Iconoclastic rapper Kool Keith brings his Punk Rap Tour into Will’s Pub this week

In a pop world where everyone wants to appear at least a little outré (as long as it doesn’t impact the bottom line), the enduring non-career of iconoclastic rapper Kool Keith is always inspiring.

First gaining fame as part of the boundary-pushing collective Ultramagnetic MCs in the 1980s, soon enough he struck out on his own and it was off to the races. His discography is almost unrivaled in its depth, featuring collaborations with everyone from Ice T to Del the Funky Homosapien to Thetan, and his infamous and iconic turn as Dr. Octagon singlehandedly remade trip-hop in his own weirdo image.

He’s still doing whatever he wants, and he’s returning to Orlando’s Will’s Pub, a city and a stage where he has deep connections going back years. Joining Kool Keith on this tour is the equally iconoclastic MC Homeless, a Midwest rapper who effortlessly fuses hardcore fury, industrial blasts and impeccable bars. Last time through he played Grumpy’s with Black Wick and a lot of you missed it, so don’t repeat that mistake.

8 p.m. Friday, April 18, Will’s Pub, $20-$25.

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This article appears in Apr 16-22, 2025.