PokéBase - Pokémon Q&A
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If a Pokémon is obtained at a level above 100 (101-254), it can be
leveled up with Rare Candies up to level 255. If a Rare Candy is fed
to a level 255 Pokémon, its level will reset to 0. If a Pokémon above
level 100 levels up due to experience, its level will be reset to 100.

Is there a way to get Level 255 Pokémon in GSC? You are limited to Rare Candies. Right?

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Perhaps more importantly, how do you plan on obtaining a Pokemon at a level above 100?

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If a Pokémon is obtained at a level above 100 (101-254), it can be leveled up with Rare Candies up to level 255. If a Rare Candy is fed to a level 255 Pokémon, its level will reset to 0. If a Pokémon above level 100 levels up due to experience, its level will be reset to 100.

Source

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How do you get 155 Rare Candies?
https://bulbapedia.bulbagarden.net/wiki/Rare_Candy

Finite: Routes 27, 28, and 34, Violet City, Tin Tower, Glitter Lighthouse, Whirl Islands, Mt. Mortar, Lake of Rage, Vermilion City, Cinnabar Island

Repeatable: Goldenrod Radio Tower (3 Blue Card points) (only in Crystal), Pokémon Pikachu 2 GS (999 watts)