As has become tradition at this point, first the Honorable Mentions:
GOGGLES (S1) - They do nothing. Needless to say, that's better than a few of the items out there.
EGGMAN (S2/S3/S&K) - Not so much on the S3/S&K side of things (though even there it has at least one accessibility purpose, for Knuckles in Lava Reef 2), but in S2 (where it's a 2P-only item) it's better than Goggles were in S1 since at least you get the item box point and a chance to inflate your Total Ring stat.
FLAME SHIELD (S3/S&K/S3D) - Useful for picking fights with Alondite, or whomever the punching bag of the month may be.
SHRINK (KC) - Frustrating yakuzas the world over since at least August 2008, and probably even earlier.
And the dishonorable mentions:
BLANK ITEM BOX (S1/S3/S&K/SA2(B)) - what a waste of space and material
LEAD SHOE (S3) - There are detrimental items that have their esoteric good points, and then there's the Lead Shoe. Simply terrible.
WETFLAME (S1WTFLAME) - You just lost The Game.
RANDOM RING (SA(DX)/SA2B/SH/a bunch of Advance and Rush games and maybe more I overlooked) - Really. No item box has ever garnered more hate from TSC over the years.
And finally, our feature presentation.
TOP TEN ITEM BOXES #1: S (SCD/S3/S&K) 
What could be a better insignia of TSC than speed? Overall superiority. Enough said.
See you back here in 173 days when two more contestants will try their hand at Building a Crappy List! How much more room can there be to do worse?
