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: @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 Producer: @miss.taylorrrr Follow Southside Vic on Instagram: https://www.instagram.com/victorpopejr/ Fort Worth Tix 11/29-11/30: https://fortworth.blcomedy.com/shows/sydney-castillo-live-in-fort-worth

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 life—superwoman by day, bad-ass comedian by night. From gut-busting laughs to real moments, they explore how comedy can transform pain into punchlines. Join them for a revealing conversation on healing through humor, the grind of day jobs, and the magic of the stage. Get ready to laugh, reflect, and be inspired by these two powerhouse comics! 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 Eva on Instagram and on YouTube: @evaevanscomedy Follow her podcast: Friendly Talk Podcast New York!!!! Brooklyn This Sunday 11/17 tix: 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

Ladies and Gentlemen, get your tissues ready! 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, 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. 🎟️ Chicago!! Sept. 15th!!! Get your tickets: peerpop.io/events/sydneycastilloliveatriddles 🛍️ Grab your "My Cup is Full" merch here! Merch Link Click https://sydneyisfunnymerch.creator-spring.com 🛍️ Grab your Tix for One Hour Stand Up Special in LA 9/21 https://www.squadup.com/events/sydney-castillo Sitcom Writing Course Special: 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: @SydneyCastillo (https://www.instagram.com/SydneyCastillo) Twitter: @SydneyCastillo (https://twitter.com/SydneyCastillo) Facebook: Sydney Castillo Comedy (https://www.facebook.com/SydneyCastilloComedy) Executive Producer: @sydneyisfunny ( Music by: @iamdoboy (https://www.instagram.com/iamdoboy) Follow Chris Randle IG: Reallydopename

THE AUDIO WILL FIX ITSELF AROUND 8 MIN. WE APOLOGIZE. 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. 🎟️ Get your tickets for September 28th in Dallas at ...........https://www.prekindle.com/find-tickets/id/-2853509351728169779?0&queueittoken=e_prekindle~q_f12fe4dd-e3db-40ba-8acd-93eac7b4c952~ts_1727299081~ce_true~rt_safetynet~h_5157ece6c7a4aabfbe98f0af1305826a5d817d1bf0ce20e4343c0e3502691a7c 🛍️ Grab your "My Cup is Full" merch here! Click the link for more info on the writing course: Instagram Link 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: @iamdoboy

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! Prepare for a wild ride of dating confessions, real talk, and Sydney’s endless quest to become the world’s most dedicated husband… once he figures out how to sit down! 🎟️ Get your tickets for September 28th in Dallas at (https://www.prekindle.com/find-tickets/id/-2853509351728169779?0&queueittoken=e_prekindle~q_f1fda0d8-c247-4431-b00a-34ecebf3ac15~ts_1727423982~ce_true~rt_safetynet~h_fa396a879e32310f89c0a262d8e6337600343fc62bb43c39f658570e926075ae) 🛍️ Grab your "My Cup is Full" merch here! 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

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

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/

CP 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 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