Sir Winston Pickles

Surprise returning golden ticket winner brought out from behind the curtain. Tony called him one of his favorite golden ticket winners ever. Performs in white clown face. Age 61. Very dark material; handed out 'caution baby in trunk' bumper stickers.

1. 41:39

   Episode #785

   Sep 14, 2026

   Golden Ticket

   Guests: Duncan Trussell, Kurt Metzger.

   Watch set at 41:39View episode #785
2. 56:10

   Episode #770

   Jun 1, 2026

   Bucket Pull

   Sir Winston Pickles performed in his evil-clown persona. Very dark set - a Boston Marathon bit, a Nancy Guthrie supermarket misdirect, and a toddler-and-shopping-cart joke. Says he writes his jokes at the supermarket, which he visits about four times a week, riffed about his ideal fighting weight being 10 pounds 8 ounces as a 1965 maternity-ward boxing champion and about visiting 'the Alamo' rental-car counter. Golden ticket winner brought back for a rare appearance; originally from England, performs in full custom logo suit. Sheryl told him to change nothing.

   Guests: Tom Segura, Sheryl Underwood.

   Watch set at 56:10View episode #770
3. 1:03:33

   Episode #757

   Feb 23, 2026

   Bucket Pull

   Sir Winston Pickles performed in his evil-clown persona. Returning act given a special non-bucket introduction with a brand new minute, a British evil-clown character from Yorkshire, England, performing in half-and-half clown makeup, tony and the panel singled out his dark sponsor-child punchline as a favorite of the night.

   Guests: Matt Rife, Jeremy (Adam Ray).

   Watch set at 1:03:33View episode #757
4. 31:33

   Episode #750

   Dec 29, 2025

   Bucket Pull

   Sir Winston Pickles performed in his evil-clown persona. Recurring evil-clown character introduced as a special treat with a brand new minute of dark one-liners about a deer, Christmas lights and luminol. In the interview he described spending his days in full makeup running errands, working out at Dick's Sporting Goods, a new rowing machine, and past stints at the DMV and doing DoorDash in character.

   Guests: Lance Armstrong, Matt Mccusker, Tim Butterly.

   Watch set at 31:33View episode #750
5. 1:34:45

   Episode #741

   Oct 27, 2025

   Bucket Pull

   Sir Winston Pickles performed in his evil-clown persona. A character comedian who performs in whiteface and has six years of experience in stand-up. He previously worked as a coal miner and a Premier League photographer in England, tony invited him back as a featured performer due to his unique aesthetic and dark one-liners.

   Guests: Roseanne, Pauly Shore.

   Watch set at 1:34:45View episode #741
6. 5:41

   Episode #732

   Aug 18, 2025

   Bucket Pull

   Sir Winston Pickles performed in his evil-clown persona. A British clown who has been doing stand-up for six years and clowning for ten, he performs a dark set involving his mother's eyes in a jar and a childhood story about keeping a friend's severed fingertip. Tony notes he is not a regular or golden ticket winner but an 'instant legend' invited back for a second time.

   Guests: Ali Siddiq, Kim Congdon.

   Watch set at 5:41View episode #732
7. 49:27

   Episode #728

   Jul 21, 2025

   Bucket Pull

   Sir Winston Pickles performed in his evil-clown persona. A dark-humored clown performer who recently moved to Austin from Florida. He has been a clown for 10 years and doing stand-up for six, and was invited to perform on the Secret Show after his set.

   Guests: Greg Fitzsimmons.

   Watch set at 49:27View episode #728

Career Arc

Sir Winston Pickles is a Kill Tony golden ticket winner. The archive has 7 sets, through #785.

First pulled from the bucket in episode number 728. First set as a golden ticket winner in episode number 785.