Macy Gray is celebrating her Grammy-winning debut by performing "On How Life Is" in its entirety for two shows at City Winery. Gray's raspy-jazzy vocals brought comparisons with Billie Holiday and Nina Simone when she emerged on the music scene in 1999, offering a different style of pop during a time when Britney Spears was finding stardom with "… Baby One More Time" and Ricky Martin was "Livin' La Vida Loca."
Why go: A glass of fine wine while listening to "Do Something," "Still," "Why Didn't You Call Me" and, of course, "I Try."
Reconsider: You were only digging the Backstreet Boys in those days.
Details: 8 p.m. Tuesday and Wednesday at City Winery, 1200 W. Randolph St.; $48-$68; 312-733-9463, citywinery.comCopyright © 2015, The Baltimore Sun