Sydney Castillo Wins Funniest Wins

Sydney Castillo Wins Funniest Wins


Fresh off his win on TBS’s Comedy Competition Funniest Wins, Sydney Castillo has big plans for his $100,000 cash prize, and his shot at a digital series on Marlon Wayan’s digital short website, What the Funny.  We got to talk with Sydney about his season with Funniest Wins,  and what his plans are now that he’s won.

In case you missed it, Funniest Wins was TBS’s summer comedy talent competition.  Hosted by Marlon Wayons, the show started with ten very funny people, and put them through a series of comedy challenges over eight weeks.  The challenges took them through the range of ways to be funny– there was plenty of stand-up but also live sketch, digital shorts, man on the street, hidden camera pranks, vines, creating a bit for animation, and even writing a comedy song and music video.  Sydney Castillo outlasted some very funny people– Christina Pazsitzky, Jason Nash, Manon Mathews, Billy Sorrells, Jenny Zigrino, Tiffany Haddish, Ryan Doom, Key Lewis, and Matt McManus– to win.

funniest wins allThe season finale pitted Castillo against Billy Sorrellis and Jenny Zigrino in a 3 punch challenge- stand up, live sketch, and a digital short, and Sydney came out fighting.  Sydney had been the season favorite.  He won the most challenges, but in the second to last episode, he almost got sent home when show host Marlon Wayans blasted him for a poor performance in the animation challenge.  When we asked Sydney which challenges were most out of his comfort zone, it was an easy answer for him.  “Animation, when I almost got sent home,” he said.  “My stand up is really based on truth, so I was like, I don’t have any truth in animation, so that was my roughest…and Vine.  Cause trying to be funny in six second, I’ve never understood.”   What made it even more difficult was that the animation challenge came at the end, where there were fewer choices to send home if you performed badly.  Castillo remembered what he was thinking when Marlon told him he didn’t like Sydney’s animation.   “Man if i get sent home today I’d be so mad,” Castillo said.  “I was that close to 100,000 and got sent home…?”

The rest of the competitions went much smoother for Sydney.  He won more challenges than any of the other comics, easily.  One of his most memorable moments on the show was his entry in the Original Song episode, which  Castillo calls one of the 5 best sketches he’s ever done.  He teamed up with comedian Christina Pazsitzky to create the hilarious (and catchy) tune, Regular Body.”  “Christina is like a comic’s comic cause she knows how to be funny,” Sydney said, “so working with her was cool cause it was like us, just making jokes. just put a beat behind it.”  Later they had to create a music video to with the song, and the video took Regular Body to another level.  “She was with it just to unveil her stomach.  I was like yo listen, if we’re gonna go here, lets just go here; my mom’s gonna be very disappointed in this footage, but we have to win. And she was like, fill up the bucket, fill up the tub with cheetos lets do this!”

So what’s next for Castillo? Well he’s got $100,000 cash prize, and a deal to create a digital series, which is perfect because he’s looking to get more into development.  The tasks he said, helped him to learn to manage his time, and manage people.  He’s eager to use this momentum to start producing more on a bigger level.

“I would love to do something like Ali G, like how he would mess with people in character. You get to see me being funny and me being in character and messing with people about topical issues and having funny questions. I like messing with people. Any time you see me messing with people I’m having a good time.”

And then there’s the cash.  What’s he going to do with $100k?  “I’m gonna take my mother to Hawaii and then buy me a flat screen tv. Whaaaat? Do something for the family and something for myself? Yeah.”

You can check out Sydney’s comedy out in LA.  This Sunday  and Wednesday he’s performing at the Ha Ha Cafe in North Hollywood and then next Sunday you’ll find him at the West Side Theater in Santa Monica.  And of course visit his website at and on twitter @sydneyisfunny.


Watch Sydney in the “character challenge” where the comics had to go into a speed dating round and annoy their “dates.”

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