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Jonathan Silver


The Scarlet Pirate will be screening on Sunday August 15 at 7:30pm in The Music Box Garden. Production on a new feature comedy film is complete for ‘The Scarlet Pirate’. The film is the second feature from ShowPup Productions and is available now on Vimeo and Amazon. The film shot entirely in Chicago, IL using […]

New Series Trailer – ‘BEAUTIFUL MESS’

ShowPup presents a new series pilot ‘Beautiful Mess’ Sara and Aster, two women struggling in their relationships, find themselves dismantled by the world around them. These friends were brought together by chance and the shared struggle of feeling like their lives haven’t quite started yet. Despite being in their mid 30s, Sara and Aster both […]


Please join us for a screening of Dinner in Hyde Park on Wednesday July 28 as part of the Midwest Film Festival:https://www.midwestfilm.com/get-tickets ShowPup Productions is pleased to present a new short film from Jon Silver. A Chicago writer invites younger versions of himself for dinner, but he is deeply confounded by his ex-girlfriends attendance and […]

“The Civil Hoax: Civil War Deniers” Now Available Online

TRAILER: Trailer – “The Civil Hoax: Civil War Deniers” from ShowPup Network on Vimeo. View The Civil Hoax on Amazon Video

POPPIN’ BOTTLES #20 – Dr. Brown’s Cream Soda with Stephen Kropa

Neo Scum fan Stephen Kropa sneaks onto the ShowPup beach without a badge. He chats about his love of Dr. Brown’s, the origin of the Seven Dwarfs, and Pop Punk. We share our bagel orders and toast with the “Jewish Champagne”. Rob talks whippets and Josh dream of being a housewife. (Please forgive the buzzing!) […]

POPPIN BOTTLES #19 – Fernet Branca with Kellen Terrett

Former Facebook user Dr. Kellen Terrett selects ShowPup to chat about his love of Fernet Branca. He reveals his former roommate, names a segment, and destroys an island. Catch him in It’s Christmas, Goddamnit! soon! Rob let us know why it’s great to never stop learning and heads up our community engagement team. #PopPop Josh […]

POPPIN’ BOTTLES #18 – Brew Dr. Kombucha with Emerald Catron

 Bristleburg‘s own Emerald Catron stops by to chat about growing things in windows, old peaches, and ghost beers. She names her top two Kombucha brands and her top two Alderman candidates: Carlos Rossa (35th Ward) and Rossana Rodriguez (33 Ward). We all agree rent control sucks and Chicago should Lift the Ban on Rent […]

POPPIN’ BOTTLES #17 – Dewar’s White Label with A.J. Miller

Actor and great guy A.J Miller stops by ShowPup to talk about the Kevin James of Scotch, lurking on the scotch Reddit, and his first beer. He surprises the crew with a secret bottle and we learn the importance of batteries. Rob insists on having a bed and Josh celebrates his heritage. **It’s Toddy Time […]


Aliens Space Bats and ShowPup Productions present “Potluck” Written and Starring: Sarah Alò & Ashton Swinford Directed and Edited By: Jon Silver Camera by: Kyle Nilges Sound by: Michael Schiff Featuring: Bella Wholey Puja Mohindra Jose Gonzalez Castro Michael Brackney Janice Summers ShowPup Executive Producers: Jon Silver and Zack Fishman

POPPIN’ BOTTLES – #15 – Macallan 12 Year with Peyton Brown

 Author and comedian Peyton Brown uncorks a couple bottles of Macallan Sherry Oak 12 Year and warns us about drinking overpriced vinegar. He shares his vision for Poppin Bottles last episode and his love of Dorothy Parker. Rob claims he’s a beer guy and Josh loses 100 years. **PALgonquin Round Table** – Rocks Glass […]
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