By Megan Fitzgerald

If you missed Sheena Easton’s “Morning Train” in the 80s, she’s headed full steam ahead to The Studio at Mizner Park on Saturday, May 3, 2025.  The two-time Grammy winner’s iconic career has spanned decades,  including collaborations with music legends like Prince, as well as successful stints on Broadway, television and film. Ahead of her upcoming performance in Boca Raton,  OutClique Magazine caught up with Sheena to talk about her early career, her current approach to performing, and what fans can expect from the show.

You rose to fame internationally in the early 1980s. When you look back at that whirlwind, what stands out to you most about those early days?
“Oh, it was a blur. My life was just a nonstop moving experience where I was literally working and traveling constantly, and I never felt like I was at home. Even though it was the most commercially successful time in my life, I couldn’t say it was the happiest—and it’s certainly not something I want to repeat. I like my life now because it has balance. I have a family, and I work when I feel like working. I work because I enjoy it, but when I want to take time off, I just take time off. I never allowed myself to even think that way in the ’80s. I felt like this wonderful thing had landed in my lap—all these opportunities—and I was raised with a strong work ethic. The belief was, if work comes up, you just do it. But now that I’m older, I feel like I paid my dues. I did all of that. I can kick back a little bit now.”

Has performing changed for you at all, or do you still feel the same way when you get on the stage?
“Oh, it’s changed drastically. I didn’t love it at the start. It’s hard to explain—I went to drama school, and that was my dream, to be a performer—but when you step on stage in front of a large crowd at a young age, and you’ve got all this pressure, things to prove, and record companies expecting you to promote the album, there’s a lot on your shoulders. It’s hard to just let loose and enjoy it. You’re really conscious of the pressure and what’s expected. When I look at young artists today, I imagine it’s the same for them. It took a long time before I could relax and just say, ‘I’m going to have fun, just going to have a blast up here.’ Now, it’s something I look forward to. I don’t feel that kind of pressure anymore, so I can just have fun with the fans and enjoy the music and the band.”

For your upcoming show in Boca, how do you go about choosing your set list? Do you perform your originals as recorded, or do you reinvent them?
“I’ve found from experience that when fans come to a show, they’re coming to hear the songs they love. They’re coming to hear the hits because they have memories associated with them. We all do that—put on an old favorite album, and it takes us back in time. Sometimes to a broken heart, sometimes to a great or sad time in your life. So I really think that for the major hits, they want to hear them the way they remember them. I don’t mess with those too much. I like to give them what they’re expecting. Then I throw in some curveballs—I do some covers and other songs that maybe they’re not expecting, but they mean something to me. I connect the dots with those, and I can see their faces light up like, ‘Oh, I remember this!’ So yeah, I mix it up a little, but I don’t mess too much with the hits. I let them have their hits.”

You’ve collaborated with icons like Prince. What did those experiences teach you about your own artistry?
“They taught me to be less afraid of making mistakes, to just go for it, and to be myself no matter what people might think. Not everyone’s going to be a huge fan of every collaboration an artist does. You have to just say, ‘I’m doing this for me.’ If it’s a success, great. If it isn’t, I’m still doing it for me—because it’s fun. Working with Prince especially taught me a lot. He truly was someone who would go into the studio—and I’m not saying he would wing it—but a lot of producers and writers have a game plan and they stick to it, like a roadmap. But Prince, if something happened accidentally—if I was singing and hit a wrong note or went off on a tangent—he’d be like, ‘Oh, that’s interesting. I like that. Let’s go with that.’ He’d do the same with music. He’d play me the structure, then change his mind and arrange it differently. Watching him work on our material and his own, I saw how free he was. That was a wonderful experience. It wasn’t that common back then. Maybe more now—but not so much then.”

If you had to describe your live performance in just three words, what would they be?
“A total blast. I have so much fun up on stage. One of the things I enjoy most is talent—I love musicians, I love other artists—and my guys are such talented players. It never gets old for me, hearing them and watching them work. I love connecting with the audience. I love seeing the look on people’s faces when you start the intro to their song—they’re waiting for that one, and they’re like, ‘Yes!’ It’s a lot of fun.  I hope they walk away feeling—this sounds cliché—but that we shared the experience together. That they’re not getting performed at. It’s not something that’s just thrown at them. I hope they see that I’m experiencing the fun with them, loving being in that moment. I hope they come away knowing we all had a great time, and that the songs brought back memories and helped them reexperience special times in their lives.”