Usually means: Authority figure, often colloquially respected.
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We found 7 dictionaries that define the word bossman:

General (6 matching dictionaries)
  1. bossman: Oxford Learner's Dictionaries
  2. Bossman, bossman: Wordnik
  3. bossman: Wiktionary
  4. bossman: Infoplease Dictionary
  5. bossman: Dictionary.com
  6. Bossman (artist), Bossman (rapper), Bossman (song), Bossman (wrestler): Wikipedia, the Free Encyclopedia

Slang (1 matching dictionary)
  1. Bossman: Urban Dictionary

Definitions from Wiktionary (bossman)

noun:  (often mildly derogatory) A male boss or employer.
noun:  (vocative)
noun:  Used as a term of address for an unfamiliar, possibly distrusted man: bud, buddy, friend.
noun:  Used as a term of address for a man who appears courageous: boss.

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