My Cup Is Full Podcast

Friendship, fallout, and flirting. I catch up with Zainab Johnson to talk about our two-year split and the reconnection that followed. She also weighs in on Sydney — flirtatious, charming, and apparently easy to bag. Tune in for laughs and honest conversation. PLEASE MAKE SURE TO CHECK OUT: Sydneyisfunny.lol for updated tickets to my comedy shows.

Season 2 of My Cup Is Full is officially here! After taking some time away, I’m back behind the mic and ready to get back in the swing of things. In this episode, I talk about the layoff, what life has been like during the break, and why it feels good to return and reconnect with y’all. I’m grateful to be back doing what I love. If you rock with the show, make sure you follow, subscribe, and share...

In this episode of My Cup is Full, Sydney Castillo sits down with his close friend and fellow comedian James Davis for a conversation filled with honesty, reflection, and gratitude. Together, they revisit the early days of chasing comedy in Los Angeles, their first writing gigs, and the milestones of creating their debut specials. Beyond the career highlights, Sydney and James share the story of a...

In this deeply personal episode of My Cup is Full, Sydney Castillo continues to bare his soul as he opens up about the loss of his mother. Raw, vulnerable, and honest, Sydney shares what it feels like to navigate grief in real time without a roadmap, without all the answers, and with the courage to ask for guidance. This conversation is an invitation for anyone walking through loss to reflect, con...

In this episode of My Cup is Full, Sydney sits down with his close friend and fellow comedian, Granville. The two share laughs and real talk as they reflect on their friendship, the challenges of navigating trauma and grief, and Granville’s journey toward opening up and receiving love from the people around him. It’s a heartfelt conversation about brotherhood, healing, and the power of letting you...

In this solo episode, Sydney opens up about his recent absence and shares the deeply personal journey of losing his mother. With honesty and vulnerability, he reflects on grief, healing, and the ways this loss has shaped his perspective on life, love, and comedy. This episode is a heartfelt check-in with his audience, offering both transparency and connection during a difficult time.

In this episode of My Cup Is Full, Sydney Castillo sits down with the multi-talented Les—author, creative powerhouse, and undeniable force in entertainment. They dive into Leslie’s unconventional path, from the hustle behind the scenes to the moments that tested (and built) his resilience. Les opens up about breaking barriers, staying grounded in a cutthroat industry, and trusting the process even...

In this episode of My Cup Is Full, Sydney Castillo kicks it with actor, comedian, and all-around hustler Justin Hires! The two chop it up about Justin’s early days in stand-up, how he broke into the industry, and what it really takes to make it in Hollywood. From wild audition stories to the grind behind the scenes, Justin keeps it all the way real. If you're chasing a dream, or just love a go...

On this episode of MY CUP IS FULL, Sydney sits down with his long-time friend and comedian Trey Moe to talk about his relationship with a puppet (Keisha Jones), his YouTube hustle, brand building, and the grind behind the spotlight. From opening for Sydney to planning his own tour, Trey shares the real behind-the-scenes journey. This one’s for the creators chasing more.

In today’s powerful and heartfelt episode, Sydney opens up like never before. With the release of his brand-new comedy special dropping today, he shares the journey behind the laughter — the grind, the pressure, and the passion that went into making it happen. But this episode isn’t just about comedy — it’s personal. Sydney gets vulnerable about the ongoing health challenges his mom is facing and...

15 years of friendship, comedy, and calling each other out! On this episode of The My Cup Is Full Podcast, host Sydney Castillo sits down with his longtime homie, comedian DC Ervin. They dive into everything—from Sydney being a ‘charming asshole’ to DC’s wild journey of having two kids as a teenager while chasing his comedy dreams. Plus, DC puts Sydney on blast for not backing up the other comedia...

On this episode of My Cup Is Full, I had the pleasure of sitting down with my good friend, the incredibly talented, Affion Crockett. From his early days in a dance group to hitting the stage on Def Comedy Jam, to working alongside the legendary Bernie Mac, Affion’s journey in comedy is nothing short of inspiring. With 41 films under his belt, he’s cemented his place in the industry—not just as a c...

In this episode of My Cup is Full, Sydney Castillo sits down with longtime friend and fellow comedian Isiah Kelly for a conversation full of laughs, memories, and real talk about the comedy grind. Growing up in the game, Isaiah was sharpening his craft from a young age under the guidance of his iconic father—so much so that at one point, he became the family’s breadwinner. Sydney and Isaiah share...

Welcome to Season 2 of My Cup is Full! Sydney Castillo kicks off the new year by bringing the laughs, love, and real talk with his first guest, the fabulous Tacarra Williams! Longtime friends, Sydney and Tacarra dive deep into their personal journeys, starting with a heartfelt surprise: Tacarra acknowledges Sydney's dream of fatherhood by giving him the next best thing—the honor of being her y...

Welcome to 2025 with My Cup is Full! In this heartfelt episode, host Sydney Castillo takes a moment to reflect on the incredible journey of the podcast that started in July 2024 and has exceeded all his expectations. Sydney shares his gratitude for the support of his listeners, who have made this platform a space for honesty, growth, and laughter. This episode dives deep into how the podcast has b...

In this powerful follow-up episode of *My Cup Is Full*, Sydney Castillo and Chase Anthony continue their heartfelt and hilarious conversation, diving even deeper into Chase’s journey of triumph and self-discovery. Chase reflects on the pivotal moment his face graced a billboard—a symbol of how far he’s come from his humble beginnings—and shares how surreal it felt to see a dream realized. The epis...

In this heartfelt and hilarious episode of My Cup Is Full, host Sydney Castillo sits down with comedian and actor Chase Anthony for an inspiring conversation about resilience, growth, and dreams. Chase opens up about his early days of struggle—living broke but full of ambition—and the life-changing opportunity to learn from the legendary Sinbad. Together, they dive into Chase’s childhood, reflecti...

In this episode of My Cup is Full, comedian and host Sydney Castillo sits down with rapper-comedian Southside Vic for a raw and authentic conversation about the journey to "making it." These two Texas natives unpack the meaning of success, the expectations of happiness that come with it, and the surprising reality that "making it" doesn’t always feel the way you’d expect. The d...

In this episode of My Cup is Full, comedian Sydney Castillo sits down with the unstoppable Eva Evans to talk about laughter, resilience, and the art of balancing life’s challenges. Together, they dive into stories of navigating past traumas and finding the humor within, as well as Eva’s dual life—superwoman by day, bad-ass comedian by night. From gut-busting laughs to real moments, they explore ho...

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 l...

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 t...

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 cha...

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...

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. But that’s not all, fam! Sydney’s got BIG news—his Patreon drops on **October 15th**! 🍿 You’ll get exclusive content, sneak peeks, and maybe even the bloopers that didn’t make it into the...

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...