My Cup Is Full Podcast
Episodes
IS SYDNEY EASILY BAGGABLE?!? W/ ZAINAB JOHNSON
18 Mar 2026
Contributed by Lukas
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...
WELCOME BACK: TOOK SOME TIME TO MYSELF | READY TO GET BACK TO WORK
14 Mar 2026
Contributed by Lukas
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...
Brother's In Comedy | My Cup Is Full w/ James Davis | Ep. 36
14 Mar 2026
Contributed by Lukas
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 hone...
I NEED TIPS: Navigating Grief In Real TIme | My Cup Is Full | Ep. 35
14 Mar 2026
Contributed by Lukas
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, vulner...
Learning To Open Up | My Cup Is Full w/ Granville | Ep. 34
14 Mar 2026
Contributed by Lukas
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 r...
My Mom Passed | My Cup Is Empty | Ep. 33
14 Mar 2026
Contributed by Lukas
In this solo episode, Sydney opens up about his recent absence and shares the deeply personal journey of losing his mother. With honesty and vulnerabi...
IF I WERE YOUR HOMIE | My Cup Is Full W/ Les | Ep. 32
14 Mar 2026
Contributed by Lukas
In this episode of My Cup Is Full, Sydney Castillo sits down with the multi-talented Les—author, creative powerhouse, and undeniable force in entert...
I Can Do Anything | My Cup is Full w/ Justin Hires | Ep. 31
14 Mar 2026
Contributed by Lukas
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...
In a Relationship With a PUPPET ft. Trey Moe
14 Mar 2026
Contributed by Lukas
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 (Keis...
COMEDY SPECIAL/MOM/PUSHING THRU W/ SYDNEY CASTILLO Ep. 29
14 Mar 2026
Contributed by Lukas
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 sh...
Charmingly Rude: The Nice A-Hole w/ DC Ervin
14 Mar 2026
Contributed by Lukas
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 lon...
Hustle N Humor | My Cup is Full w/ Affion Crockett | Ep. 26
14 Mar 2026
Contributed by Lukas
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 da...
A Comedy Legend Was Born | My Cup is Full w/ Isiah Kelly | Ep. 25
14 Mar 2026
Contributed by Lukas
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, m...
Saying YES To Love | My Cup is Full w/ Tacarra Williams | Ep. 24
14 Mar 2026
Contributed by Lukas
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 fa...
New Year, Full Cup: Reflection, Gratitude, and Growth | My Cup is Full | Ep. 23
14 Mar 2026
Contributed by Lukas
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 podcas...
From Empty fridges to BIGGER things | My Cup is Full w/ Chase Anthony | Ep. 22
14 Mar 2026
Contributed by Lukas
In this powerful follow-up episode of *My Cup Is Full*, Sydney Castillo and Chase Anthony continue their heartfelt and hilarious conversation, diving ...
Uncle Dad SINBAD | My Cup is Full w/ Chase Anthony | Ep. 21
14 Mar 2026
Contributed by Lukas
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 conve...
The Reality Of Making It | My Cup is Full w/ Southside Vic | Ep. 20
14 Mar 2026
Contributed by Lukas
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...
Brooklyn's Finest | My Cup is Full w/ Eva Evans | Ep. 19
14 Mar 2026
Contributed by Lukas
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 o...
JUST NESH MADE EVERYBODY CRY
07 Nov 2024
Contributed by Lukas
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 ...
LET'S MEET TAYLOR/ KISSING BANDIT/ PG COUNTY LEGEND/SHOOT YO SHOT
07 Nov 2024
Contributed by Lukas
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 ...
Detroit's own Comedian CP/ Ex roommate/ I’m a Bear, he’s a Rabbit!!!!
07 Nov 2024
Contributed by Lukas
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 o...
"Flowers for a Fighter: Honoring JSnow's Journey"
07 Nov 2024
Contributed by Lukas
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...
Dropping A Podcast to Dropping a Special
07 Nov 2024
Contributed by Lukas
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 ...
I'm Sitting Down Momma...My Cup Is Full w/ Tacarra Williams Ep 13
27 Sep 2024
Contributed by Lukas
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 t...
Are Sydney and Taccara Dating? | My Cup Is Full w/ Tacarra Ep 12
25 Sep 2024
Contributed by Lukas
In this heartfelt episode of My Cup is Full, host Sydney Castillo sits down with fellow comedian *Tacarra Williams* for a candid conversation about th...
My Father Was Murdered??? My Cup Is Full w/ Chris Randle- Ep 11
04 Sep 2024
Contributed by Lukas
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 j...
I'm Giving Flowers Feat. Tyler Chronicles | My Cup Is Full w/ Tyler Chronicles - Ep 10
27 Aug 2024
Contributed by Lukas
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 heartfel...
I Was Married for 20 Minutes | Withholding Sex? | My Cup Is Full w/ Tamara Williams Ep 9
21 Aug 2024
Contributed by Lukas
In this week’s episode, Sydney is joined by guest Tacarra Williams as they dive into discussions on divorce, compatibility, and dating after divorce...
Meeting Tony Rock & "My Job Is To Knock You Out" | My Cup Is Full - Ep 8
17 Aug 2024
Contributed by Lukas
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 behi...
"May 30th, 2017" ...The Day I My Anxiety | My Cup Is Full - Ep 7
06 Aug 2024
Contributed by Lukas
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 f...
Sacrificing Cats in the Name of Love -- Bonus Episode w/ Dulce Sloan - Ep 6
02 Aug 2024
Contributed by Lukas
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 conver...
Scam Chronicles: Hidden Pregnancy to Costa Rica Scam w/ Dulce Sloan | My Cup Is Full Ep 5
31 Jul 2024
Contributed by Lukas
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, a...
From Waiting Tables to a Comedy Career | My Cup is Full Ep 4
23 Jul 2024
Contributed by Lukas
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 ...
Who Stole From My Momma!!??? My Cup is Full w/ Courtney Bee & DWFLAME | Ep 3
09 Jul 2024
Contributed by Lukas
Join Comedian Sydney Castillo and his hilarious guests, Comedian Courtney Bee @therealcourtneybee and Recording Artist @DWFLAME as they dive into ...
Sifting Through the Rubble | My Cup is Full w/ Tacarra Williams | Ep 2
02 Jul 2024
Contributed by Lukas
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 Will...
She Did WHAT to Your Apartment?! | My Cup is Full w/ Tacarra Williams Ep 1
01 Jul 2024
Contributed by Lukas
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 ...
My Cup Is Full Podcast Trailer
25 Jun 2024
Contributed by Lukas
Subscribe!!! Follow me @sydneyisfunny