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 so we can keep filling these cups together.

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 friendship that has weathered both highs and lows, reminding us of the power of support, resilience, and celebrating dreams realized alongside the people who’ve been there since the beginning.

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, connect, and maybe even find a little comfort in knowing they’re not alone.

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 yourself be supported.

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 when the odds are stacked. Whether you're carving your own lane or just need a boost of inspiration, this conversation is rich with wisdom, laughs, and that signature My Cup Is Full energy.

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 good underdog story, this episode is packed with gems, laughs, and that signature My Cup Is Full energy!

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 how it’s affecting him emotionally. He reflects on how he’s been navigating the weight of caregiving, the guilt, the gratitude, and the realization that he needs to do better at managing those emotions, both for himself and for her.This one’s real, raw, and full of heart.