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  1. Ironicaly In the Early 80's it was used as an INSULT to someone who didnt hang out on the streets and stayed home alot or wasnt cool at all(at least in the bronx thats how it was used). Calling someone a Homeboy back then would get you in a fight.
  2. By the Mid-80's it was suddenly reversed from an insult to a compliment you used to describe someone who was a good friend!!! Amazing! I remember the transitional phase when people would call someone their "homeboy" in a friendly manner and the person who remembered the old meaning would get pissed off. So funny.
  3. A respected friend or associate.
  4. A principle term of reference for individuals with a peaceful gang affiliation.

You can take the boy out the hood, but you cant take the hood out the homeboy -- The Comrads (Homeboyz) [1]