Southwinds is my favorite bar in Brownsville; men in cowboy hats drunkenly singing karaoke, cheap beers, pleasant and attentive waiter/waitress service for drinks, and there are never a ton of wasted young men trying to see if you'll go home with them at the end of the night.
I don't know if I can begin to explain the charm of this place. Maybe it's just more relaxed than most of the bars frequented by the 21-30 crowd in Brownsville, but this isn't to say if you're not over 30 you will be the youngest person in the bar. There are people from age 21-70 in there, but they all seem to be searching for the same relaxed bar experience peppered by hilarious karaoke performances. It would get 5 stars if it had a more consistent crowd. Best nights to go seem to be Saturday and Friday, but Wednesdays and Thursdays have been solid from time to time.