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1.
One of the coolest towns, it is located in Boston, Massachusetts it also known as "Southie".
Eddie: "South Boston is the coolest place ever!"
Jacob: "Fo' rizzle!"
by EddieMcD April 22, 2006
 
2.
South Boston is a ghetto hood where Irish gang members have ruled the streets for centuries. Housing projects, drug dealers, and homicides are a usual sight in southie.
South Boston is the poorest urban area where over 75% of the residents are white.
by Southie Irish April 18, 2010
 
3.
A small town in Southern Virginia.

It's an odd mixture of ghetto, redneck, middle-class conservatism. The poverty level is through the roof and ignorance runs rampant. The only good thing is that the cost of living in extremely low, that's about it.
Scene in South Boston:

(Rafael)- Hello, good sir. How are you today?

(Billie)- Whachu want, faggot? Get cher Obama lovin' ass outta my sight!

Typical.
by That Guy 765 May 22, 2009
 
4.
where all the cool kids live.
and where you can get stabbed on any given day.
or meet hott guys.
aka pretty much the coolest place ever.
i went to south boston and met this hott kid seamus who told me about how he got stabbed.
by WERECOOL. September 23, 2006