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IS SYDNEY EASILY BAGGABLE?!? W/ ZAINAB JOHNSON
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…
WELCOME BACK: TOOK SOME TIME TO MYSELF | READY TO GET BACK TO WORK
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…
Brother's In Comedy | My Cup Is Full w/ James Davis | Ep. 36
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…
I NEED TIPS: Navigating Grief In Real TIme | My Cup Is Full | Ep. 35
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…
Learning To Open Up | My Cup Is Full w/ Granville | Ep. 34
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…
My Mom Passed | My Cup Is Empty | Ep. 33
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…
IF I WERE YOUR HOMIE | My Cup Is Full W/ Les | Ep. 32
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…
I Can Do Anything | My Cup is Full w/ Justin Hires | Ep. 31
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…
In a Relationship With a PUPPET ft. Trey Moe
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,…
COMEDY SPECIAL/MOM/PUSHING THRU W/ SYDNEY CASTILLO Ep. 29
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,…
Charmingly Rude: The Nice A-Hole w/ DC Ervin
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…
Hustle N Humor | My Cup is Full w/ Affion Crockett | Ep. 26
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…
A Comedy Legend Was Born | My Cup is Full w/ Isiah Kelly | Ep. 25
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.…
Saying YES To Love | My Cup is Full w/ Tacarra Williams | Ep. 24
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…
New Year, Full Cup: Reflection, Gratitude, and Growth | My Cup is Full | Ep. 23
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…
From Empty fridges to BIGGER things | My Cup is Full w/ Chase Anthony | Ep. 22
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…
S1E21 Uncle Dad SINBAD | My Cup is Full w/ Chase Anthony | Ep. 21
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.…
S1E20 The Reality Of Making It | My Cup is Full w/ Southside Vic | Ep. 20
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…
Brooklyn's Finest | My Cup is Full w/ Eva Evans | Ep. 19
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…
JUST NESH MADE EVERYBODY CRY
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…
Frequently Asked Questions
My Cup Is Full Podcast has published 38 episodes since June 2024, covering topics in Comedy.
My Cup Is Full Podcast is currently dormant with new episodes daily. Average episode length is 44m.
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