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1.
Toughest, coolest.

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!
by Rodney Basil July 10, 2004
217 49
 
2.
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.
by Reverend Thabiti November 28, 2005
96 28
 
3.
urban synonym for 'the worst'; alternatively it may mean the best.
1. da baddest book-keeper
by dabaddestguy July 05, 2009
33 44
 
4.
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.
by sketchokiri July 21, 2009
17 41
 
5.
Wrong slang to say "the worst".
You be the baddest here!
by Fangsta December 15, 2003
17 94