# ![@sirwinstonpickles Avatar](https://lunarcrush.com/gi/w:26/cr:youtube::UChSmEOBQvUB4gJMOepKVGvQ.png) @sirwinstonpickles Sir Winston Pickles

Sir Winston Pickles posts on YouTube about shorts, sir, dark, austin the most. They currently have [------] followers and [---] posts still getting attention that total [-------] engagements in the last [--] hours.

### Engagements: [-------] [#](/creator/youtube::UChSmEOBQvUB4gJMOepKVGvQ/interactions)
![Engagements Line Chart](https://lunarcrush.com/gi/w:600/cr:youtube::UChSmEOBQvUB4gJMOepKVGvQ/c:line/m:interactions.svg)

- [--] Week [---------] +71%
- [--] Month [---------] +2,234%
- [--] Months [---------] +504%

### Mentions: [--] [#](/creator/youtube::UChSmEOBQvUB4gJMOepKVGvQ/posts_active)
![Mentions Line Chart](https://lunarcrush.com/gi/w:600/cr:youtube::UChSmEOBQvUB4gJMOepKVGvQ/c:line/m:posts_active.svg)

- [--] Week [--] +21%
- [--] Month [--] +70%
- [--] Months [---] +2,140%

### Followers: [------] [#](/creator/youtube::UChSmEOBQvUB4gJMOepKVGvQ/followers)
![Followers Line Chart](https://lunarcrush.com/gi/w:600/cr:youtube::UChSmEOBQvUB4gJMOepKVGvQ/c:line/m:followers.svg)

- [--] Week [------] +3.10%
- [--] Month [------] +9.80%
- [--] Months [------] +71%

### CreatorRank: [------] [#](/creator/youtube::UChSmEOBQvUB4gJMOepKVGvQ/influencer_rank)
![CreatorRank Line Chart](https://lunarcrush.com/gi/w:600/cr:youtube::UChSmEOBQvUB4gJMOepKVGvQ/c:line/m:influencer_rank.svg)

### Social Influence

**Social category influence**
[finance](/list/finance)  [celebrities](/list/celebrities)  [musicians](/list/musicians)  [formula 1](/list/formula-1)  [automotive brands](/list/automotive-brands) 

**Social topic influence**
[shorts](/topic/shorts) #6297, [sir](/topic/sir) #128, [dark](/topic/dark), [austin](/topic/austin), [watch](/topic/watch), [jokes](/topic/jokes), [funny](/topic/funny), [baby](/topic/baby), [clever](/topic/clever), [laughs](/topic/laughs)

**Top accounts mentioned or mentioned by**
[@letstalkcomedyvideos](/creator/undefined) [@sadmanric](/creator/undefined) [@timmynobrakes](/creator/undefined)

**Top assets mentioned**
[YELP INC. (YELP)](/topic/$yelp)
### Top Social Posts
Top posts by engagements in the last [--] hours

"Sir Winston Pickles Dark Humor Comedy Shorts Compilation Enjoy this hilarious compilation of Sir Winston Pickles' darkest and most outrageous jokes Prepare for non-PC humor and quick-fire one-liners that will have you laughing (or gasping). Sir Winston Pickles delivers his signature dark humor with impeccable timing. This compilation features the best bits from recent shorts. If you love dark humor offensive jokes and comedians like Anthony Jeselnik or fans of Kill Tony you're in the right place. Sir Winston Pickles pushes the boundaries of comedy. This video contains adult language and"  
[YouTube Link](https://youtube.com/watch?v=NHwBl2tAYAc)  2026-02-14T05:11Z 20.2K followers, [---] engagements


"The Luminol Laughs: Sir Winston Pickles Unleashed #shorts Join Sir Winston Pickles as he shares his hilarious take on Luminol and its surprising uses From forensic jokes to clever quips this clip is packed with laughter and wit. Don't miss out on the fun#SirWinstonPickles #ComedyGold #ForensicHumor #StandupComedy #KillTony"  
[YouTube Link](https://youtube.com/watch?v=PzUK-7cXlY4)  2026-02-11T16:15Z 20.2K followers, 17.5K engagements


"Sir Winston Pickles Kill Tony 3rd Appearance Episode [---] Official Website https://www.ukjoker.com Follow Me on Instagram: https://www.instagram.com/sirwinstonpickles/ Follow Me on TikTok: https://www.tiktok/sirwinstonpickles/ Follow Me on X: https://www.x.com/WinstonPickles Facebook Official: https://www.facebook.com/picklesflorida Sir Winston Pickles Returns Dark Comedy Clown Set & Interview Kill Tony at the Mothership Sir Winston Pickles makes his long-awaited return to Kill Tony with another razor-sharp dark comedy set delivering brutal one-liners morbid premises and deadpan clown"  
[YouTube Link](https://youtube.com/watch?v=QFIXXlX1-8M)  2025-10-28T16:37Z 20.2K followers, 33.5K engagements


"The Smartest Question Ever Asked on Kill Tony #shorts Watch as Sir Winston Pickles reveals the secret behind his waterproof makeup and the unexpected answer to how he washes it off This hilarious moment showcases the unpredictable nature of Kill Tony. Don't miss out#KillTony #SirWinstonPickles #ComedyMoments #StandupComedy #WaterproofMakeup clown whiteface clown whiteface"  
[YouTube Link](https://youtube.com/watch?v=WZqq8IdEs4E)  2026-01-22T19:46Z 20.2K followers, 2.6M engagements


"Taylor Swift vs Sir Winston Pickles Earworm #shorts Sir Winston Pickles declares war on the Taylor Swift song stuck in his head"  
[YouTube Link](https://youtube.com/watch?v=336zGNRJOxk)  2026-01-27T17:19Z 20.2K followers, 12.2K engagements


"Where's Nancy Strange sounds from the back of a car"  
[YouTube Link](https://youtube.com/watch?v=6VwIj8U0vVE)  2026-02-04T05:55Z 20.2K followers, [----] engagements


"Sir Winston Pickles - Florida Files [----] Sir Winston Pickles Standup Comedy Florida Bits"  
[YouTube Link](https://youtube.com/watch?v=FauAEyE73-4)  2025-06-28T17:01Z 20.1K followers, 14.6K engagements


"Professional Clown Makeup Tutorial Ever wondered how Sir Winston Pickles gets camera-ready In this absurd makeup tutorial parody Sir Winston breaks down his very professional beauty routine while transforming into Taylor Swift Katy Perry and Madonna with rosy cheeks wild eyeshadow thick eyebrows and zero regard for reality. This comedy sketch blends dark humor celebrity impressions and totally questionable beauty advice. From fairytale Taylor Swift vibes to baby Im a firework energy and a brutally simple Madonna look nothing is off limits. 🎭 This is NOT a real makeup tutorial 😂 This IS"  
[YouTube Link](https://youtube.com/watch?v=GiED-57RsMI)  2026-02-02T19:47Z 20.2K followers, [----] engagements


"The Fine Line of Comedy: Whiteface vs Blackface #shorts In this hilarious clip Sir Winston Pickles shares his unique take on the boundaries of comedy and race. With a sharp wit and a nod to Jimmy Kimmel he dives into the controversial topic of whiteface versus blackface. A must-watch for comedy lovers#Comedy #StandUp #SirWinstonPickles #KillTony #RaceInComedy"  
[YouTube Link](https://youtube.com/watch?v=bMSV0s0QKHM)  2026-02-02T15:40Z 20.2K followers, 37.5K engagements


"The Mexican Lady Eyebrows of Sir Winston Pickles #shorts Check out this hilarious moment from Sir Winston Pickles' appearance on Kill Tony His red eyes and unique eyebrows are the talk of the town. What do you think#SirWinstonPickles #ComedyClip #VapingEffects #StandupComedy #FunnyMoments"  
[YouTube Link](https://youtube.com/watch?v=g9yEv4Y_BOE)  2026-02-09T05:33Z 20.2K followers, 19K engagements


"Kids Toddlers & Babies Are Overrated Dark Comedy Rant Kids. Toddlers. Babies. No this is not one of those arent they magical videos. In this dark stand-up comedy set Sir Winston Pickles delivers a brutally honest (and wildly inappropriate) rant about kids in restaurants toddlers in stores babies on vacation Amber Alerts baby photos on phones and why childfree adults might be onto something. From overdramatic kids and stolen bicycles to babies in restaurants supermarket meltdowns and nostalgic memories of the good old days this set leans hard into dark humor sarcasm and observational comedy"  
[YouTube Link](https://youtube.com/watch?v=lB6KHQJr1Zg)  2026-02-07T01:37Z 20.2K followers, [---] engagements


"Kill Tonys Sir Winston Pickles: Dark Humor Clown Comedy & Stand-Up Secrets Full Interview Official Website https://www.ukjoker.com Follow Me on X: https://x.com/WinstonPickles Facebook Official: https://www.facebook.com/picklesflorida Follow Me on Instagram: https://www.instagram.com/sirwinstonpickles/ Follow Me on TikTok: https://www.tiktok.com/@sirwinstonpickles Sir Winston Pickles Full Kill Tony Set + Interview Dark Clown Comedy That Earned a Second Minute Sir Winston Pickles delivers one of the most unforgettable performances in Kill Tony history combining razor-sharp dark humor with a"  
[YouTube Link](https://youtube.com/watch?v=q71Xu-IZbcM)  2025-07-22T18:47Z 19.4K followers, 661.8K engagements


"Machine Gun DeGeneres"  
[YouTube Link](https://youtube.com/watch?v=-9Gxw02wj1I)  2025-09-24T04:42Z 16K followers, [----] engagements


"Surgery on a Budget"  
[YouTube Link](https://youtube.com/watch?v=-emDHxAhm3M)  2025-09-13T05:52Z 15.5K followers, [----] engagements


"Timmy No Brakes Sir Winston Pickles Clown Talk Check out Timmy No Brakes at https://www.instagram.com/timmynobrakes/ Full Podcast can be found at https://www.youtube.com/watchv=H1PWsos_Yq4 Official Website https://www.sirpickles.com Follow Me on Twitter: https://twitter.com/WinstonPickles Facebook Official: https://www.facebook.com/picklesflorida Facebook Group: https://www.facebook.com/groups/503765280226912 Follow Me on Instagram: https://www.instagram.com/sirwinstonpickles/"  
[YouTube Link](https://youtube.com/watch?v=10UYHmbpE4s)  2025-07-31T18:52Z 16.2K followers, 18.8K engagements


"Love Thy Neighbour"  
[YouTube Link](https://youtube.com/watch?v=1Gtb-Pn7YLk)  2025-09-19T14:51Z 15.8K followers, [----] engagements


"Work Promotion Ladder"  
[YouTube Link](https://youtube.com/watch?v=1SrcY9UVLpY)  2025-10-09T05:47Z 16.4K followers, 22.7K engagements


"Miner Minors"  
[YouTube Link](https://youtube.com/watch?v=2Px4FitrhQU)  2025-09-30T13:59Z 16.2K followers, 15.4K engagements


"Baby Photos"  
[YouTube Link](https://youtube.com/watch?v=4S7NbL4tZ98)  2025-08-29T05:16Z 14.5K followers, 17.7K engagements


"Precious Cargo"  
[YouTube Link](https://youtube.com/watch?v=4mdu29PxcS0)  2025-10-13T04:55Z 16.6K followers, [----] engagements


"Bank Tellers"  
[YouTube Link](https://youtube.com/watch?v=5A8oGHHzlH0)  2025-09-02T17:35Z 15K followers, 17.6K engagements


"Tribal Tattoo"  
[YouTube Link](https://youtube.com/watch?v=5IzhEqqjg2I)  2025-09-07T14:37Z 15.2K followers, [----] engagements


"Owls Know Who"  
[YouTube Link](https://youtube.com/watch?v=6ZU0GwEzEnw)  2025-08-24T13:30Z 13.7K followers, 20.6K engagements


"Babies Falling From Trees"  
[YouTube Link](https://youtube.com/watch?v=9hb-JqDxKX8)  2025-09-25T05:33Z 16K followers, [----] engagements


"Total Confusion"  
[YouTube Link](https://youtube.com/watch?v=AGB3Vle36K4)  2025-10-14T14:49Z 16.6K followers, [----] engagements


"School Zone Limits"  
[YouTube Link](https://youtube.com/watch?v=CGk4sMi3vXY)  2025-09-22T06:22Z 15.9K followers, [----] engagements


"Fairground Food"  
[YouTube Link](https://youtube.com/watch?v=Ccw7ch6QB20)  2025-10-10T05:18Z 16.5K followers, [----] engagements


"Bicycle Theft"  
[YouTube Link](https://youtube.com/watch?v=Cfwt8Z_CNbA)  2025-09-23T07:43Z 16K followers, [----] engagements


"Dogs and Toddlers"  
[YouTube Link](https://youtube.com/watch?v=I-B7kup0qzo)  2025-08-28T05:58Z 14.2K followers, 15.7K engagements


"Amber Alerts"  
[YouTube Link](https://youtube.com/watch?v=KtO_Xj-Hmjw)  2025-10-08T05:26Z 16.4K followers, [----] engagements


"Office Staples"  
[YouTube Link](https://youtube.com/watch?v=L0wvkWFyPW8)  2025-09-20T06:50Z 15.8K followers, [----] engagements


"Cry at Weddings"  
[YouTube Link](https://youtube.com/watch?v=L12UEc-MZ_E)  2025-08-26T21:55Z 14.5K followers, 23.8K engagements


"Burning Bridges"  
[YouTube Link](https://youtube.com/watch?v=LffVYJIB61g)  2025-10-15T04:47Z 16.7K followers, [----] engagements


"Dyslexia Blowback"  
[YouTube Link](https://youtube.com/watch?v=PdFxb3xQmLA)  2025-08-22T14:54Z 15.2K followers, 116.7K engagements


"Born With a Silver Spoon"  
[YouTube Link](https://youtube.com/watch?v=PmA_qGB_r7w)  2025-08-25T09:52Z 13.7K followers, 17.4K engagements


"Perfect Kill Tony Minute Let's Talk Comedy Critique Critique of my very first appearance on Kill Tony by Legendary Comedian Gary Michaels. Check out more of Gary's Comedy Content at: https://www.youtube.com/@LetsTalkComedy/videos Official Website https://www.sirpickles.com Follow Me on Twitter: https://twitter.com/WinstonPickles Facebook Official: https://www.facebook.com/picklesflorida Facebook Group: https://www.facebook.com/groups/503765280226912 Follow Me on Instagram: https://www.instagram.com/sirwinstonpickles/"  
[YouTube Link](https://youtube.com/watch?v=Rn28I62UdrQ)  2025-10-08T16:09Z 16.4K followers, [---] engagements


"Global Shortening"  
[YouTube Link](https://youtube.com/watch?v=Y5IQKve03-c)  2025-09-21T05:56Z 15.9K followers, [----] engagements


"Earning Their Keep"  
[YouTube Link](https://youtube.com/watch?v=Zz6R4kswIb4)  2025-10-04T04:26Z 16.2K followers, [----] engagements


"Shopping Safety"  
[YouTube Link](https://youtube.com/watch?v=gYhGFVzajuM)  2025-10-07T04:47Z 16.3K followers, [----] engagements


"Red Grandmother"  
[YouTube Link](https://youtube.com/watch?v=gjw9YkeeQBY)  2025-09-08T06:39Z 15.2K followers, [----] engagements


"Trick or Treat"  
[YouTube Link](https://youtube.com/watch?v=h38uqC4zdTc)  2025-10-11T03:57Z 16.5K followers, 13.2K engagements


"Adolf Ruins Everything"  
[YouTube Link](https://youtube.com/watch?v=miZzMeCkbm0)  2025-08-26T06:58Z 14.2K followers, 16.8K engagements


"Egg Shopping"  
[YouTube Link](https://youtube.com/watch?v=neCj6-3FpU8)  2025-09-01T05:23Z 14.8K followers, 11.4K engagements


"Funnybone Orlando Florida"  
[YouTube Link](https://youtube.com/watch?v=ngIxe58-n5Q)  2025-08-23T19:00Z 14.5K followers, 31.5K engagements


"House Exorcism"  
[YouTube Link](https://youtube.com/watch?v=tZ2C1mPtaXE)  2025-09-14T05:32Z 15.6K followers, [----] engagements


"Guantanamo Bay Yelp Reviews"  
[YouTube Link](https://youtube.com/watch?v=ta51v_eNoCM)  2025-08-22T04:58Z 14.8K followers, 22.6K engagements


"Third Responder"  
[YouTube Link](https://youtube.com/watch?v=x1z5tVC_vSM)  2025-09-12T05:52Z 15.5K followers, [----] engagements


"Sir Winston Pickles Kill Tony Appearance [--] Ep #750 Official Website https://www.ukjoker.com Follow Me on Instagram: https://www.instagram.com/sirwinstonpickles/ Follow Me on TikTok: https://www.tiktok/sirwinstonpickles/ Follow Me on X: https://www.x.com/WinstonPickles Facebook Official: https://www.facebook.com/picklesflorida Sir Winston Pickles Dark Comedy Clown Set Kill Tony Appearance Clown Products I use are listed at the bottom of this description Sir Winston Pickles returns with a brand-new dark comedy minute delivering twisted one-liners deadpan misdirection and sinister clown humor"  
[YouTube Link](https://youtube.com/watch?v=444XYfvp6ww)  2025-12-30T05:35Z 20.2K followers, 18.8K engagements


"Blame The Other Guy"  
[YouTube Link](https://youtube.com/watch?v=4xtWjnQJfpE)  2025-11-04T07:14Z 17.4K followers, 11K engagements


"Santa Tantrum"  
[YouTube Link](https://youtube.com/watch?v=6DTc6nlfk4o)  2025-10-27T05:54Z 17K followers, [----] engagements


"Ric Diez Talks with Sir Winston Pickles - Darkness Collides Find more Ric Diez content @ https://www.youtube.com/@SadManRic and https://www.instagram.com/sadmanric/ Official Website https://www.ukjoker.com Follow Me on Instagram: https://www.instagram.com/sirwinstonpickles/ Follow Me on TikTok: https://www.tiktok/sirwinstonpickles/ Follow Me on X: https://www.x.com/WinstonPickles Facebook Official: https://www.facebook.com/picklesflorida"  
[YouTube Link](https://youtube.com/watch?v=Ih9Uj6SSxyY)  2025-11-04T21:19Z 17.4K followers, [----] engagements


"Cruise Ship Comedy: Overboard Humor #shorts Join Sir Winston Pickles as he hilariously discusses the dark side of cruise ships and the absurdity of disappearing passengers. A must-watch for comedy lovers#CruiseComedy #SirWinstonPickles #StandupHumor #KillTony #Comedy"  
[YouTube Link](https://youtube.com/watch?v=KAg2oDQzZ1Y)  2026-01-13T18:24Z 20.2K followers, 12.6K engagements


"Halloween Clown"  
[YouTube Link](https://youtube.com/watch?v=KTjsFvU3gxE)  2025-10-22T06:00Z 16.8K followers, [----] engagements


"Opportunities"  
[YouTube Link](https://youtube.com/watch?v=KenH9qobfwQ)  2026-01-02T02:57Z 20.2K followers, [----] engagements


"Health Insurance Tips"  
[YouTube Link](https://youtube.com/watch?v=L99Ay5TzqEI)  2025-11-19T05:06Z 17.7K followers, [----] engagements


"Space Discrepancy A hilarious stand-up comedy clip featuring a sharp observational joke about conspiracy theories and Star Trek. With dry humor and clever misdirection Winston Pickles riffs on skepticism pop culture and the shocking realization that Star Trek might not be a documentary after all. Perfect for fans of smart comedy nerd humor sci-fi jokes and stand-up clips that blend absurd logic with deadpan delivery. Ideal for audiences who love comedy about conspiracies television and cultural overthinking"  
[YouTube Link](https://youtube.com/watch?v=LtZYhRQSihM)  2026-01-11T05:36Z 20.2K followers, [----] engagements


"Olive Garden B.S"  
[YouTube Link](https://youtube.com/watch?v=QtGTsMYSsGI)  2025-12-21T06:28Z 20.2K followers, [----] engagements


"Remembering the Most Beautiful Loss #shorts In this clip we reflect on the tragic loss of a stunning Mercedes Benz that has been gone for almost [--] years. Join us as we dive into nostalgia and beauty in the automotive world.#MercedesBenz #CarNostalgia #AutomotiveBeauty #ClassicCars #CarEnthusiast"  
[YouTube Link](https://youtube.com/watch?v=RAs8bb4v9xk)  2026-01-19T05:03Z 20.2K followers, 15.6K engagements


"Roadside Hazards"  
[YouTube Link](https://youtube.com/watch?v=Uc2Hc8EF2kA)  2025-11-05T04:57Z 17.5K followers, 12.7K engagements


"Baby Smoothie"  
[YouTube Link](https://youtube.com/watch?v=dOQF7wP4czM)  2025-11-02T06:06Z 17.3K followers, [----] engagements


"School Zones"  
[YouTube Link](https://youtube.com/watch?v=e2Pz0RVch2Q)  2025-10-28T08:23Z 16.9K followers, [----] engagements


"Sir Winston Pickles: The Jogging Safety Patrol #shorts Join Sir Winston Pickles as he shares his hilarious take on staying fit and keeping the neighborhood safe This clip is packed with dark humor and a unique perspective on jogging. Don't miss out on the laughs#SirWinstonPickles #DarkHumor #StandUpComedy #ComedyClip #JoggingSafety Active Lifestyle Canine Care Dog Adventures Dog Jogging Dog Training Fitness Patrol Funny Dogs Jogging Humor Jogging Safety Lighthearted Shorts Pet Comedy Pet Safety Running Tips Safety Awareness Safety Patrol Shorts Video Sir Winston Pickles Urban Jogging Winston"  
[YouTube Link](https://youtube.com/watch?v=eXbqd8ozvtU)  2026-01-16T05:20Z 20.2K followers, 25.2K engagements


"Sir Winston Pickles Kill Tony Appearance Episode [---] Official Website https://www.ukjoker.com Facebook Official: https://www.facebook.com/picklesflorida Facebook Group: https://www.facebook.com/groups/503765280226912 Follow Me on Instagram: https://www.instagram.com/sirwinstonpickles/"  
[YouTube Link](https://youtube.com/watch?v=f4N9e90FTqk)  2025-08-19T05:46Z 17.9K followers, 79.2K engagements


"# #viralvideo #shortvideo #beard"  
[YouTube Link](https://youtube.com/watch?v=fXZAa8D290A)  2025-11-21T17:48Z 111K followers, 22.8K engagements


"Sir Winston Pickles First [--] Kill Tony Appearances [----] Official Website https://www.ukjoker.com Follow Me on Instagram: https://www.instagram.com/sirwinstonpickles/ Follow Me on TikTok: https://www.tiktok/sirwinstonpickles/ Follow Me on X: https://www.x.com/WinstonPickles Facebook Official: https://www.facebook.com/picklesflorida"  
[YouTube Link](https://youtube.com/watch?v=hbjJwmLp5TY)  2025-10-30T05:19Z 17K followers, [---] engagements


"Better Gas Mileage"  
[YouTube Link](https://youtube.com/watch?v=ighgJ6m3KuI)  2025-10-18T05:15Z 16.8K followers, [----] engagements


"Speed Bumps"  
[YouTube Link](https://youtube.com/watch?v=ljuLXpSP_VE)  2025-12-31T18:34Z 20.2K followers, [----] engagements


"In Your Head"  
[YouTube Link](https://youtube.com/watch?v=mkKAUHNy6Ac)  2025-11-07T06:03Z 17.5K followers, 23.4K engagements


"Homeschooling"  
[YouTube Link](https://youtube.com/watch?v=mzLn1l7rrP0)  2025-11-09T06:53Z 17.6K followers, [----] engagements


"Cruise Ship Babies"  
[YouTube Link](https://youtube.com/watch?v=nCpyGlx8igg)  2025-11-06T06:42Z 17.5K followers, [----] engagements


"Ed Geins Collection"  
[YouTube Link](https://youtube.com/watch?v=nEa6ahQ40kU)  2025-10-19T05:06Z 16.8K followers, [----] engagements


"2026 Fireworks 🎇"  
[YouTube Link](https://youtube.com/watch?v=nWVS4029xSQ)  2026-01-01T09:56Z 20.2K followers, [----] engagements


"Hide and Seek"  
[YouTube Link](https://youtube.com/watch?v=noPIwNLmyrk)  2025-10-29T06:53Z 17.1K followers, [----] engagements


"The Human Cannonball: A Darkly Funny Tribute #shorts A hilarious yet dark moment from our interview with Sir Winston Pickles where we remember the human cannonball and his unforgettable spirit. Join us for a laugh and a touch of absurdity#DarkHumor #ComedyClip #StandUpComedy #SirWinstonPickles #HumanCannonball"  
[YouTube Link](https://youtube.com/watch?v=rbkEE93AA7Q)  2026-01-15T04:55Z 20.2K followers, 15.1K engagements


"Get Me Out of Here"  
[YouTube Link](https://youtube.com/watch?v=sfEHZ3CIA0o)  2025-11-14T06:21Z 17.6K followers, 10.9K engagements


"Panda Sandwich"  
[YouTube Link](https://youtube.com/watch?v=tgRH528I0bE)  2025-11-21T05:39Z 17.7K followers, [----] engagements


"Firehouse Baby"  
[YouTube Link](https://youtube.com/watch?v=vzL4L14HBvY)  2025-12-09T06:20Z 20.2K followers, [----] engagements


"Term Limits"  
[YouTube Link](https://youtube.com/watch?v=y7QrA8pl2QA)  2025-11-13T12:39Z 17.6K followers, [----] engagements


"ASMR Origins"  
[YouTube Link](https://youtube.com/watch?v=yZHnP7lu4OU)  2025-10-16T04:41Z 16.7K followers, 13.1K engagements


"Speeding Through School Zones: A Comedic Take #shorts Join Sir Winston Pickles as he hilariously critiques the absurdity of [--] mph school zones. Is it really worth the risk This clip from his latest appearance on Kill Tony will have you laughing out loud#SirWinstonPickles #ComedyClip #StandupComedy #KillTony #FunnyMoments"  
[YouTube Link](https://youtube.com/watch?v=zWm3bT09x00)  2026-01-18T17:52Z 20.2K followers, 29.3K engagements


"The Truth About Pronouns: Group Discounts #shorts In this clip we dive into a humorous take on the use of they/them pronouns and the misconceptions surrounding them. Are people really just trying to save on health insurance Watch to find out#Pronouns #TheyThem #Humor #Misconceptions #HealthInsurance"  
[YouTube Link](https://youtube.com/watch?v=EBMFYzp_Ces)  2026-02-15T05:51Z 20.2K followers, [----] engagements


"The Hilarious High Chair Taping Incident #shorts Join me as I share the story of my unforgettable taping session at Olive Garden where I hilariously taped a toddler to his high chair and received a round of applause You won't want to miss this funny moment#FunnyMoments #ParentingFails #OliveGarden #ComedyClip #ViralVideo"  
[YouTube Link](https://youtube.com/watch?v=GDpdPhkj0yo)  2026-02-14T15:41Z 20.2K followers, [----] engagements


"Sir Winston Pickles Dark Humor Comedy Shorts Compilation Enjoy this hilarious compilation of Sir Winston Pickles' darkest and most outrageous jokes Prepare for non-PC humor and quick-fire one-liners that will have you laughing (or gasping). Sir Winston Pickles delivers his signature dark humor with impeccable timing. This compilation features the best bits from recent shorts. If you love dark humor offensive jokes and comedians like Anthony Jeselnik or fans of Kill Tony you're in the right place. Sir Winston Pickles pushes the boundaries of comedy. This video contains adult language and"  
[YouTube Link](https://youtube.com/watch?v=NHwBl2tAYAc)  2026-02-14T05:11Z 20.2K followers, [---] engagements


"Monster Under the Bed #shorts Ever had a kid shout about monsters Uncle Winston has a unique way of handling it 😂 #DarkComedy #Standup#SirWinstonPickles #DarkComedy #StandupComedy #FloridaComedy #KidsAreOverrated"  
[YouTube Link](https://youtube.com/watch?v=BjMvzJlAZPs)  2026-02-12T04:51Z 20.2K followers, [----] engagements


"The Luminol Laughs: Sir Winston Pickles Unleashed #shorts Join Sir Winston Pickles as he shares his hilarious take on Luminol and its surprising uses From forensic jokes to clever quips this clip is packed with laughter and wit. Don't miss out on the fun#SirWinstonPickles #ComedyGold #ForensicHumor #StandupComedy #KillTony"  
[YouTube Link](https://youtube.com/watch?v=PzUK-7cXlY4)  2026-02-11T16:15Z 20.2K followers, 17.5K engagements


"Ready For 2026"  
[YouTube Link](https://youtube.com/watch?v=ly5R3rENuGU)  2026-02-11T06:33Z 20.2K followers, [----] engagements


"Taylor Swift Makeup Tutorial Clown Edition #shorts Ever wondered how to channel your inner Taylor Swift while doing clown makeup This clip reveals the secret to nailing that iconic look with a twist Get ready for some laughs and unexpected tips#TaylorSwift #ClownMakeup #Comedy #MakeupTutorial #FunnyMoments"  
[YouTube Link](https://youtube.com/watch?v=w8EW8_vnaeY)  2026-02-11T05:18Z 20.2K followers, [----] engagements


"The Heartbreaking Truth About Sponsorship #shorts Discover the emotional journey of sponsoring a child and the unexpected consequences of a simple oversight. This clip reveals how a small mistake can lead to heartbreaking news. Don't miss this touching moment#Sponsorship #ChildAid #EmotionalStory #Heartbreak #NonProfit"  
[YouTube Link](https://youtube.com/watch?v=ohKlLTHz23M)  2026-02-09T19:36Z 20.2K followers, [----] engagements


"The Mexican Lady Eyebrows of Sir Winston Pickles #shorts Check out this hilarious moment from Sir Winston Pickles' appearance on Kill Tony His red eyes and unique eyebrows are the talk of the town. What do you think#SirWinstonPickles #ComedyClip #VapingEffects #StandupComedy #FunnyMoments"  
[YouTube Link](https://youtube.com/watch?v=g9yEv4Y_BOE)  2026-02-09T05:33Z 20.2K followers, 19K engagements


"The Overdramatic Kids and Their Bikes #shorts Ever seen a kid's face when their bike gets stolen It's pure drama Join me as I share my thoughts on how kids today are just a bit too over the top. #Comedy #Kids #Overdramatic#OverdramaticKids #ComedyRant #StandupComedy #DarkHumor #BicycleDrama"  
[YouTube Link](https://youtube.com/watch?v=wKrE4UYlGKI)  2026-02-08T06:33Z 20.2K followers, 21.5K engagements


"A Hilarious Tip for Cruise Ship Patrons #shorts Ever wondered how to deal with annoying kids on a cruise Here's a cheeky tip that might just make you chuckle Dive into this dark comedy rant and discover the lighter side of parenting on the high seas. #Comedy #CruiseLife#DarkComedy #CruiseTips #ParentingHumor #StandupComedy #FunnyMoments"  
[YouTube Link](https://youtube.com/watch?v=6A36FPBVOCM)  2026-02-07T15:06Z 20.2K followers, [----] engagements


"Kids Toddlers & Babies Are Overrated Dark Comedy Rant Kids. Toddlers. Babies. No this is not one of those arent they magical videos. In this dark stand-up comedy set Sir Winston Pickles delivers a brutally honest (and wildly inappropriate) rant about kids in restaurants toddlers in stores babies on vacation Amber Alerts baby photos on phones and why childfree adults might be onto something. From overdramatic kids and stolen bicycles to babies in restaurants supermarket meltdowns and nostalgic memories of the good old days this set leans hard into dark humor sarcasm and observational comedy"  
[YouTube Link](https://youtube.com/watch?v=lB6KHQJr1Zg)  2026-02-07T01:37Z 20.2K followers, [---] engagements


"Kwame's Shrunken Head: A Twist of Fate #shorts In this hilarious update we reveal how little Kwame's family turned a quirky situation into a financial win You won't believe what they sold to a tourist 😂 #Kwame #ShrunkenHead #FunnyStory#Kwame #ShrunkenHead #FunnyStory #ViralVideo #Comedy"  
[YouTube Link](https://youtube.com/watch?v=UXGK6W7cmPw)  2026-02-06T05:54Z 20.2K followers, [----] engagements


"The One Time My Mom Hit Me #shorts In this hilarious clip I share the unforgettable moment when my mom accidentally hit me while reversing the car. It's a story of love laughter and a little bit of chaos#FunnyMoments #FamilyStories #CarAccident #ComedyClip #Relatable"  
[YouTube Link](https://youtube.com/watch?v=KP2rMXPIA0s)  2026-02-05T16:21Z 20.2K followers, [----] engagements


"Where's Nancy Strange sounds from the back of a car"  
[YouTube Link](https://youtube.com/watch?v=6VwIj8U0vVE)  2026-02-04T05:55Z 20.2K followers, [----] engagements


"The Real Horror of True Crime Shows #shorts Ever wondered what truly haunts you in true crime documentaries It's not the crime itself but those old photographs they dig up Join us as we explore the unsettling side of true crime TV.#TrueCrime #Documentary #CreepyPhotos #Horror #TVShows"  
[YouTube Link](https://youtube.com/watch?v=w4iXnSdKw_M)  2026-02-03T06:12Z 20.2K followers, [----] engagements


"Professional Clown Makeup Tutorial Ever wondered how Sir Winston Pickles gets camera-ready In this absurd makeup tutorial parody Sir Winston breaks down his very professional beauty routine while transforming into Taylor Swift Katy Perry and Madonna with rosy cheeks wild eyeshadow thick eyebrows and zero regard for reality. This comedy sketch blends dark humor celebrity impressions and totally questionable beauty advice. From fairytale Taylor Swift vibes to baby Im a firework energy and a brutally simple Madonna look nothing is off limits. 🎭 This is NOT a real makeup tutorial 😂 This IS"  
[YouTube Link](https://youtube.com/watch?v=GiED-57RsMI)  2026-02-02T19:47Z 20.2K followers, [----] engagements


"Make Today Unforgettable #shorts Discover how a simple act can turn an ordinary day into an unforgettable experience for someone you don't even know. Let's spread joy and laughter#UnforgettableMoments #SpreadJoy #RandomActsOfKindness #MakeSomeoneSmile #LifeIsBeautiful"  
[YouTube Link](https://youtube.com/watch?v=3eboOR5WzQI)  2026-02-02T17:06Z 20.2K followers, [----] engagements


"The Fine Line of Comedy: Whiteface vs Blackface #shorts In this hilarious clip Sir Winston Pickles shares his unique take on the boundaries of comedy and race. With a sharp wit and a nod to Jimmy Kimmel he dives into the controversial topic of whiteface versus blackface. A must-watch for comedy lovers#Comedy #StandUp #SirWinstonPickles #KillTony #RaceInComedy"  
[YouTube Link](https://youtube.com/watch?v=bMSV0s0QKHM)  2026-02-02T15:40Z 20.2K followers, 37.5K engagements


"You Can't Say What on Television #shorts"  
[YouTube Link](https://youtube.com/watch?v=u0Q_p5DCYI8)  2026-01-31T05:53Z 20.2K followers, [----] engagements


"Homeless bed outrage #shorts A bold message to realtors: advertising homes on the beds of the homeless is not just unethical it's a serious issue. Let's talk about respect and responsibility in real estate#RealEstate #Ethics #Homelessness #Realtors #Respect"  
[YouTube Link](https://youtube.com/watch?v=1Jyl2Ec_nag)  2026-01-30T14:32Z 20.2K followers, [----] engagements


"I Can Locate All My Bowel Movements Now #shorts Sir Winston Pickles uses GPS AirTags to track and locate his own bowel movements because science has gone too far and no one stopped him in time. This is dark comedy absurd logic and unnecessary technology colliding in under [--] seconds. True crime energy. Zero crimes. Maximum regret. Follow for more Sir Winston Pickles comedy shorts unhinged experiments and ideas that absolutely didnt need GPS"  
[YouTube Link](https://youtube.com/watch?v=ffQHq9FTljk)  2026-01-29T05:55Z 20.2K followers, 15.2K engagements


"Taylor Swift vs Sir Winston Pickles Earworm #shorts Sir Winston Pickles declares war on the Taylor Swift song stuck in his head"  
[YouTube Link](https://youtube.com/watch?v=336zGNRJOxk)  2026-01-27T17:19Z 20.2K followers, 12.2K engagements


"Be Careful With Credit Card Expiration Dates Sir Winston highlights the perils of not keeping up with minor banking details"  
[YouTube Link](https://youtube.com/watch?v=my6vijZ9WU4)  2026-01-25T06:03Z 20.2K followers, 11.3K engagements


"The Smartest Question Ever Asked on Kill Tony #shorts Watch as Sir Winston Pickles reveals the secret behind his waterproof makeup and the unexpected answer to how he washes it off This hilarious moment showcases the unpredictable nature of Kill Tony. Don't miss out#KillTony #SirWinstonPickles #ComedyMoments #StandupComedy #WaterproofMakeup clown whiteface clown whiteface"  
[YouTube Link](https://youtube.com/watch?v=WZqq8IdEs4E)  2026-01-22T19:46Z 20.2K followers, 2.6M engagements


"This Question Breaks Every Gas Station Employee #shorts Asking a gas station employee where the nearest gas station is will never stop being funny 😂 Quick stand-up comedy short from Sir Winston Pickles featuring dry humor awkward moments and classic observational comedy. If you love absurd questions deadpan delivery and short stand-up clips this one hits fast. #Shorts #ComedyShorts #StandUpComedy #Funny #ObservationalComedy #DryHumor #Awkward #SirWinstonPickles #ViralShorts #Comedy crazy customers customer encounters employee confessions employee stories funny questions gas station banter"  
[YouTube Link](https://youtube.com/watch?v=A6KVGRgQaB8)  2026-01-22T06:33Z 20.2K followers, [----] engagements


"Remembering the Most Beautiful Loss #shorts In this clip we reflect on the tragic loss of a stunning Mercedes Benz that has been gone for almost [--] years. Join us as we dive into nostalgia and beauty in the automotive world.#MercedesBenz #CarNostalgia #AutomotiveBeauty #ClassicCars #CarEnthusiast"  
[YouTube Link](https://youtube.com/watch?v=RAs8bb4v9xk)  2026-01-19T05:03Z 20.2K followers, 15.6K engagements


"Speeding Through School Zones: A Comedic Take #shorts Join Sir Winston Pickles as he hilariously critiques the absurdity of [--] mph school zones. Is it really worth the risk This clip from his latest appearance on Kill Tony will have you laughing out loud#SirWinstonPickles #ComedyClip #StandupComedy #KillTony #FunnyMoments"  
[YouTube Link](https://youtube.com/watch?v=zWm3bT09x00)  2026-01-18T17:52Z 20.2K followers, 29.3K engagements


"Sir Winston Pickles: The Jogging Safety Patrol #shorts Join Sir Winston Pickles as he shares his hilarious take on staying fit and keeping the neighborhood safe This clip is packed with dark humor and a unique perspective on jogging. Don't miss out on the laughs#SirWinstonPickles #DarkHumor #StandUpComedy #ComedyClip #JoggingSafety Active Lifestyle Canine Care Dog Adventures Dog Jogging Dog Training Fitness Patrol Funny Dogs Jogging Humor Jogging Safety Lighthearted Shorts Pet Comedy Pet Safety Running Tips Safety Awareness Safety Patrol Shorts Video Sir Winston Pickles Urban Jogging Winston"  
[YouTube Link](https://youtube.com/watch?v=eXbqd8ozvtU)  2026-01-16T05:20Z 20.2K followers, 25.2K engagements


"The Human Cannonball: A Darkly Funny Tribute #shorts A hilarious yet dark moment from our interview with Sir Winston Pickles where we remember the human cannonball and his unforgettable spirit. Join us for a laugh and a touch of absurdity#DarkHumor #ComedyClip #StandUpComedy #SirWinstonPickles #HumanCannonball"  
[YouTube Link](https://youtube.com/watch?v=rbkEE93AA7Q)  2026-01-15T04:55Z 20.2K followers, 15.1K engagements


"Disqualified for Sneakers 😂 #shorts Watch as Sir Winston Pickles shares his hilarious experience of getting disqualified from a drag race for wearing sneakers instead of high heels This clip is a must-see for comedy lovers#SirWinstonPickles #DragRaceFail #ComedyClip #StandupComedy #KillTony"  
[YouTube Link](https://youtube.com/watch?v=fBlrOI5Cq-k)  2026-01-14T04:56Z 20.2K followers, 16.1K engagements


"Cruise Ship Comedy: Overboard Humor #shorts Join Sir Winston Pickles as he hilariously discusses the dark side of cruise ships and the absurdity of disappearing passengers. A must-watch for comedy lovers#CruiseComedy #SirWinstonPickles #StandupHumor #KillTony #Comedy"  
[YouTube Link](https://youtube.com/watch?v=KAg2oDQzZ1Y)  2026-01-13T18:24Z 20.2K followers, 12.6K engagements


"Flooding the Living Room with a Rowing Machine #shorts Join Sir Winston Pickles as he hilariously shares his experience of working out at Dick's Sporting Goods and the unexpected consequences of his new rowing machine. You won't believe what happens next#SirWinstonPickles #StandupComedy #ComedyClip #RowingMachine #FunnyMoments"  
[YouTube Link](https://youtube.com/watch?v=07VCLK5REm8)  2026-01-13T05:49Z 20.2K followers, 33K engagements


"Space Discrepancy A hilarious stand-up comedy clip featuring a sharp observational joke about conspiracy theories and Star Trek. With dry humor and clever misdirection Winston Pickles riffs on skepticism pop culture and the shocking realization that Star Trek might not be a documentary after all. Perfect for fans of smart comedy nerd humor sci-fi jokes and stand-up clips that blend absurd logic with deadpan delivery. Ideal for audiences who love comedy about conspiracies television and cultural overthinking"  
[YouTube Link](https://youtube.com/watch?v=LtZYhRQSihM)  2026-01-11T05:36Z 20.2K followers, [----] engagements


"M.B. Head Games"  
[YouTube Link](https://youtube.com/watch?v=NlQKEknocm0)  2026-01-10T06:09Z 20.2K followers, [----] engagements


"Background Checks"  
[YouTube Link](https://youtube.com/watch?v=mJ2KiPWu0VA)  2026-01-07T07:30Z 20.2K followers, [----] engagements


"Opportunities"  
[YouTube Link](https://youtube.com/watch?v=KenH9qobfwQ)  2026-01-02T02:57Z 20.2K followers, [----] engagements


"2026 Fireworks 🎇"  
[YouTube Link](https://youtube.com/watch?v=nWVS4029xSQ)  2026-01-01T09:56Z 20.2K followers, [----] engagements


"Speed Bumps"  
[YouTube Link](https://youtube.com/watch?v=ljuLXpSP_VE)  2025-12-31T18:34Z 20.2K followers, [----] engagements


"Happy New Year 🙏"  
[YouTube Link](https://youtube.com/watch?v=03M6BsCPLMs)  2025-12-30T18:39Z 20.2K followers, [----] engagements


"Sir Winston Pickles Kill Tony Appearance [--] Ep #750 Official Website https://www.ukjoker.com Follow Me on Instagram: https://www.instagram.com/sirwinstonpickles/ Follow Me on TikTok: https://www.tiktok/sirwinstonpickles/ Follow Me on X: https://www.x.com/WinstonPickles Facebook Official: https://www.facebook.com/picklesflorida Sir Winston Pickles Dark Comedy Clown Set Kill Tony Appearance Clown Products I use are listed at the bottom of this description Sir Winston Pickles returns with a brand-new dark comedy minute delivering twisted one-liners deadpan misdirection and sinister clown humor"  
[YouTube Link](https://youtube.com/watch?v=444XYfvp6ww)  2025-12-30T05:35Z 20.2K followers, 18.8K engagements


"Orlando Funnybone"  
[YouTube Link](https://youtube.com/watch?v=GBNpzXZozaw)  2025-12-28T06:29Z 20.2K followers, [----] engagements


"Smoking Baby"  
[YouTube Link](https://youtube.com/watch?v=H7X_umbPlrA)  2025-12-25T03:34Z 20.2K followers, [----] engagements


"This isn't good"  
[YouTube Link](https://youtube.com/watch?v=XcF3oDIABXM)  2025-12-21T22:58Z 20.2K followers, 11.8K engagements


"Olive Garden B.S"  
[YouTube Link](https://youtube.com/watch?v=QtGTsMYSsGI)  2025-12-21T06:28Z 20.2K followers, [----] engagements


"Car Trouble"  
[YouTube Link](https://youtube.com/watch?v=0mJO2SAkG48)  2025-12-17T07:40Z 20.2K followers, [----] engagements


"Firehouse Baby"  
[YouTube Link](https://youtube.com/watch?v=vzL4L14HBvY)  2025-12-09T06:20Z 20.2K followers, [----] engagements

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