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Answer:
ILLEST
Possible Questions:
Most in need of a doctor
Sickbay superlative
Most cool, in slang
Least healthy
Least well
Least hale
Most unwell
Least sound
Superlatively phat
Most sickly
Greenest around the gills
Coolest, in rap slang
Best, at the skatepark
'80s rappers all tried to be this