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Description:

A new take on the classic “Dogs Playing Poker” oil painting series by C.M. Coolidge. Original (titled ‘A Friend in Need’) can be viewed here!
Edit(sorry for all the updates): Forgot to mention this; this is a relatively quick piece I threw together to help plan out an actual oil painting that I plan to do. Final product will be posted in a few weeks!
Also, I didn’t realize how controversial this would be. For clarification, I’m not classifying Iron Will as a villain. I just think the guy would enjoy a night of poker!
safe1920135 artist:joellethenose82 discord34150 gilda10445 iron will1404 king sombra15430 nightmare moon18353 queen chrysalis38348 trixie73335 alicorn264566 changeling56558 draconequus16042 griffon31822 pony1267551 unicorn420652 ace of spades81 annoyed6165 antagonist2049 chair9708 cheating184 chocolate3836 chocolate milk777 chocolate rain417 cloud36387 crown23341 dogs playing poker21 evil grin5301 eyes closed115238 female1555272 food83864 grin50077 indoors4781 interior656 jewelry86052 laughing9369 magic83760 male442063 mare588557 milk5781 nose piercing3322 open mouth187719 piercing51282 playing card670 poker402 rain6906 regalia27712 septum piercing1117 smiling315650 smirk15212 table10820 telekinesis32804 villains of equestria78

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Background Pony #52AD
Okay, this was made in 2013, and this image has Trixie included. Didn’t she redeem in Magic Duel before this was made? Couldn’t Diamond Tiara take her place instead? I mean, she herself was an antagonist before her redemption in “Crusaders of the Lost Mark”.
Background Pony #B98B
this image always annoyed me, it’s like placing Alex Jones and Ezra Miller next to Hitler and Stalin
Ardashir
My Little Pony - 1992 Edition

Chryssy and Sombra may well regret laughing at the very unamused Nightmare Moon. The look on her face says she is SO done with this.
Background Pony #3875
@DasHiveMind  
‘Constantly encouraged Dash to act like a dick’
 
Really? That’s your big claim to her being a villain?
 
Why, it’s no worse than how Spitfire encouraged Dust to act like a dick by promoting and repeatedly praising her for doing so rather than slapping her down and ensuring her training as a team player the way she was supposed to do in her position?
 
Or perhaps for villainry we should look at Dust’s reaction to everyones near death! Which is almost exactly the same as Fluttershy and Twilight’s reactions to Rarity’s near death back during the best young flyer contest… And unlike with LD the nearly dead was supposedly their best friend.
 
Or hey, do we even need to bring MMDW into this? Because we totally could and really point out how pretty much every one of the mane six can be painted as a sociopath with much less work than Lightning Dust.
 
 
Oh wait, i forgot. Doing things like that is only bad when ponies you don’t like do them.
 
Which is ultimately why most of these jerks are labelled as villains - because they just can’t bring themselves to admit that most of the ponies they like are just as bad, so they have to sling around the term ‘villain’ to make sure those mean jerkfaces are clearly segregated from their favorites (who certainly can’t be just as bad no-sir-ee whatsoever).
Minus
Princess of Love - Extra special version for those who participated in the Canterlot Wedding 10th anniversary event by contributing art.
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Philomena - For helping others attend the 2021 community collab
Twinkling Balloon - Took part in the 2021 community collab.
My Little Pony - 1992 Edition
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Dream Come True! - Participated in the MLP 9th Anniversary Event
Toola Roola - For helping others attend the 2019 Community Collab
Wallet After Summer Sale -

Feeling sick
@Grieffon  
…No-one said Gilda was not a villain here. FiM really only has 4 real villains though, but not a bad array of huge jerks. Trixie, Gilda, Diamond Tiara, and Lightning Dust all fit into the jerk category so I don’t mind them being here. It is just stupid adding in Iron Will or the Flimminy Flammers to a villain picture though. How about we add the overpriced cherry salespony as a villain too? We might as well! And in that one episode Fluttershy made her friends cry, so clearly she’s a villain too!! LET’S JUST PUT ALL THE PONIES IN THE IMAGE!!!!11 DERPIBOORUISTHEVILLAIN6ASJNSDF5A4NDGJBNSKJDB3NGKJSBGLSNETNN
 
Also it is a good image, but Sombra and discord could do with looking a bit less like vectors, facially.