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Heres some background on Shy Guys:
"Shy Guys are timid troublemakers that wear robes and masks. They first appeared in the non-Mario game Doki Doki Panic. They originally worked for Wart in the dreamworld Subcon. The Shy Guys are common enemies in the Yoshi series. In later games, Shy Guy joins in some social activities like sports and parties."
The Shy Guy appears in too many games to list:
Super Mario Bros. 2, Super Mario Bros. 3, The Legend of Zelda: Link's Awakening, Super Mario World 2: Yoshi's Island, Super Mario RPG: Legend of the Seven Stars, Tetris Attack, Super Mario 64, Yoshi's Story, The Legend of Zelda: Link's Awakening DX, Mario Party, Mario Party 2, Mario Tennis, Paper Mario, Mario Party 3, Super Mario Advance, Luigi's Mansion, Yoshi's Island: Super Mario Advance 3, Mario Party 4, Mario Party-e, Mario Party 5, Mario Kart: Double Dash, Mario & Luigi: Superstar Saga, Paper Mario: The Thousand-Year Door, Mario Power Tennis, Super Mario 64 DS, Mario Party 6, Yoshi Touch & Go, Mario Party Advance, Mario Superstar Baseball, Mario Party 7, Mario Kart DS, New Super Mario Bros., Yoshi's Island DS, Super Paper Mario, Mario Party 8, Mario Strikers Charged, Mario & Sonic at the Olympic Games, Super Mario Galaxy, Mario Party DS, Super Smash Bros. Brawl, Mario Kart Wii, Mario Super Sluggers, Yume Kojo: Doki Doki Panic.
See, I probably missed a couple there.
Anyways, I made this video for obvious reasons... I was thinking about what Shy Guys look like under the mask and decided to come up with my own interpretation of whats under the mask(it's not their official real faces, sorry.)