Episodes
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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 apparently easy to bag. Tune in for laughs and honest conversation.PLEASE MAKE SURE TO CHECK OUT:...
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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 has been like during the break, and why it feels good to return and reconnect with y’all.I’m…
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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 revisit the early days of chasing comedy in Los Angeles, their first writing gigs, and the…
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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 like to navigate grief in real time without a roadmap, without all the answers, and with the courage…
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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 navigating trauma and grief, and Granville’s journey toward opening up and receiving love from the...
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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 this loss has shaped his perspective on life, love, and comedy. This episode is a heartfelt...
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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 path, from the hustle behind the scenes to the moments that tested (and built) his resilience. Les...
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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 industry, and what it really takes to make it in Hollywood. From wild audition stories to the…
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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, and the grind behind the spotlight. From opening for Sydney to planning his own tour, Trey shares…
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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, the pressure, and the passion that went into making it happen.But this episode isn’t just about...
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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 everything—from Sydney being a ‘charming asshole’ to DC’s wild journey of having two kids as a...
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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 Comedy Jam, to working alongside the legendary Bernie Mac, Affion’s journey in comedy is nothing...
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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. Growing up in the game, Isaiah was sharpening his craft from a young age under the guidance of his...
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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 and Tacarra dive deep into their personal journeys, starting with a heartfelt surprise: Tacarra...
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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 his expectations. Sydney shares his gratitude for the support of his listeners, who have made this...
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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 self-discovery. Chase reflects on the pivotal moment his face graced a billboard—a symbol of how…
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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. Chase opens up about his early days of struggle—living broke but full of ambition—and the…
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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 Texas natives unpack the meaning of success, the expectations of happiness that come with it, and the...
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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 dive into stories of navigating past traumas and finding the humor within, as well as Eva’s dual...
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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 family. They dive deep into the sacrifices that come with the grind of being successful comedians—like...
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LET'S MEET TAYLOR/ KISSING BANDIT/ PG COUNTY LEGEND/SHOOT YO SHOT
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....
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Detroit's own Comedian CP/ Ex roommate/ I’m a Bear, he’s a Rabbit!!!!
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...
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"Flowers for a Fighter: Honoring JSnow's Journey"
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…
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Dropping A Podcast to Dropping a Special
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**!...
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I'm Sitting Down Momma...My Cup Is Full w/ Tacarra Williams Ep 13
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…
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Are Sydney and Taccara Dating? | My Cup Is Full w/ Tacarra Ep 12
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...
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My Father Was Murdered??? My Cup Is Full w/ Chris Randle- Ep 11
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...
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I'm Giving Flowers Feat. Tyler Chronicles | My Cup Is Full w/ Tyler Chronicles - Ep 10
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…
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I Was Married for 20 Minutes | Withholding Sex? | My Cup Is Full w/ Tamara Williams Ep 9
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…
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Meeting Tony Rock & "My Job Is To Knock You Out" | My Cup Is Full - Ep 8
You asked and we delivered! Welcome back to the "My Cup is Full" podcast with your host, Sydney Castillo! In this weeks episode, Sydney takes us behind the scenes of his life on the road with the legendary Tony Rock! Sydney shares unforgettable stories from their comedy tours, including the…
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"May 30th, 2017" ...The Day I My Anxiety | My Cup Is Full - Ep 7
Another week, another amazing episode of "My Cup is Full" podcast with your host, Sydney Castillo! This week, Sydney opens up about why his cup is full, sharing an intimate look into his mind and heart. From the loss of the two most important men in his life to his mother’s courageous battle...
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Sacrificing Cats in the Name of Love -- Bonus Episode w/ Dulce Sloan - Ep 6
Get ready for extra laughs in this bonus episode of "My Cup is Full"! Host Sydney Castillo and special guest Dulce Sloan serve up an unfiltered conversation about dating, relationships, and the comedy life. From first date etiquette to equally yoked partnerships, they dive deep into personal...
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Scam Chronicles: Hidden Pregnancy to Costa Rica Scam w/ Dulce Sloan | My Cup Is Full Ep 5
Welcome back to another thrilling episode of My Cup is Full Podcast with your host, Sydney Castillo! In this episode, we're joined by special guest, actress and stand-up comedian Dulce Sloan, as we dive deep into the murky world of scams. From outrageous fake pregnancies to elaborate Costa Rica...
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From Waiting Tables to a Comedy Career | My Cup is Full Ep 4
In this episode of My Cup is Full, host Sydney Castillo takes us through his incredible journey from the hustle of waiting tables to making it big in the comedy scene. Sydney dives into his early experiences, including his first stand-up gig discovered via Myspace, performing on HBO’s Bad Boys of...
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Who Stole From My Momma!!??? My Cup is Full w/ Courtney Bee & DWFLAME | Ep 3
Join Comedian Sydney Castillo and his hilarious guests, Comedian Courtney Bee @therealcourtneybee and Recording Artist @DWFLAME as they dive into a wild tale of family drama, stolen money, and unexpected trips to Paris. In this episode of "My Cup is Full," Sydney shares a jaw-dropping story about...
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Sifting Through the Rubble | My Cup is Full w/ Tacarra Williams | Ep 2
We're back with Part 2 of our explosive premiere episode of "MY CUP IS FULL"! After the shocking reveal of what happened to my apartment, Tacarra Williams (@tacarracomedy) and I are diving deep into your burning questions. In this episode, we're tackling all the "what ifs," "how comes," and "why...
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She Did WHAT to Your Apartment?! | My Cup is Full w/ Tacarra Williams Ep 1
Welcome to "MY CUP IS FULL" - a new podcast where I, Sydney Castillo, share real stories from my life that explain why my cup is overflowing! In this explosive first episode, I'm joined by the hilarious @tacarracomedy as we dive into a dating disaster that ended with my place getting smashed to...
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About this show
Comedian Sydney Castillo opens up about all things that give him anxiety.
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