Back to comedians

Sir Winston Pickles

First pulled from the bucket in #728. First golden ticket set in #770.

Appearances
7
First episode
#728
Most recent
#785
Current status
Golden Ticket

Career arc

Oldest to newest
first golden ticket
#770

Scroll sideways to see the whole run.

This arc reflects the episodes indexed so far, not the full history of the show.

Appearances

  1. #78541:39Golden TicketSep 7, 2026

    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.

  2. #77056:10Golden TicketMay 18, 2026

    Golden ticket winner brought back for a rare appearance; originally from England, performs in full custom logo suit. 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. Sheryl told him to change nothing.

  3. #7571:03:33FeaturedFeb 16, 2026

    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.

  4. #75031:33FeaturedDec 15, 2025

    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.

  5. #7411:34:45FeaturedOct 13, 2025

    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.

  6. #7325:41FeaturedAug 4, 2025

    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.

  7. #72849:27Bucket PullJul 7, 2025

    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.