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...waiting for someone to mention Ted Leo, and finally someone did. He is one of the best, for sure. Only problem is that as he's grown in popularity, he's been playing larger & larger venus in the San Francisco area. I still treasure the time I saw him at tiny Bottom of the Hill.
One of THE most amazing live bands in America today is Spottiswoode & His Enemies, who usually only play on the east coast -- they came to San Francisco once, and I caught them in North Carolina last year. It's a large band so it's difficult for them to travel. Beauty & drama & one of the most charismatic frontmen you'll ever see. They'll be playing in NY, MA and NC this summer.
I am not a huge folk music aficionado, but every time she tours, I go see Cheryl Wheeler. Her songs range from heartfelt & touching to laugh-out-loud hilarious, and the stories she tells between the songs are just as entertaining as her music. This is a lady who's been playing live for decades (she's in her 50s), and just keeps getting better and better.