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Description
Oh boy... what have I done this time? I'd better explain... this is based on a game show known as SkatoonY. If you've never heard of it, SkatoonY is a show where cartoon characters compete against live-action children on a quiz-type show that lasts three rounds. If they get ten questions right, they win a prize. During each round, however, at least two contestants are eliminated. While I've never seen SkatoonY (and to be honest, I'm not even interested in watching it at all. I probably wouldn't like the show anyway), I was first introduced to the show when I saw a few other users make images/memes based on the show, but with characters from various different shows (and sometimes movies and/or video games).

And where does this picture come in? Well, this originally started out as a mere suggestion from ChasesCreations (I was hesitant on whether or not I should accept said suggestion at first), but I decided to turn this into something even more ridiculous. Much like the original show, this picture shows various fictional characters in the famous squares. However, instead of competing against live-action kids, these guys would more likely compete against Toon villains, or perhaps the Cogs. Although SkatoonY is a show from the 2000s, I chose to use characters mainly from the 1980s and 1990s. Some of these characters are from franchises you've probably never heard of unless you were born before or during the 1980s (I only know about these franchises thanks to the Internet). I also made it so that there are two competitors (or duos) per square instead of one, because why not.

Green - Amberley the Noop (The Dreamstone) and Liz Ard (The Magic School Bus).
Red - Strawberry Shortcake (1980 version from the animated special The World of Strawberry Shortcake) and Red Butler (Rainbow Brite) (I could care less about the Strawberry Shortcake franchise, though. And knowing Red Butler, he's probably going to bore the others with one of his long-winded stories of heroism.)
Magenta/Pink - Lady Lovely Locks and Rose Petal (Rose Petal Place) (I'm not gonna lie... the flower on Rose's head was difficult to draw.)
Purple - Granny Jojo and Plum (Blue's Clues) (If you don't know who Plum is, he is a friend of Periwinkle.)
Blue - Herself the Elf (cartoon version from the 1983 special The Magic of Herself the Elf) and Grover (Yes, there's a Sesame Street character here as well.) (I also heard that, apparently, American Greetings tried to bring back Herself the Elf in 2016, but said revival never saw the light of day.)
Yellow - Riff-Raff (Heathcliff & the Catillac Cats) and Bert Raccoon (The Raccoons) (I bet Riff-Raff is less than thrilled that he got paired up with Bert, of all Toons.)

The Dreamstone and Amberley(C) Michael Jupp, Martin Gates Productions, and Monster Entertainment
The Magic School Bus and Liz(C) Scholastic, Joanna Cole, and Bruce Degen
Strawberry Shortcake (the character and the franchise)(C) WildBrain and Iconix Brand Group
The World of Strawberry Shortcake(C) Fred Wolf Films (then known as Murakami-Wolf-Swenson) and Toei Animation
Rainbow Bite and Red Butler(C) Hallmark Cards
Lady Lovely Locks(C) American Greetings (?) and Mattel
Rose Petal Place and Rose Petal(C) Ruby-Spears Productions, David Kirschner (and I kid you not; this is the same guy who would later create the infamous Chucky doll!), Worldvision Enterprises, and Kenner Products (now defunct; succeeded by Hasbro)
The New Amazing Adventures of Gumball and Granny Jojo (C) Ben Bocquelet and Nelvana
Blue's Clues and Plum(C) Traci Paige Johnson, Todd Kessler, and Angela Santomero
Herself the Elf(C) American Greetings and Mattel (the 1983 special was produced/animated by (again) Nelvana and Scholastic Entertainment.)
Sesame Street and Grover(C) Sesame Workshop
Heathcliff & the Catillac Cats and Riff-Raff(C) Creators Syndicate (and WildBrain)
The Raccoons and Bert(C) Kevin Gillis
SkatoonY(C) James Fox, Brian Boyle, Talent TV and Cartoon Network Europe (for the British version, at least. The other versions were produced by several different companies.)
Other characters and franchises mentioned above belong to their respective owners, blah blah blah... you know the rest.

Description
Oh boy... what have I done this time? I'd better explain... this is based on a game show known as SkatoonY. If you've never heard of it, SkatoonY is a show where cartoon characters compete against live-action children on a quiz-type show that lasts three rounds. If they get ten questions right, they win a prize. During each round, however, at least two contestants are eliminated. While I've never seen SkatoonY (and to be honest, I'm not even interested in watching it at all. I probably wouldn't like the show anyway), I was first introduced to the show when I saw a few other users make images/memes based on the show, but with characters from various different shows (and sometimes movies and/or video games).

And where does this picture come in? Well, this originally started out as a mere suggestion from ChasesCreations (I was hesitant on whether or not I should accept said suggestion at first), but I decided to turn this into something even more ridiculous. Much like the original show, this picture shows various fictional characters in the famous squares. However, instead of competing against live-action kids, these guys would more likely compete against Toon villains, or perhaps the Cogs. Although SkatoonY is a show from the 2000s, I chose to use characters mainly from the 1980s and 1990s. Some of these characters are from franchises you've probably never heard of unless you were born before or during the 1980s (I only know about these franchises thanks to the Internet). I also made it so that there are two competitors (or duos) per square instead of one, because why not.

Green - Amberley the Noop (The Dreamstone) and Liz Ard (The Magic School Bus).
Red - Strawberry Shortcake (1980 version from the animated special The World of Strawberry Shortcake) and Red Butler (Rainbow Brite) (I could care less about the Strawberry Shortcake franchise, though. And knowing Red Butler, he's probably going to bore the others with one of his long-winded stories of heroism.)
Magenta/Pink - Lady Lovely Locks and Rose Petal (Rose Petal Place) (I'm not gonna lie... the flower on Rose's head was difficult to draw.)
Purple - Granny Jojo and Plum (Blue's Clues) (If you don't know who Plum is, he is a friend of Periwinkle.)
Blue - Herself the Elf (cartoon version from the 1983 special The Magic of Herself the Elf) and Grover (Yes, there's a Sesame Street character here as well.) (I also heard that, apparently, American Greetings tried to bring back Herself the Elf in 2016, but said revival never saw the light of day.)
Yellow - Riff-Raff (Heathcliff & the Catillac Cats) and Bert Raccoon (The Raccoons) (I bet Riff-Raff is less than thrilled that he got paired up with Bert, of all Toons.)

The Dreamstone and Amberley(C) Michael Jupp, Martin Gates Productions, and Monster Entertainment
The Magic School Bus and Liz(C) Scholastic, Joanna Cole, and Bruce Degen
Strawberry Shortcake (the character and the franchise)(C) WildBrain and Iconix Brand Group
The World of Strawberry Shortcake(C) Fred Wolf Films (then known as Murakami-Wolf-Swenson) and Toei Animation
Rainbow Bite and Red Butler(C) Hallmark Cards
Lady Lovely Locks(C) American Greetings (?) and Mattel
Rose Petal Place and Rose Petal(C) Ruby-Spears Productions, David Kirschner (and I kid you not; this is the same guy who would later create the infamous Chucky doll!), Worldvision Enterprises, and Kenner Products (now defunct; succeeded by Hasbro)
The New Amazing Adventures of Gumball and Granny Jojo (C) Ben Bocquelet and Nelvana
Blue's Clues and Plum(C) Traci Paige Johnson, Todd Kessler, and Angela Santomero
Herself the Elf(C) American Greetings and Mattel (the 1983 special was produced/animated by (again) Nelvana and Scholastic Entertainment.)
Sesame Street and Grover(C) Sesame Workshop
Heathcliff & the Catillac Cats and Riff-Raff(C) Creators Syndicate (and WildBrain)
The Raccoons and Bert(C) Kevin Gillis
SkatoonY(C) James Fox, Brian Boyle, Talent TV and Cartoon Network Europe (for the British version, at least. The other versions were produced by several different companies.)
Other characters and franchises mentioned above belong to their respective owners, blah blah blah... you know the rest.