Shows
My Cup Is Full PodcastJUST NESH MADE EVERYBODY CRYIn 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 th...
2024-11-0741 minMy Cup Is Full PodcastLET'S MEET TAYLOR/ KISSING BANDIT/ PG COUNTY LEGEND/SHOOT YO SHOTIn 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.

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2024-11-0730 minMy Cup Is Full PodcastDetroit'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 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.
Sydney shares the story of their friend...
2024-11-0746 minMy Cup Is Full Podcast"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 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 th...
2024-11-0757 minMy Cup Is Full PodcastDropping A Podcast to Dropping a SpecialThis 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 special (you know, the real gold!). Don’t miss out!
It’s time to fill your cup and sip on these stories. 🍵 Tune in and laugh along with Sydney as he keeps it real (and...
2024-11-0726 minMy Cup Is Full PodcastI'm Sitting Down Momma...My Cup Is Full w/ Tacarra Williams Ep 13In 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!
2024-09-2739 minMy Cup Is Full PodcastAre Sydney and Taccara Dating? | My Cup Is Full w/ Tacarra Ep 12In 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.
The two also share the deeply personal story that sparked their friendship—the tragic death of Sydney’s best friend and Tacarra’s ex-husband. In the midst of grief, they found a unique bond that has helped them heal, grow, and continue...
2024-09-2539 minMy Cup Is Full PodcastMy Father Was Murdered??? My Cup Is Full w/ Chris Randle- Ep 11This 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.
Together, they explore the profound impact of having a...
2024-09-041h 31My Cup Is Full PodcastI'm Giving Flowers Feat. Tyler Chronicles | My Cup Is Full w/ Tyler Chronicles - Ep 10On 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 me...
2024-08-2758 minMy Cup Is Full PodcastI Was Married for 20 Minutes | Withholding Sex? | My Cup Is Full w/ Tamara Williams Ep 9In 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.
2024-08-2141 minMy Cup Is Full PodcastMeeting Tony Rock & "My Job Is To Knock You Out" | My Cup Is Full - Ep 8You 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 highs, the laughs, and the lessons learned along the way.
But it’s not all smooth sailing! Sydney opens up about the first time he bombed during a comedy show in Miami—an experience every comedian faces at some point. Hear how he bounced back, what he learned from the...
2024-08-1741 minMy Cup Is Full Podcast"May 30th, 2017" ...The Day I My Anxiety | My Cup Is Full - Ep 7Another 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 against cancer twice all while maintaining and chasing his comedy career. Sydney discusses how he managed to keep his audience laughing through the toughest years of his life.
Sydney highlights the journey that has shaped him, emphasizing the crucial role of therapy, support from friends, se...
2024-08-0652 minMy Cup Is Full PodcastSacrificing Cats in the Name of Love -- Bonus Episode w/ Dulce Sloan - Ep 6Get 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 experiences and hilarious anecdotes. Hear their takes on spirituality in relationships, career-life balance, and the eternal debate of cats vs. dogs.
This bonus episode is packed with raw honesty, unexpected twists, and the kind of real talk that'll have you cackling. Whether you're navigating the dating scene or just need a good...
2024-08-0227 minMy Cup Is Full PodcastScam Chronicles: Hidden Pregnancy to Costa Rica Scam w/ Dulce Sloan | My Cup Is Full Ep 5Welcome 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 scams, Sydney and Dulce share jaw-dropping stories and valuable insights to help you stay vigilant. Don't miss out on these wild tales that will leave you questioning everything!
🎟️ Get your tickets for August 22nd in Atlanta at Uptown Comedy Corner! https://www.eventbrite.com/e/uptown-comedy-corner-presents-sydney-castillo-live-1-night-only-tickets-920479949307
🛍️ Grab your My Cup is Ful...
2024-07-3145 minMy Cup Is Full PodcastFrom Waiting Tables to a Comedy Career | My Cup is Full Ep 4In 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 Comedy, and balancing day jobs while pursuing his dreams. Listen in as he recounts working with legendary comedians like Ian Edwards, his time on BET shows, and his big win on TBS’s Funniest Wins. This episode is packed with humor, perseverance, and invaluable insights into the worl...
2024-07-2349 minMy Cup Is Full PodcastWho Stole From My Momma!!??? My Cup is Full w/ Courtney Bee & DWFLAME | Ep 3Join 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 $50,000 disappearing from his mom's account, leading to a rollercoaster of emotions, petty revenge, and life lessons. From banning haircuts to resisting the urge for payback, this episode is packed with laughter, shocking revelations, and heartfelt moments.
Discover how Sydney navigates family betrayal while keeping his comedic spirit alive. Don't miss this captivating bl...
2024-07-1043 minMy Cup Is Full PodcastSifting Through the Rubble | My Cup is Full w/ Tacarra Williams | Ep 2We'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 didn't yous" you've been dying to ask. We're getting into:
* The red flags I missed (and why)
* What happened after the destruction
* How this wild experience changed my approach to relationships
* Tacarra's unfiltered advice on avoiding similar situations
Plus, we're sharing some never-before-heard details that will have your jaw on...
2024-07-0239 minMy Cup Is Full PodcastShe Did WHAT to Your Apartment?! | My Cup is Full w/ Tacarra Williams Ep 1Welcome 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 smithereens! 😤 You won't believe this wild tale of relationship chaos.
This is just the beginning - tell a friend and subscribe for more unbelievable stories that'll have you laughing, cringing, and maybe even learning a thing or two about life and love.
Pro...
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