80s and 90s vs 00s and 10s

A battle between pop-cultural characters from everybody's childhoods of the 1980s, 1990s, 2000s, and 2010s will take place, in the biggest battle of the century. I'll make matchups later...

1980s and 1990s

 * Optimus Prime (Transformers)
 * Bananaman (Bananaman)
 * Inspector Gadget (Inspector Gadget)
 * He-Man (Masters of the Universe)
 * SuperTed (SuperTed)
 * Voltron (Voltron: Defender of the Universe)
 * Lion-O, Snarf, Panthro, Cheetara, Tygra, Wilykit & Wilykat (Thundercats)
 * Pee-Wee Herman (Pee-Wee's Playhouse)
 * Slimer (The Real Ghostbusters)
 * Leonardo, Ralphael, Donatello, and Michelangelo (Teenage Mutant Ninja Turtles)
 * Mario and Luigi (Super Mario Bros.)
 * Samus Aran (Metroid)
 * Ryu and Chun-Li (Street Fighter)
 * Link (The Legend of Zelda)
 * Megaman (Megaman)
 * Gavan (Space Sheriff Gavan)
 * Robocop (Robocop)
 * Homer Simpson (The Simpsons)
 * The Mask (The Mask)
 * Captain Planet (Captain Planet and the Planeteers)
 * Tommy Pickles, Chuckie Finster, Phil and Lil Deville, and Suzie Charmichael (Rugrats)
 * Red, Black, Blue, Yellow, and Pink Rangers (Mighty Morphin Power Rangers)
 * Yakko, Wakko, and Dot (Animaniacs)
 * The Tick (The Tick)
 * Goliath (Gargoyles)
 * Brain and Pinky (Pinky and the Brain)
 * Sailor Moon, Sailor Mercury, Sailor Mars, Sailor Jupiter, and Sailor Venus (Sailor Moon)
 * Woody and Buzz Lightyear (Toy Story)
 * Dexter (Dexter's Laboratory)
 * Goku (Dragon Ball Z)
 * Johnny Bravo (Johnny Bravo)
 * Pikachu (Pokémon)
 * Blossom, Bubbles, and Buttercup (The Powerpuff Girls)
 * SpongeBob (SpongeBob SquarePants)
 * Agumon (Digimon)
 * Big Guy and Rusty (Big Guy and Rusty the Boy Robot)
 * Sonic and Tails (Sonic the Hedgehog)
 * Captain Falcon (F-Zero)
 * Kirby (Kirby's Dreamland)
 * Barney (Barney and Friends)
 * Fox McCloud (Star Fox)
 * Johnny Cage, Liu Kang, & Sonya Blade (Mortal Kombat)
 * Savage Dragon (Savage Dragon)
 * Marshal Bravestarr (Bravestarr)
 * Saber Rider (Saber Rider and the Star Sheriffs)
 * Zachary Foxx, Shane Gooseman, Niko, Walter Hartford (Adventures of the Galaxy Rangers)
 * Galtar (Galtar and the Golden Lance)
 * Princess Gwenevere (Princess Gwenevere and the Jewel Riders)
 * Kenshiro (Fist of the North Star)
 * Vytor (Vytor: the Starfire Champion)
 * Denver (Denver the Last Dinosaur)
 * Esteban, Zia, & Tao (Mysterious Cities of Gold)
 * Pac-Man (Pac-Man)
 * Cybersix (Cybersix)
 * Bucky O'Hare (Bucky O'Hare and the Toad Menace)
 * The Toxic Avenger (The Toxic Avenger)
 * Big Pete Wrigley & Little Pete Wrigley (The Adventures of Pete & Pete)
 * Spartan (WildC.A.T.S.)
 * The Maxx (The Maxx)
 * Dimitri Maximoff & Morrigan Aensland (Darkstalkers)
 * Throttle, Modo, and Vinnie (Biker Mice from Mars)
 * Prince Lightstar (Skeleton Warriors)
 * Questar (Dino-Riders)
 * Scrooge McDuck (Ducktales)

2000s and 2010s:

 * Yang (Yin Yang Yo!)
 * XXXG-00W0 Wing Gundam Zero (Mobile Suit Gundam Wing)
 * Pucca and Garu (Pucca: Funny Love)
 * Timmy, Cosmo, and Wanda (The Fairly Oddparents)
 * Samurai Jack (Samurai Jack)
 * Medabee (Medabots)
 * Yugi (Yu-Gi-Oh!)
 * Garrius (Zoids: Chaotic Century)
 * Yusuke Urameshi (YuYu Hakusho)
 * Hamtaro (Hamtaro)
 * Kim Possible and Ron Stoppable (Kim Possible)
 * Tyson (Beyblade)
 * Jimmy Neutron, Carl Wheezer, and Goddard (Jimmy Neutron: Boy Genius)
 * Ruroni (Ruroni Kenshin: Wandering Samurai)
 * XJ-9 (My Life as a Teenage Robot)
 * Danny Phantom, Sam Manson, and Tucker Foley (Danny Phantom)
 * Bloo and Mac (Foster's Home For Imaginary Friends)
 * Atomic Betty (Atomic Betty)
 * Chiro (Super Robot Monkey Team Hyperforce Go!)
 * Will, Irma, Taranee, Cornelia, and Hey Lin (W.I.T.C.H.)
 * Aang, Katara, Sokka, Appa, and Momo (Avatar: The Last Airbender)
 * Naruto (Naruto)
 * Johnny Test (Johnny Test)
 * Ben Tennyson and Gwen Tennyson (Ben 10)
 * Robotboy (Robotboy)
 * Yin (Yin Yang Yo!)
 * Maxxor (Chaotic)
 * Chowder (Chowder)
 * Dan and Drago (Bakugan)
 * Kick Buttowski (Kick Buttowski: Suburban Daredevil)
 * Orange (Annoying Orange)
 * Finn and Jake (Adventure Time)
 * Mordecai and Rigby (Regular Show)
 * Gingka (Beyblade: Metal Saga)
 * Dudley Puppy and Kitty Katswell (T.U.F.F. Puppy)
 * Dan (Dan Vs.)
 * Gumball and Darwin (The Amazing World of Gumball)
 * Randy Cunningham (Randy Cunningham: 9th Grade Ninja)
 * Dipper and Mabel (Gravity Falls)
 * Wonder and Sylvia (Wonder Over Yonder)
 * Sora (Kingdom Hearts)
 * Dante Vale (Huntik: Secrets and Seekeres)
 * Kratos (God of War)
 * Zach Saturday Doc Saturday, Drew Saturday, Fiskerton, Komodo, & Zon (The Secret Saturdays)
 * Edward Elric, and Alphonse Elric (Fullmetal Alchemist)
 * Generator Rex (Generator Rex)
 * Ky Stax, Maya, and Boomer (Redakai: Conquer the Kairu)
 * Ranga the Bloodedge (Blazblue)
 * Adam Jensen (Deus Ex: Human Revolution)
 * Madoka Kaname (Puella Magi Madoka Magica)
 * Ezio Auditore da Firenze (Assassin's Creed)
 * Vampi (Vampi)
 * Nina, Alanis, & Samanya (Neverminds)
 * Oishi Kawaii (Oishi High School Battle)
 * El Chavo, Don Ramon, Quico, Nono, Dona Florinda, Professor Jirafales, Popis, Senor Barriga, Dona Cleotilde (El Chavo Animado)
 * Kirito & Asuna (Sword Art Online)
 * Master Shake, Frylock, & Meatwad (Aqua Teen Hunger Force)
 * Dragonborn (The Elder Scrolls V: Skyrim)
 * Katniss Everdeen (The Hunger Games)
 * Firebreather (Firebreather)
 * War (Darksiders)
 * Yoko Littner (Tengen Toppa Gurren Lagann)
 * Sol Badguy (Guilty Gear X)
 * Max, Caruso, Fiona, Rodger, and Buzz (Dinosquad)
 * Ichigo Momomiya (Tokyo Mew Mew)
 * Lin Ching, Jumpy Ghostface, Mystique Sonya, & Mighty Ray (Hero: 108)
 * The Cape (The Cape)
 * Aerrow, Junko, & Starling (Storm Hawks)
 * Shoutman + Star Sword (Digimon Fusion)
 * Tintin (Hergé's The Adventures of Tintin 2011 movie adaptation)

THE VILLAIN CIRCLE:

 * Satronica (Industrial Strength Records)
 * The Collexeutioner Madman of Erased Culture
 * Megatron (Transformers)
 * Dr. Claw (Inspector Gadget)
 * Skeletor (Masters of the Universe)
 * Texas Pete (SuperTed)
 * Prince Lotor (Voltron: Defender of the Universe)
 * Mumm-Ra (Thundercats)
 * Shredder, Bebop, and Rocksteady (Teenage Mutant Ninja Turtles)
 * Bowser (Super Mario Bros.)
 * Ridley (Metroid)
 * Ganondorf (The Legend of Zelda)
 * Dr. Wily (Megaman)
 * Don Horror (Uchuu Keiji Gavan)
 * Mr. Smith (The Simpsons)
 * Angelica Pickles (Rugrats)
 * Rita Repulsa (Mighty Morphin Power Rangers)
 * Queen Beryl (Sailor Moon)
 * Mandark (Dexter's Laboratory)
 * Frieza (Dragon Ball Z)
 * Jessie, James, and Meowth (Pokémon)
 * Mojo Jojo, Fuzzy Lumpkins, Him, Sedusa, and the Gangreen Gang (The Powerpuff Girls)
 * Plankton (SpongeBob SquarePants)
 * Dr. Eggman (Sonic the Hedgehog)
 * Black Shadow (F-Zero)
 * King Dedede (Kirby's Dreamland)
 * Andross (Star Fox)
 * Scorpion (Mortal Kombat)
 * Carl the Evil Cockroach Wizard (Yin Yang Yo!)
 * Tobe (Pucca: Funny Love)
 * Denzel Crocker (The Fairly Oddparents)
 * Aku (Samurai Jack)
 * Dr. Drakken and Shego (Kim Possible)
 * Professor Calamitous (The Adventures of Jimmy Neutron)
 * Vlad Plasmius, Lunch Lady Ghost, Technus, Skulker, Ember, Spectra, and Undergrowth (Danny Phantom)
 * Maximus I.Q. and Minimus P.U. (Atomic Betty)
 * Skeleton King (Super Robot Monkey Team Hyperforce Go!)
 * Prince Phobos (W.I.T.C.H.)
 * Fire Lord Ozai and Princess Azula (Avatar: The Last Airbender)
 * Orochimaru (Naruto)
 * Brain Freezer (Johnny Test)
 * Vilgax (Ben 10)
 * Eradicus (Yin Yang Yo!)
 * Lord Van Bloot (Chaotic)
 * Naga (Bakugan)
 * Grapefruit (Annoying Orange)
 * Ice King (Adventure Time)
 * Verminious Snaptrap, Larry, and Chameleon (T.U.F.F. Puppy)
 * Bobert (The Amazing World of Gumball)
 * The Sorcerer (Randy Cunningham: 9th Grade Ninja)
 * Lil' Gideon (Gravity Falls)
 * Lord Hater (Wander Over Yonder)
 * Xenmas (Kingdom Hearts)
 * Shao Kahn (Mortal Kombat)
 * Overlord, & Cyberface (Savage Dragon)
 * Tex Hex (Bravestarr)
 * Nemesis & Jesse Blue (Saber Rider and the Star Sheriffs)
 * Captain Kidd, & Lazarus Slade (Adventures of the Galaxy Rangers)
 * Lord Tormak (Galtar and the Golden Lance)
 * Lady Kale (Princess Gwenevere and the Jewel Riders)
 * Souther (Fist of the North Star)
 * Myzor (Vytor: The Starfire Champion)
 * Dr. Von Reichter (Cybersix)
 * KOMPLEX (Bucky O'Hare and the Toad Menace)
 * Lord Helspont (WildC.A.T.S./DC Comics)
 * Mr. Gone (The Maxx)
 * Jedah Dohma (Darkstalkers)
 * Lawrence Limburger (Biker Mice from Mars)
 * Baron Dark (Skeleton Warriors)
 * Krulos (Dino-Riders)
 * Magica De Spell and The Beagle Boys (Ducktales)
 * The Professor, & DeFoe (Huntik: Secrets and Seekers)
 * Zeus, & Thanatos (God of War)
 * V. V. Argost (The Secret Saturdays)
 * Lust, Gluttony, & Envy (Fullmetal Alchemist)
 * Van Kleiss (Generator Rex)
 * Yuuki Terumi (Blazblue)
 * Lokar (Redakai: Conquer the Kairu)
 * Shinkawa Shoichi/Red-Eye XaXa (Sword Art Online)
 * Ignignokt & Err (Aqua Teen Hunger Force)
 * Lordgenome (Tengen Toppa Gurren Lagann)
 * Ramlethal Valentine (Guilty Gear)
 * Victor Veloci (Dinosquad)
 * Highroller (Hero: 108)
 * Kish (Tokyo Mew Mew)
 * Scales (The Cape)
 * Tactimon (Digimon Fusion)
 * Master Cyclonis,Dark Ace, & Snipe (Storm Hawks)
 * Maleficent (Disney's Sleeping Beauty)