| Image | Info | Created | Appearances | What's Changed?
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| First Poopsmith | 1999 | Marshmallow's Last Stand | N/A
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| Second Poopsmith | 2000 | The King of Town (Old version), Yearbook Character Page (in photo) | His head has turned slighly, he has a thicker outline and slightly thicker hair, the poop on his gloves is now brown instead of green, his lip doesn't stick out as much, and he has less shading.
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| Third Poopsmith | 2000 | A Jumping Jack Contest | His outlines are thinner, no poop on his feet, and greener poop on hs gloves.
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| Fourth Poopsmith | ??? | The King of Town (New version) | He has a coloured outline, more shading, and his head has turned a bit more.
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| Transitionary Poopsmith | 2000 | A Holiday Greeting, Homestarloween Party, The House That Gave Sucky Treats, Theme Song Video, The Luau, The Best Decemberween Ever, Yearbook Character Page | He has white hairs, darker colours, thinner outlines and darker poop on his gloves.
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| Current Poopsmith | February 2002 | Where's The Cheat? to current | He has thin, grey hairs, darker feet and darker poop on his gloves. His larger eye has a gleam/light reflection, he has much more advanced shading and his outlines are thicker.
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