In this heartfelt and hilarious episode of *My Cup is Full*, comedian Sydney Castillo sits down with the dynamic Just Nesh for an honest conversation about the joys and struggles of comedy and family. They dive deep into the sacrifices that come with the grind of being successful comedians—like Nesh's balance as a mom and performer and Sydney's journey to one day becoming a dad himself. With raw laughs, touching insights, and a few tears, they explore the price of chasing dreams and the fulfillment that family brings. Grab a seat for an unforgettable chat that goes beyond the stage, sharing both the laughs and life lessons that come with it.

In this episode of *My Cup is Full*, Sydney Castillo invites his producer, Taylor Gang, to step out from behind the scenes and join him on camera for the first time! Together, they dive into hilarious stories about Taylor’s dating life, her latest travel adventures, and her ever-changing braids. From playful banter to real talk, Sydney and Taylor explore what it means to balance fun, love, and a touch of glamour. Get ready for laughs, friendship, and a fresh perspective as Taylor finally takes her seat in front of the mic.

CP from Detroit and Sydney Castillo have the kind of friendship that feels like a buddy cop movie—except the only thing they’re policing is each other’s jokes. From grinding through the tough days when comedy gigs barely covered gas money, to sharing the stage and laughing so hard they can’t even finish a sentence, their bond runs deep. CP’s sharp Detroit hustle meets Sydney’s laid-back, Texas charm, making for a duo that knows how to roast each other without mercy, then turn around and crack up about it.

In this heartfelt episode of *My Cup is Full*, comedian Sydney Castillo takes a moment to honor his friend and fellow comedian, J Snow. Sydney gives J Snow his well-deserved flowers, celebrating not only his incredible talent as a writer and comedian but also his resilience in continuing to create while battling sickle cell. They dive into JSnow’s journey of perseverance, his impact on comedy, and the strength it takes to thrive in the entertainment industry, despite personal challenges. Tune in for an inspiring conversation about friendship, comedy, and the courage to keep going no matter what life throws your way.

This week, Sydney Castillo’s cup runneth over with laughs as he spills the beans on his latest comedy special. 🚨 Get the behind-the-scenes scoop on his hilarious (and sometimes ridiculous) journey to get there.

In this episode of *My Cup is Full*, comedian Sydney Castillo gets real about love, dating, and his mission to become a husband—no matter how many times he says "momma" along the way. Joined by the hilarious Tacarra Williams, the two dive into Sydney’s unique (and slightly confusing) definition of "sitting down" when it comes to relationships. Spoiler: it doesn’t actually involve a chair. Tune in for belly laughs as they tackle Sydney's fears about the dating world, his overuse of pet names, and his determination to put a ring on it—one way or another!

In this heartfelt episode of My Cup is Full, host Sydney Castillo sits down with fellow comedian *Tacarra Williams* for a candid conversation about the journey of finding humor in life’s toughest moments. Sydney and Tacarra open up about the ups and downs of their careers as comedians, reflecting on the challenges, triumphs, and everything in between.

This is the dead daddy gang episode! We have an incredible episode of the “My Cup is Full" podcast with your host, Sydney Castillo, who is finally joined by his best friend and fellow comedian, Chris Randle, for a raw and heartfelt conversation about the power of friendship, especially between Black men. Sydney opens up about how Chris has been his rock through some of the darkest times, including the loss of his father. Chris, in turn, shares how his faith has been a cornerstone during his own journey through grief.

On this episode of the "My Cup is Full" podcast, host Sydney Castillo sits down with comedian and writer Tyler Chronicles for an intimate and heartfelt conversation. Sydney, who jokes that he has more friends than Chris, takes a moment to give Tyler his well-deserved flowers for being an unwavering friend during Sydney's battles with depression and anxiety—unaware that Tyler was quietly facing his own family struggles at the same time. Together, they dive into the unique challenges of navigating the entertainment industry as two Black men, balancing the demands of a fulfilling career while also wrestling with mental health. Their candid discussion sheds light on the importance of support, understanding, and the strength it takes to thrive both personally and professionally. Don't miss this powerful episode filled with laughter, vulnerability, and valuable insights.

In this week’s episode, Sydney is joined by guest Tacarra Williams as they dive into discussions on divorce, compatibility, and dating after divorce. They share personal insights and experiences on these topics, offering listeners a blend of humor and real talk. Tune in for an engaging conversation that explores the challenges and growth that come with navigating relationships and dating in the wake of divorce.