At the end of the interview you asked Obama to be your homeboy, and he said yes.
From the time.com
So it comes as no surprise that another Modena homeboy has set up business here.
From the metro.co.uk
Homeboy Industries has been featured on CBS News'60 Minutes and other media outlets.
From the usatoday.com
Our homeboy, North Carolina senator John Edwards, is on Kerry's short list.
From the newsobserver.com
Homeboy Industries found her a job as a production assistant in Hollywood.
From the usatoday.com
What next, men in either homeboy pressed khakis or uncles in guabayeras?
From the latimes.com
When he signs autographs, and the classy homeboy will no doubt mingle, what do you say?
From the omaha.com
The homeboy is a living legend and he can't get a standing O in Oaktown?
From the sfgate.com
If homeboy happens to see this tweet, he will be sweetly intrigued.
From the cnn.com
More examples
A fellow male member of a youth gang
A male friend from your neighborhood or hometown
Home Boy is a morning talkshow hosted by Boy Abunda whichs airs on ABS-CBN. Homeboy presents a dynamic discussion of real stories through actual interaction between Boy Abunda as host, his celebrity guests and his live studio audience.
Homeboy is a 1988 drama film, directed by Michael Seresin. It was written by and stars Mickey Rourke in the role of self-destructive cowboy/boxer Johnny Walker. ...
Homeboys is the third album by alternative rock band Adam Again.
(The Homeboys (Oz)) The Homeboys are the African American prisoners of Oz associated with the drug dealing business. As 78% of Oz's prisoners are black (and most non-Muslim), they have more soldiers than any other prison gang in Oz.
Means a friend, usually of the male persuasion. Homegirl is used to refer to a friend who is a girl.
Used in the early 80's to describe someone who is a gang banger.