1. Miley Cyrus
Thursday, July 29 at 8:45pm, T-Mobile stage
A former Disney Channel star who has been through a cavalcade of artistic reinventions, Cyrus has overseen inescapable pop anthems, embraced psychedelia with the Flaming Lips and—most recently—flirted explored synth-pop with punk rock flourishes on her recent album, Plastic Hearts. Her headlining Lollapalooza set promises to be as unpredictable as her output. She may swing onto the stage on a wrecking ball wearing next to nothing, show up in an eleaborate weed-themed costume or simply play the hits.