Everett Osborne on 'Why Did I Get Married Again?,' Faith, and Entering the 'Power' Universe

Everett Osborne is a Los Angeles native whose path to acting was anything but traditional. A former professional basketball player who played overseas in Australia, Osborne discovered acting during the COVID-19 pandemic after studying psychology and appearing in several commercials.

He eventually found his calling in the craft, leading to his breakout performance as basketball pioneer Nat “Sweetwater” Clifton in Sweetwater. His growing résumé also includes appearances in Sistas and Chicago Fire, with his latest work taking him into Tyler Perry’s Why Did I Get Married Again? and the Power universe.

In Why Did I Get Married Again?, Osborne plays Wesley, a football player who is preparing to marry Jasmine (Armani Greer), the daughter of Angela (Tasha Smith) and Marcus (Michael Jai White). The wedding brings together the next generation of the franchise while reconnecting them with the characters audiences have known since the original films.

But for Wesley, the wedding is only part of the story. His relationship with his mother, Roselyn (Taraji P. Henson), is strained, and as secrets and complicated family dynamics begin to surface, Wesley is forced to navigate love, loyalty and the meaning of family.

For Osborne, the role came at an interesting time. He had been thinking about marriage and partnership in his own life when the opportunity to join the franchise arrived. That personal connection helped shape how he approached Wesley, not simply as a character in a comedy, but as a man committed to his relationship and willing to fight for the life he believes in.

“I think Wesley saw a greater vision of why they wanted to be married even if no one made sense of it,” Osborne tells The Quintessential Gentleman. “I think his need and love for Jasmine and how he views family, the relationships dynamic, I think he took that seriously, even through all the mistakes.”

With the film, Osborne joins a franchise built around conversations about love, marriage, family, and the complicated realities that exist behind relationships. In our interview, he talks about the headspace he was in while filming, working with the Why Did I Get Married OGs and entering into 50 Cents’ Power universe.

[Interview has been edited for length and clarity]

What was it like getting the call to be part of Why Did I Get Married Again?, especially knowing the franchise and what it has meant to Black audiences?

Everett Osborne: I was thinking about marriage during this time. I really wanted to—I was planning on. I was raised, once again, I come from a Southern household, so I was raised on love. My grandparents were married for 50-plus years, still together to this day. I was raised on partnership and wanting that. So the journey to get there ain’t easy. They don’t tell you that far. I did arrive there around this time last year. I was thinking about it. And to be honest, what really happened was my best friend got married in Cabo. I was one of his groomsmen. And it just inspired me to see young Black love. And to see how we were all happy. How we came together for something special, it inspired that in me.

So when this audition came, I was like, “Man, how ironic is this? This is something I’ve been thinking about, dealing with, and just wondering and praying about.” So when it came to me, I was honored. It was fun. I took it on as a warrior. I didn’t take it on as a comedy. I looked at the story first. The story was so special to me and close to home. Then knowing it was TP (Tyler Perry), knowing it was a Why Did I Get Married? franchise, it was an honor.

Did doing this movie give you the itch for marriage?

Everett Osborne: It wasn’t really an itch. It was out of pure alignment. It was just like where I was called to during that time. It wasn’t like baby fever. It just has to be the right time. So I’m not seeking that at all. I’m not running from it either, but I’m not seeking that. I find more value in friendships right now, or just honest connection with people, and taking my time and focusing on my work and my family.

What do you think is one of the challenges people currently have when they’re trying to navigate relationships and seek marriage?

Everett Osborne: Hey, listen. I’m not the relationship guru. This is my first time doing life just like everybody else, so I definitely don’t have the answers. But from what I’ve seen, I don’t think you can have love without God, man. I think love is supernatural. I think you do need to tap into some source beyond yourself to show up for somebody when you don’t feel like it. I think you need to be able to find a way to have empathy and forgive. Something I’ve been working on this whole last year when I’ve been in New York working. I’ve just been focusing on having a pure heart. What does that look like? No matter how much love you lost, no matter how much someone disrespects you, no matter what you go through in life – personal relationships, career – can you still show up to whatever you call to with an open heart as if you never lost? Can you still climb? Can you still go to the next level, meet the next person, the next woman, the next man with an open heart, with a pure heart, as if you wasn’t just cheated on, as if you wasn’t just lied to? So I think you can’t do that without God for me. I think that’s something that’s special: maintaining a pure heart, open heart, and providing space for people to grow, people change, people evolve.

Let’s talk about Wesley. How do you see him?

Everett Osborne: Wesley is just a warrior for love. I think Wesley is a soldier for love. And sometimes things aren’t perfect. Sometimes things aren’t perfect. Things aren’t white picket fence. You gotta push through. I think Wesley saw a greater vision of why they wanted to be married even if no one made sense of it. I think his need and love for Jasmine and how he views family, the relationships dynamic, I think he took that seriously, even through all the mistakes.

A lot of people felt Wesley went too hard on his mother. What do you think?

Everett Osborne: There’s no greater relationship on this earth I got outside of my mom that God gifted me with. I love my mama to death. So I think Wesley loves his mom too, but the difference between me and him is the management of emotions and how to handle what you feel and process what you feel in real time, and then words, thoughts, feelings, and stay respectful. So I think Wesley was disrespectful to his mom. I think there’s certain conversations they could have had. There’s so many different dynamics going on where I think Wesley was just broken. There’s so many ways of just disrespect that he felt. You know, when people feel disrespected, they sometimes replicate what they feel from other people.

What was it like being on set with Tyler Perry, Taraji P. Henson and the rest of the cast?

Everett Osborne: The truth is, we got a group chat right now, especially the young generation. We are like, I was gonna say best friends, but we really family. When I got there, man, I just locked my head in to the hotel. I didn’t leave. I didn’t talk to nobody. I had to do my work to prepare because I know how fast Tyler Perry shoots. We did this in four days. So I wanted to prepare. But once I got out them walls, I saw the city. I saw Taraji, I saw Tasha, I saw Tyler Perry, I saw my castmates, Michael Jai White, Rich. I mean, these guys are legends. Lamont, they really welcomed us in. I think the first table read, when we sat there together, and you look around, and you see legends in the game that you just respect. And then for Tyler Perry to step up and be like, “Hey, all you young guys, I chose you and you for these reasons. Go do your thing.”

Was there something you learned from one of your castmates that you took with you?

Everett Osborne: Taraji affirmed something that I already stand by. We had a conversation and she was just like, “My advice that I would give you is to don’t look to the left or to the right. Do the work. Keep getting better at your craft. Don’t worry about cost sheets, what number you are on there. Don’t worry about your star meters. Don’t worry about none of that. Be committed to the work and you’re going to be just fine.” I think that’s something that I’ve always stood on, stood by. And I just feel like hearing her say that and seeing her work, working alongside of her, respecting her work, and then getting those words, it was just affirmation for me to keep doing what I’m doing.

Would you be interested in seeing a storyline focused on this next generation of Why Did I Get Married?

Everett Osborne: Like I said, I’m a lover at heart. I love this project. I love this franchise. So of course I’m all in. There’s so many ways it can go. There’s so many things at play. But if I could stand up and be a steward of story for love for our people, even if it’s ugly, even if it’s not normal, I’m all in.

You’ve worked with Tyler Perry and now you’re entering 50 Cent’s Power universe. What does it feel like to move between these different worlds?

Everett Osborne: I grew up, I’ll never forget, I was watching that for a minute. So just to be a part of it, I’ve been a fan of 50 Cent, just as an artist, as a business mogul, forever. So just to be in that world, Courtney Kemp, Sasha Penn, just to see how they’re really putting the pen to the pavement with that, it was great to be a part of it. It’s a completely different world than we just got out of. We was just in the Why Did I Get Married? franchise. Before that, I did Sweetwater, which is historical weight of the first Black NBA player. So just to kind of hop from different worlds and expand my toolbox, for me, my artistry is a gift. I’m looking forward to people seeing that, too.

Check out the full interview.