Grammy nominated artist Wale joins Not My Best Moment to talk about the setbacks that shaped his journey. From getting cut from the football team to navigating industry challenges like his debut album being under shipped, Wale shares the moments that tested him and how he pushed forward.

Kev and Wale also discuss his creative process, industry relationships and the inspiration behind his latest album everything is a lot.

A powerful reminder that setbacks are often the beginning of something greater.

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KevOnStage hits Radio Row at the Super Bowl and connects with an incredible lineup of guests. Former WWE Champion Big E talks about his new series The Evaluation, Shaun Alexander reflects on his football career and what he’s working on now, and James Harrison and Joe Haden trade stories about football memories—and why they’re still hitting the gym, even at Radio Row.

Von Miller also stops by to talk about being the best teammate possible and his latest venture, Greener Pastures Chicken.

This episode is a little different from our usual format, but we had a great time at Radio Row and hope you enjoy the ride.

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Kev talks with Emmy-winning comedian, writer, producer, and creator Robin Thede for a funny, sharp, and honest conversation about comedy, leadership, and trusting your voice. Robin breaks down her journey through stand-up, sketch, and television, including what it really takes to run a writers’ room and still stay funny.

The two dive into the realities of comedy, embarrassing moments, rewriting, navigating egos, and learning how to move through spaces where being funny isn’t always enough. Robin shares stories from her path to creating A Black Lady Sketch Show, the challenge of juggling multiple roles at once, and why confidence and humor go hand in hand.

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Kev sits down with WNBA champions and comedy duo Syd and TP aka Sydney Colson and Theresa Plaisance for a hilarious and honest conversation about life beyond basketball. The three talk about showing your true personality, dealing with injuries, and learning how to laugh at yourself when the playing days may be numbered.

Syd and TP bring their trademark humor as they swap stories about toxic locker rooms, the realities of being a professional athlete, and always finding a way to have a good time. The conversation also touches on navigating hard moments with a positive attitude, building strong relationships with teammates, and finding joy in new lanes without overthinking everything.

It’s a funny, relaxed episode full of laughs, real talk, and reminders that basketball doesn’t have to be that serious.

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Kev talks with bestselling author, speaker, and cultural critic Luvvie Ajayi Jones about trusting God, walking in purpose, and having the courage to use your voice, even when it costs you. Luvvie opens up about stepping out on faith, betting on herself, and the spiritual grounding that allows her to speak truth without fear or compromise.

The two dive into obedience, discernment, and the discipline it takes to stay aligned with your calling while navigating criticism and public pressure. Luvvie reflects on how faith has shaped her leadership, writing, and decision-making and why conviction matters more than comfort.

Along the way, there’s humor, honesty, and powerful perspective on what it means to stand firm, trust God’s timing, and move boldly in purpose.

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Kev talks with Grammy-nominated singer, songwriter, and performer Durand Bernarr about self-belief, artistic freedom, and carving out your own lane in music. Durand opens up about finding his voice, navigating the pressure to fit industry expectations, and learning to fully embrace who he is onstage and off.

The two dive into confidence, vulnerability, and the importance of trusting your instincts as a creative. Durand reflects on the journey from background vocalist to solo artist, the lessons learned along the way, and what it takes to stay grounded while putting your authentic self in the spotlight.

There’s humor, honesty, and powerful insight into why owning your individuality and protecting your joy is the real key to longevity.

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Kev talks with actress, comedian, and author Yvonne Orji about patience, purpose, and trusting God’s timing in an industry that rewards speed over substance. Yvonne opens up about pursuing comedy while holding firm to her faith, turning down opportunities that didn’t align with her values, and enduring years of uncertainty before her breakthrough on Insecure.

The two dive into the pressure to compromise, the fear of being “left behind,” and the discipline required to keep showing up when success feels delayed. Yvonne shares how obedience, preparation, and belief carried her through seasons of waiting—and why the journey shaped her far more than the destination.

Along the way, there’s laughter, honesty, and powerful perspective on what it really means to trust the process without losing yourself.

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Kev talks with comedian and actor Tony Baker about the long, often unseen road to success in entertainment. Tony shares the hilarious story of failing seventh grade, opens up about the devastation of a network pilot not getting picked up, and the heartbreak of not advancing on Last Comic Standing. The two dive deep into the realities of stand-up comedy, scraping by on low-paying shows, bombing onstage, rebuilding confidence, and learning how to survive when the industry feels completely out of your control. Tony explains how his faith, love for stand-up, and relentless work ethic helped him push through years of rejection, divorce, and financial uncertainty.

Along the way, there are plenty of laugh-out-loud stories about brutal crowd reactions, unforgettable bombing moments, and why loving the craft, not the spotlight, is what ultimately kept Tony going.

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