Always used complimentary, unless used by someone who has poor grammar and does not know that the superlative form of "bad" is "worst".
Ironically, "baddest" and "worst" are complete opposites, despite the fact that at first glance, they appear to be synonyms.
Don't mess with Harold, he's the baddest one here!
Supreme in status or standing. The very best at something. The Ultimate Champion or Warrior. Ultimate Title or Crown. The Highest Honor. The Greatest.
The Champion of the World is the baddest dude out there. The baddest dude is second to none.
urban synonym for 'the worst'; alternatively it may mean the best.
1. da baddest book-keeper
A woman who is in control of herself and her sexuality or a sexually domineering woman.
A woman who is proficient at sensual and sexual acts.
Watch out for her, she is a baddest.
Wrong slang to say "the worst".
You be the baddest here!