more about the keys to his career longevity, becoming a father later in life and his Father’s Day plans.

Sean Paul during his Out of this World Fest set. Image: DeAnna Taylor.

EBONY: You’ve been in this industry since 2004. What do you think have been the keys to your career longevity?

Sean Paul: Loving what you do is something that will keep you doing it. That is the key to being happy. You can measure success in many ways, but it’s not always about money. I want to encourage others that when you love what you love, make sure you’re doing it positively and that it doesn’t offend or hurt others. I always take that into consideration and I think people see that in me.

Talk to me about your Jamaican roots and why it’s important for you to share your culture with the world?

Jamaica is a small territory, but we’ve had a large impact on the world. From our food, language, and culture—I’m proud of that. I want to encourage other Jamaicans abroad to keep working hard, but don’t forget the culture.

When you’re on stage, you always make sure to dedicate a song to your children. What is fatherhood like at 50-years-old, and what are you most looking forward to for Father’s Day?

Let me tell you something. I literally just canceled a show that was supposed to take place on Father’s Day because I want to spend it with mi pickney (children in patois). Fatherhood is a new chapter of life for me, you know, I’m someone who did this late. But, they keep me feeling young, and remind me so much of myself. I think they are the best song I every wrote. It’s all still new for me, but it’s such a blessing.

You’re one of music’s collaboration kings. Can you pick a favorite collab of all-time?

I could never pick only one. Man, I’m just feeling blessed to still have my career and for those who heard me and said, “Man, this guy can spit,” and took a chance on me. There were times when I was the smaller artist. Even now, there are some younger artists who have way more streams than me, but they are still taking a chance. I just give thanks, because there’s nothing like just being able to truly do what you love.

What’s coming next for Sean Paul?

I just released a collab with Beres Hammond; he’s a legend in the music business and from Jamaica. The video drops next week. I’ve also been doing a lot of Latin work lately. Looking forward to putting out a few singles with some of the artists from my camp. So just look for me on your airwaves very soon!