Top Definition
The area of Milwaukee, Wisconsin located south of Oklahoma Avenue on the city's south side. It is called the "Deep South" because it is predominantly white and has a reputation for being racist and intolerant towards the LGBT community. Many residents (in other parts of city) consider it a suburb that happens to be within in the city limits and describe it as being 20 years behind the rest of Milwaukee. In spite of being a relatively small area, it is often (incorrectly) thought of as being "typical" of the entire city, and thus, is most likely the reason Milwaukee gets stereotyped as a stodgy, backwards town.
"You been to the Deep South Side?"

"Yea, no wonder people think such f***ed up things about Milwaukee. That place is just like being upstate, only with a lot more people... it should be bulldozed into the lake."
by illwauk October 07, 2007
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