Monty Mole evolution

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Monty Mole made his first appearance in Super Mario World, originally released in Japan on November 21, 1990 for the SNES (Super Nintendo Entertainment System), where he jumped out of his hole to surprise Mario and chased Mario around.

In Super Mario 64, originally released on the Nintendo 64 in Japan on June 23, 1996, the first 3D Mario game, Monty Mole appeared in a few stages where he popped out of random holes and threw rocks at Mario.

With Super Mario Sunshine, originally released for the Nintendo GameCube in Japan on July 19, 2002, Monty Mole appeared in a tank where he shot bullet bills and threw bombs at Mario. In order to defeat the Monty Mole, Mario had to throw three of the Monty Mole's bombs back at the Monty Mole.

 With Super Mario Bros. 3's "advance" remake on the GameBoy Advance, originally released in Japan on July 11, 2003, Monty Mole was a new enemy to the game, taking on Super Mario World's style.

In the New Super Mario Bros. game, originally released in North America on May 15, 2006 for the Nintendo DS, Monty Mole appeared as the boss of world 6, where he took a form similar to that of Super Mario Sunshine, where he appears in a tank, throws bombs, and shoots bullet bills at Mario, except this time in 2D. To defeat the Monty Mole, Mario has to jump on the mole three times, fire at the Monty Mole until he gets defeated, or Mario has to smash the Monty Mole with a mega mushroom.

There was also a whack-a-mole minigame where you whacked as many Monty Moles as you can before the time runs out.

In Super Mario Galaxy, originally released in Japan on November 1, 2007 on the Nintendo Wii, Monty Mole appeared with the name of Major Burrows, where he has a spiked hat and digs around the planet trying to defeat Mario. In order to defeat Major Burrows, Mario has to spin at the mole when he pokes out of the ground, and when the mole starts running away Mario has to spin at him again. Once Mario does this three times he will defeat the mole.

In Mario Kart Wii, originally released in Japan on April 10, 2008 for the Nintendo Wii, Monty Moles appear in a few levels, including Moo Moo Meadows,  where they jump out of random spots to surprise the player. 

In New Super Mario Bros. Wii, originally released in Australia on November 11, 2009 for the Nintendo Wii, Monty Mole regained his Super Mario World attack. 

Monty Moles make their appearance in New Super Mario Bros. Wii in World 6-4.

With Super Mario Galaxy 2, originally released in North America for the Nintendo Wii on May 23, 2010, Monty Mole has the exact same attacks as in Super Mario Galaxy.

In Super Mario 3D Land, originally released in Japan on November 3, 2011 for the Nintendo 3DS, Monty Moles jump out of their holes and walk back and forth.

With New Super Mario Bros. U, originally released in North America for the Nintendo Wii U on November 18, 2012, Monty Moles use their Super Mario World attack to try to defeat Mario.

In New Super Luigi U, originally released as a DLC in Japan on June 19, 2013 on the Nintendo Wii U, Monty Moles use their New Super Mario Bros. U attack.

In Mario Kart 8, originally released in Japan on May 29, 2014 for the Nintendo Wii U, Monty Moles appear in Moo Moo Meadows (Wii), where they jump out of random spots to surprise the player.

In Mario Party 10, originally released in Japan on March 12, 2015 for the Nintendo Wii U, Monty Mole Appears in a hot air balloon. In order to defeat the Monty Mole, you run through mazes in order to use different cannons to damage the Monty Mole depending on how fast you get through the maze.

In Super Mario Maker, originally released in Japan for the Nintendo Wii U on September 10, 2015, if you shake a Rocky Wrench, it will turn into a Monty Mole.

In Super Mario Maker, Monty Moles use Super Mario World's classic attack method.

In Mario Kart 8 Deluxe, released worldwide on April 28, 2017 for the Nintendo Switch, Monty Moles appear in Moo Moo Meadows (Wii), where they jump out of random spots to surprise the player.

In Super Mario Party, originally released worldwide on October 5, 2018 for the Nintendo Switch, Monty Mole makes his first playable character appearance in the Mario Party series.

In Super Mario Maker 2, originally released worldwide on June 28, 2019 for the Nintendo Switch, Monty Moles are a sprite in the menu.

In Super Mario Maker 2, Monty Moles use their Super Mario World attack.

In Mario Kart Tour, released exclusively in the USA on September 25, 2019 for Android and iOS phones, Monty Moles appear in various levels, where they jump out of random spots in the ground and fall back into the ground. However, in 2020, Monty Mole became a playable character in the game.

In Paper Mario: The Origami King, released worldwide on July 17, 2020 for the Nintendo Switch, a Monty Mole appears auctioning a shell stone on Overlook Mountain, and they later appear in Breezy Tunnel.

In Super Mario 3D All-Stars, released worldwide on September 18, 2020 on the Nintendo Switch, Monty Moles appear in all three games: Super Mario 64 (Where he popped out of random holes and threw rocks at Mario), Super Mario Sunshine (Where He appears in a tank), and in Super Mario Galaxy (Major Burrows).