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What bosses are hardcore
Literally anything post-WOF
And yeah, if you can fight it before fighting the Wall of Flesh, it's not Hardmode and it cannot drop dev items.
Hardmode is the stage in the game that comes after you defeat the Wall Of Flesh.
Hardcore is a character setting that basically means that character will die permanently and the character file will be sent straight to the Recycle Bin.
And to further clarify, Expert Mode is a world setting that makes the world itself more difficult to play.
So in summary, the developer sets you are looking for will be found in treasure bags dropped by Hardmode bosses, and treasure bags can only be dropped in Expert Mode. None of this has anything to do with having a Hardcore character.
EDIT: Fixed three typos and changed "loot" to "treasure."
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