My Cup Is Full Podcast

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 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!

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 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 to make others laugh along the way. Tune in for a raw, emotional, and surprisingly uplifting conversation about life, loss, and the power of comedy.

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 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 strong support system, particularly when coping with the loss of Black fathers. They emphasize the importance of leaning on one another during life’s toughest moments. Their discussion also delves into the unique challenges of balancing a career in entertainment while navigating personal struggles, offering a candid and moving look at the importance of brotherhood, vulnerability, and emotional resilience. Tune in for an episode filled with laughter, deep reflections, and a powerful reminder of the bonds that sustain us.

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 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 mental health. Their candid discussion sheds light on the importance of support, understanding, and the strength it takes to thrive both personally and professionally. Don't miss this powerful episode filled with laughter, vulnerability, and valuable insights.

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 conversation that explores the challenges and growth that come with navigating relationships and dating in the wake of divorce.

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 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 experience, and why it made him a stronger performer.

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 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, self-trust, and the importance of allowing himself to grieve. He shares his story of perseverance, faith in God, and the unwavering determination to stay the course

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 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 laugh, this extra serving of "My Cup is Full" delivers the goods! 🎟️ 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 Full merch here! https://sydneyisfunnymerch.creator-spring.com/ Click the link for more info on writing course: https://l.instagram.com/?u=https%3A%2F%2Flinktr.ee%2Fsydneyisfunny&e=AT2DD-V3gFv7lXTw9Pl-NpH1Nm8k4MJ6mub6Z-29t9vanNvKBmWBP47TK6--kCMbq6i260lSV646khD0EcZxSjczMOfCfvf6_8fkMLfRlXVK7M97kg66 Don't forget to like, subscribe, and hit the notification bell to stay updated on all our episodes. Follow Sydney Castillo: Instagram: @SydneyCastillo Twitter: @SydneyCastillo Facebook: Sydney Castillo Comedy .......... Executive Producer: @sydneyisfunny Producer: @miss.taylorrrr Music by: @IamDoBoyTV Editing: @CecilyJamelia

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 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 Full merch here! https://sydneyisfunnymerch.creator-spring.com/ Click the link for more info on writing course: https://l.instagram.com/?u=https%3A%2F%2Flinktr.ee%2Fsydneyisfunny&e=AT2DD-V3gFv7lXTw9Pl-NpH1Nm8k4MJ6mub6Z-29t9vanNvKBmWBP47TK6--kCMbq6i260lSV646khD0EcZxSjczMOfCfvf6_8fkMLfRlXVK7M97kg66 Don't forget to like, subscribe, and hit the notification bell to stay updated on all our episodes. Follow Sydney Castillo: Instagram: @SydneyCastillo Twitter: @SydneyCastillo Facebook: Sydney Castillo Comedy .......... Executive Producer: @sydneyisfunny Producer: @miss.taylorrrr Music by: @IamDoBoyTV Editing: @CecilyJamelia

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 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 world of comedy. Show Highlights: Sydney's transition from modeling to stand-up comedy The bittersweet reality of post-TV fame and waiting tables Learning the craft of comedy writing from industry veterans The emotional highs and lows of working on major award shows The pivotal moment of winning a major comedy competition Adventures in international travel and career milestones

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 $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 blend of humor and real-life drama that'll have you laughing, gasping, and maybe even calling your own family to check on your bank account! Don't forget to like, subscribe, and hit that notification bell for more unbelievable stories that'll have you saying, "At least my cup isn't that full!" Executive Producer: @sydneyisfunny Producer: @miss.taylorrrr Music by: @iamdobyy Editing:  @CecilyJamelia 

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 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 the floor. Whether you're laughing, cringing, or taking notes, this episode is packed with real talk about dating, boundaries, and learning from life's craziest moments. Don't forget to like, subscribe, and hit that notification bell for more unbelievable stories that'll have you saying, "At least my cup isn't that full!" Producer: @miss.taylorrrr Music by: @iamdobby Editing: @cecilyjamelia

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 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. Producer: @miss.taylorrrr Music by: @iamdoboy Editing: @cecilyjamelia

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

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. 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.  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 FOLLOW TAYLOR ON INSTAGRAM: @Miss.Taylorrrr

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/

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 throws your way. 🛍️ Grab your "My Cup is Full" merch here: https://www.youtube.com/redirect?event=channel_header&redir_token=QUFFLUhqbExtVEVBZUsyQVFqOEJUVVpndTlCb2tHSUpjZ3xBQ3Jtc0tsaXlrWGpHSkhfRjNqMlY0XzVhM3hYNGt1NmZCVzJPV0h4bTJUTjJpN2J0c1FrZFBleTdZVXlYcHlrRVFFRXR6WmRRRW82eDYxd1NmTGl1MHVLS2N2RW1wQ3lJcVFoY2xIMURDS25sOHJocUNwUFVWbw&q=https%3A%2F%2Fsydneyisfunnymerch.creator-spring.com Click the link for more info on the writing course: https://linktr.ee/sydneyisfunny?fbclid=PAZXh0bgNhZW0CMTEAAaZcD9rObkwYB_M2j4MwXikCZljj3kYKKpCPqwWXJ5OncD4vWES25W6ddQo_aem_GJhObVfRYh5JVri1zQyeDQ 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 J Snow: https://www.instagram.com/jsnowpro/ Follow Tyler for merch: @tylerchronicles 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 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

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