Why? used to be a rapper who never really fit in; he writes lines such as “I’m not gay/But I do like to know just who’s at the park throwing frisbee with their shirts off.” After getting his start when he found his first four-track in the basement of his father’s synagogue, Why? transitioned from rapper to folk singer with sounds like Daniel Johnston’s—if Johnston had a larger budget and B-boy aspirations. Why? is a man who knows how to push pleasure centers: His new album, Elephant Eyelashes, features simple, infectious guitar melodies that give way to sudden shifts and swirling soundscapes. This new release is a tribute to Why?’s skill and vulnerability as a songwriter—and to the talent of his new ensemble, which takes the songs past the musings of a bedroom impresario to those of a full-on, geeked-out rock band. Why? plays with the Islands and Cadence Weapon at 8:30 at the Black Cat’s Mainstage, 1811 14th St. NW. $12. (202) 667-7960. (Doug Tye)