Boston’s making money like Billy Costigan
While Webby’s in CT grinding for Washingtons

from Chris Webby (Ft. Mac Miller) – I Need A Dollar Lyrics on Rap Genius

Meaning

Talking about “Boston’s Boy” Sam Adams, who has had more financial success than Webby because of his pop-rap songs. Billy Costigan is a character in The Departed, which also takes place in Boston.

On the other hand Webby is at his hometown of Connecticut trying to get some dollar bills together. Notice all the city/state wordplay.

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