My Cup Is Full Podcast

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 short of inspiring. With 41 films under his belt, he’s cemented his place in the industry—not just as a comedic powerhouse but as one of the most genuine, hard-working, and humble guys in the game. I had to give my brother his flowers for all he’s accomplished while staying true to himself. Tune in for laughs, stories, and a deep dive into the grind behind the greatness! 🎤🔥 #AffionCrockett #ComedyLegend #RespectTheJourney #GivingFlowers”

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 acknowledges Sydney's dream of fatherhood by giving him the next best thing—the honor of being her youngest child’s godfather honoring her late ex-husband and Sydney’s great friend. From there, the duo keeps it raw and hilarious, discussing where they currently stand in the world of dating—whether it’s sitting still or putting themselves out there. They share how to approach them (yes, there’s a right way!), why they’re saying yes to love, and cherries???Pour yourself a cup of whatever fills you up, and tune in for this unforgettable season opener full of laughs, life lessons, and love.

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 far he’s come from his humble beginnings—and shares how surreal it felt to see a dream realized. The episode takes a personal turn as Chase opens up about the impact of Sydney’s unwavering friendship, crediting him as a cornerstone of support during his toughest times. In an emotional moment, Chase gets vulnerable, expressing gratitude so heartfelt it might even bring a tear to your eye (spoiler alert: it definitely brought one to his). Filled with laughter, inspiration, and a reminder of the power of true friendship, this episode will leave you uplifted and ready to chase your own dreams. Don’t miss this unforgettable conversation!Instagram: @SydneyisfunnyTwitter: @SydneyisfunnyFacebook: Sydne Don't forget to like, subscribe, and hit the notification bell to stay updated on all our episodes.Follow Sydney Castillo:Instagram: @SydneyisfunnyTwitter: @SydneyisfunnyFacebook: SydneyisfunnyExecutive Producer: @sydneyisfunny Producer: @miss.taylorrrr Chase Anthony Instagram: @Chasecomedy Ghetto Genius Store: https://www.ghettogeniusclub.comMyCupIsFull merch available rt now!!!! MeetSydneyCastillo.com

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 surprising reality that "making it" doesn’t always feel the way you’d expect. The duo gets candid about the pressures of the entertainment industry, sharing personal insights on the value of mentorship and the strength found in true friendship. With humor and heart, Sydney and Vic remind us that success isn’t just about what you achieve but the people who support you along the way. Grab a cup, sit down, and dive into this honest and thought-provoking episode.Instagram: @SydneyisfunnyTwitter: @SydneyisfunnyFacebook: Sydne Don't forget to like, subscribe, and hit the notification bell to stay updated on all our episodes.Follow Sydney Castillo:Instagram: @SydneyisfunnyTwitter: @SydneyisfunnyFacebook: SydneyisfunnyExecutive Producer: @sydneyisfunny Producer: @miss.taylorrrr Follow Southside Vic on Instagram: / victorpopejr

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 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 the stage, sharing both the laughs and life lessons that come with it. Don't forget to like, subscribe, and hit the notification bell to stay updated on all our episodes. Follow Sydney Castillo: Instagram: @Sydneyisfunny Twitter: @Sydneyisfunny Facebook: Sydne Don't forget to like, subscribe, and hit the notification bell to stay updated on all our episodes. Follow Sydney Castillo: Instagram: @Sydneyisfunny Twitter: @Sydneyisfunny Facebook: Sydneyisfunny Executive Producer: @sydneyisfunny This Friday and Saturday San Antonio Texas!!! Tix below: https://www.eventbrite.com/e/sydney-castillo-special-event-tickets-1062967377039

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 friendly rivalry and mutual respect, highlighting CP's rise to success and the bond they've formed through years of competing, collaborating, and cracking jokes. Tune in for laughs, real talk, and a celebration of CP's hustle, all while Sydney gives his longtime friend the flowers he deserves. Don't forget to like, subscribe, and hit the notification bell to stay updated on all our episodes. Follow Sydney Castillo: Instagram: @Sydneyisfunny Twitter: @Sydneyisfunny Facebook: Sydneyisfunny Executive Producer: @sydneyisfunny Producer: @miss.taylorrrr Music by: @iamdoboy CP: https://www.instagram.com/comediancp/ Upcoming Show tickets: 10/27 Greensboro, NC https://thecomedyzone.com/shows/285452 10/29 Hollywood, CA https://improv.com/hollywood/comic/sydney+castillo/ 11/3 Arlington, TX https://arlingtonmusichall.org/eventbrite-event/sydney-castillo/ 11/8 - 11/9 San Antonio, TX https://app.showslinger.com/standalone_external_events/25522?from=%2Fpromo_widget_v3%2Fcombo_widget%3Fid%3D31%26origin_url%3Dhttps%253A%252F%252Fwww-upstagecomedylounge-net.filesusr.com%252Fhtml%252Fbc6dbb_460476eedde51dab237cf59b47bbac97.html&promo_widget_v3_id=31 11/17 Brooklyn New York: https://www.stellartickets.com/o/brooklyn-art-haus--2/events/syndey-castillo-live-presented-by-the-new-york-comedy-festival/occurrences/6eed4460-84a5-4bb8-9b33-98b10881b56c 12/21 Somerville, Ma https://therockwell.org/calendar/sydney-castillo/

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**! 🍿 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 real funny)! Hollywood, CA!!! 10/29 tix right here: https://improv.com/comic/sydney+castillo/ 🛍️ Grab your "My Cup is Full" merch here! https://www.youtube.com/redirect?event=channel_header&redir_token=QUFFLUhqa0pka1Nrc3FWU3dDcnpKOWtoaFJKb0VoY3oyUXxBQ3Jtc0tuelFKT2dyVHZYRmF1M2pqeEhxRWFoOE8yTllkdUNvaXhrQzd3SXlzbGNPR0t6YXVKbTFtVUMtWVpVT0NtbldvTXEzZUViRVN2V2ROcnBUSms3aGhMNmVBY2dsa0RKb3d4QmJYZWQ4MlpQc3VZRDExdw&q=https%3A%2F%2Fsydneyisfunnymerch.creator-spring.com Click the link for more info on the writing course: https://linktr.ee/sydneyisfunny Don't forget to like, subscribe, and hit the notification bell to stay updated on all our episodes. Follow Sydney Castillo: Instagram: @Sydneyisfunny Twitter: @Sydneyisfunny Facebook: sydneyisfunny Executive Producer: @sydneyisfunny Producer: @miss.taylorrrr Music by: @iamdoboy