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As stated on the previous page, this list is very long + silly, and some characters may be OOC (out-of-character). I had fun writing this, though!
A majority of these headcanons are about Webkinz Classic's gameplay, not the plushies or Webkinz Next. Keep in mind that if you've never played Webkinz, you probably won't understand crud here. With that being said, Webkinz Classic is almost 20 years old now (!) Also, I only included headcanons for the main and Echo fighters, not the "alternate skins". So no Koopalings, no gender variants, etc.
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Mario: Spends most of his time trying to earn Pet Medallions. He wants that Diamond Dragonfly, dangit.
Donkey Kong: Is absolutely furious that the Strength class is broken. Punched a hole into his gaming computer upon losing the Level 9 Strength class one too many times.
Link: Loves the Zums, because they remind him of Navi. Also hates the Zums, because they remind him of Navi.
Samus: Really really really hates Dex Dangerous as a character, but plays Lunar Lugbotz anyway. She spent many years thinking it was spelled "Lugboltz", with a second "L", instead of "Lugbotz".
Dark Samus: Tried to prank Samus into going on a blind date with Dex Dangerous. Samus quickly realized this "Dex" was actually Incineroar dressed up badly as a lion.
Yoshi: Voted for Sheldon Turtle in the 2014 Kinzville election. Not because of Sheldon's promise to not change anything, but because Yoshi's favorite Webkinz area is the Vacation Island.
Kirby: Knows every (discovered) Webkinz Classic stove recipe by heart. Wins every Cooking competition he enters at the Stadium, and almost every round of Chef Challenge.
Fox: The Sequin Fox is his favorite Webkinz pet. Back when Classic was playable in an actual web browser rather than the Desktop App, he used Chrome rather than Firefox.
Pikachu: His account was permabanned due to Kiwigate. He's still not over this, and never will be.
Luigi: Poor guy is absolutely terrified of the ghost from Don't Rock the Boat. Every indoor room in his Webkinz Classic house is painted solid green.
Ness: Is amazing at Wacky Zingoz, WackyER Zingoz, Wacky Zingoz Extreme, and Wacky's Bullseye Batter. He even unlocked Wacky Zingoz Extreme back in 2008, via the Code Shop.
Captain Falcon: Collects vehicles, but they keep getting stuck in doorways, so he never lets his pets ride them. Would sell his soul for a Mazin' Hamsters remake.
Jigglypuff: Often stays up literally all night playing Webkinz. Has completed every single "Learn & Play" question at Quizzy's, but her average question-score is only 3 out of 5.
Peach: Doesn't play the game, but is a serious Webkinz plush collector. Owns a Cheeky Cat and a Cheeky Dog.
Daisy: Somehow beat Level 10 of Strength class, just for the Webkinz Rally stats. Now, if only she could finish Level 10 of Agility class...
Bowser: Got into the game because of Bowser Jr and the Koopalings. Now he's addicted, and spends at least a hundred bucks on the eStore every month.
Ice Climbers: They were both devastated when the Arcade version of Polar Plunge was "remade". Popo really wants to learn to how play Waddell's Icecap Adventure, but he can't figure out the darn controls.
Sheik: Her username is misspelled as "Shiek". Has beaten Zacky's Quest four times.
Zelda: Uses up all her attempts for every game in the Magical Forest, every single day. She doesn't even care about the lag.
Doctor Mario: Voted for Daisy Doe in the 2014 Kinzville election, and immediately accused Wario of rigging the election via alt accounts when she lost. Openly ships Dr. Quack with Mrs. Birdy.
Pichu: His game keeps crashing whenever something good happens to him. It's currently unknown if this is the fault of Webkinz, Pichu, or the unstable WiFi in Pichu's room.
Falco: Used to obsessively play Webkinz, but lost interest after a few years. He now obsessively plays Neopets instead.
Marth: Owns multiple of every single Rare Item. Refuses to pay for a Deluxe Membership, because he thinks it's greedy.
Lucina: Her account was hacked, because she used an insecure password "manager" back before the Desktop App. She doesn't have the heart to play Webkinz anymore...
Young Link: Usually only plays Webkinz via the Next and Classic mobile apps. Was surprised to find out that there's more to Webkinz Classic than room-decorating, shopping, and a few mobile-app compatible minigames.
Ganondorf: Claimed that Webkinz was childish, and he would never ever play it, but Jigglypuff soon caught him playing Flutterbugged after midnight in a basement closet... on Jigglypuff's laptop. And on her account, too.
Mewtwo: Even his immense psychic powers aren't strong enough to let him cheat at the Jellybean Challenge. They do, however, let him easily cheat at Jumbleberry Fields.
Roy: His Classic account is a Free account, but he gets enjoyment out of the game anyway. Somehow.
Chrom: Ragequit the game after being scammed in the Trading Room. Can't delete his account, because he forgot the password. He used Firefox rather than Chrome to play Webkinz.
Mr. Game & Watch: Doesn't play Webkinz Classic, because even the outdated early 2000s Flash code isn't slow enough for his limited animation style to use the controls. However, he loves the Pet of the Month songs.
Meta Knight: Joined Webkinz literally last week. Kirby is giving him unwanted tips on how to earn KinzCash and decorate rooms.
Pit: Doesn't log on very often anymore, so he gave Palutena his password. She'd better not mess this up, because Pit has some VERY rare items and pets...
Dark Pit: Hasn't logged on in five months, but refuses to trust Palutena with his password. One of his two pets is a Midnight Monster named Darkness.
Zero Suit Samus: Collects vehicles, but unlike Captain Falcon, she doesn't mind them getting stuck in doors. Ganz Customer Support is swamped with her emails about that problem, however.
Wario: Only cares about earning KinzCash and mining for gems. Has completed his gem collection eight times over, but has not yet traded for the Crown of Wonder.
Snake: Was banned from KinzChat Plus for trying to swear. Only joined Webkinz because he kept mishearing it as "Weapons".
Ike: Has a massive crush on Arte. Tips him 100 KinzCash every day.
Pokemon Trainer: Squirtle often falls asleep on top of his low-end computer while his Trainer plays Webkinz Classic, because the poor code optimization makes the cooling fans run hard. Ivysaur loves helping decorate outdoor and treetop rooms. Charizard has his own account, that he uses solely to play Pizza Palace.
Diddy Kong: His favorite Arcade game is Bananza. Nobody has the heart to tell him about that infamous "stuck spider" glitch on Level 17 that makes the game borderline unwinnable.
Lucas: His Webkinz Classic account is stuck in the "Asian time zone". He loves the "family growing" aspect of Webkinz Next, but thinks the 3D graphics are an insult to humanity.
Sonic: Speedruns every Arcade game than can be won. He can't seem to get the hang of Eager Beaver or Quizzy's Word Challenge.
King Dedede: His free starter pet was the original Penguin pet. He named it after himself.
Olimar: Has dozens of rooms full of crops. He harvests them all manually, and may be developing carpal tunnel as a result.
Lucario: Argued with Fox over a code for the Sequin Fox. It turned out the code was already used anyway.
R.O.B: All eleven of his pets are Tinkerpups. He's had literal nightmares about the opponent-robots from Air Hockey.
Toon Link: Desperately wants to play Webkinz, but his personal computer is a Chromebook, and the Smash computer lounge is entirely Linux. Oof.
Wolf: Spent over a thousand dollars on a plush Signature Timber Wolf. It came without the code, so he lit it on fire.
Villager: Obsessed with room decorating, but has no pocket money to spend on eStore Points or a Deluxe membership. His proudest achievement is the time the official Webkinz Twitter account retweeted his fan art of PJ Collie.
Mega Man: Only plays Webkinz for the Arcade games. Cried when Bamboo Break was removed.
Wii Fit Trainer: Exercises while Webkinz Next loads. All of her pets have treadmills and trampolines in their rooms.
Rosalina and Luma: Rosalina gets the Lumas to quickly search up the answers at Quizzy's. Her favorite pet is the Midnight Martin.
Little Mac: Submitted his fursona to the 20th anniversary pet design contest. The "fursona" in question was his face and his boxing gloves badly Photoshopped onto Arte.
Greninja: Loves the Webkinz Trading Card Game, but nobody else in Smash does. Named his Magical Retriever that he got from card packs "NOT MEDALLIONED".
Mii Brawler: Vastly prefers Club Penguin, but since Club Penguin ded now, he plays Webkinz Classic to distract himself from his misery.
Mii Gunner: Her original account was deleted in the 2019 purge. She still hasn't realized Arte's name is a pun.
Mii Swordfighter: Plays Webkinz Next solely for the Dock Search feature and the Kinzville Pinball minigame.
Palutena: Writes to Ganz at least three times a day, asking for free eStore points. She hasn't had any luck so far.
PAC-MAN: Is obviously great at Pinky's Big Adventure. He would be great at Hungry Hog as well, if it didn't lag so much.
Robin: Has over 200 pets, thanks to eBay. Despite this, he only joined two years ago.
Shulk: Genuinely thinks Webkinz Next has good graphics. Names his rooms on Classic after Xenoblade 1 locations and landmarks.
Bowser Jr: Has at least 25 Webkinz Classic accounts; possibly more. Bowser refuses to give him KinzChat Plus access.
Duck Hunt: The duck and dog share an account. The duck spends all the dog's hard-earned KinzCash, and the dog sells everything back to the W-Shop. It's a vicious cycle.
Ryu: Has been trying (and failing) to get back into his childhood account. It wasn't purged, but he can't remember the dang password...
Ken: Has been scammed on Reddit at least five times by now. Three of those scams were by the same dude.
Cloud: Joined Webkinz in 2005. Plans to throw a real-life party for the 20th anniversary.
Corrin: Never got into Webkinz, because she's much too busy with The Sims 3.
Bayonetta: Wants the Party Packs back. Hates Amanda Panda with a burning fury.
Inkling: Color-codes all her rooms. Orange is for the good items, blue is for junk. Her dock is almost empty.
Ridley: His dock, conversely, is full of holiday and celebration presents that he never opened.
Simon: His pets feast entirely on birthday cake and Charm Candies.
Richter: Hates "pet requests" so much that he just lets their meters perpetually stay at 0. Has completed the treasure map from Don't Rock the Boat.
King K. Rool: Wants to beat Zingoz Pop, but can't get past Level 7. Often stays up all night with Jigglypuff, arguing over Tournament Arena games.
Isabelle: Takes her pets to the Vacation Island Spa instead of feeding them. Thinks the "pet requests" are cute.
Incineroar: Holds the Smash-universe-wide record for "most eStore items accidentally sold to the W-Shop". Names all his pets after Pokemon species.
Piranha Plant: Leans over Bowser's shoulder and rudely critiques his abilities in Tile Towers.
Joker: Is one of the few Webkinz players to have beaten Skater Kat. Not because he enjoyed the gameplay, but because he loves the background music.
Hero: Joined Webkinz Next out of curiosity, saw Mrs. Biscuits, and nope'd out right away.
Banjo & Kazooie: Are pooling their money for the next Moonlight Delight event. Surely they'll win this time, right?
Terry: Had never heard of Webkinz until he saw Ryu angsting over his lost account.
Byleth: Has completed every permanent Challenge on Classic. Her password has "FEsw0rdfight3rLOL" in it. The rest of the password is 30-something additional characters long... on both ends.
Min Min: "Anybody have a spare [insert item from 2005/2006] somewhere? I'll pay you back by babysitting your account!"
Steve: Loves the DIY Divider events. Tries to make pixel art with them, but even the biggest rooms are pretty dang small...
Sephiroth: Has voted for Dex Dangerous in every election he's been part of. Paints every indoor room in Classic solid black.
Pyra: Sleeps with a plush Whimsy Dragon. Can't seem to figure out Creativity class.
Mythra: Frequently gets "The Dog on the Front of the Tag" from KinzTunes stuck in her head for no reason.
Kazuya: Often sends his pets into Beauty Competitions wearing the most ridiculous outfits imaginable.
Sora: Sold all of his Pet-Specific Items, ages and ages ago. Nowadays, he only plays Webkinz for the aesthetic.
Master Hand: Was dared to sing the KinzTunes song "The Prettiest Pink Pony in Town" at karaoke night. And he actually did it.
Crazy Hand: Almost always wins the daily high score for Pumpkin Patch Protector. Has over five hundred pet Kooky Chameleons. Has (somehow) won the trophy for Mrs. Cowoline's Roll Call.
Tabuu: Prior to his defeat, he was notorious for scamming children in the Trading Room.
Galeem: His attack failed to affect Webkinz, because the universe itself refuses to let Webkinz die. Dex Dangerous frequently brags about this fact.
Dharkon: Thinks Atlantiles is the worst Webkinz game, solely because you aren't punished for using hints. He doesn't play Webkinz, so it is unknown why he has such a strong opinion about this.
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