Watsky’s early career as a poet has impacted everything he’s done since. Whether emotionally raw or subversively comedic, lyrically gymnastic or narrative-based, the emphasis has always been on the words. After winning the National Youth Poetry Slam at the Apollo Theater and appearing on the final season of Russell Simmons’ Def Poetry on HBO, he honed his stagecraft performing on nearly two hundred college campuses. Although he had long been releasing independent, lyrics-driven hip hop, a 2011 viral rap video boosted Watsky’s social media following and led to several talk show appearances. A relentless stream of mixtapes and videos has built Watsky’s fan base, racked up over 250 million total YouTube views, and opened the door for international headlining tours and festival appearances, including Van’s Warped Tour, Outside Lands, Bumbershoot, Soundset and Wireless. At every turn, Watsky has refused to be pigeonholed, following up his speed rap success with 2013 LP Cardboard Castles, an eccentric ode to creativity, and 2014’s Anderson. Paak-produced All You Can Do. After a hiatus to work on new material, Watsky pivots again, this time to prose, returning simultaneously with the essay collection How To Ruin Everything, published by Plume/Penguin-Random House, of which Hamilton creator Lin-Manuel Miranda writes, “funny, subversive […] you find yourself nodding your head in wonder and recognition,” and Watsky’s most ambitious album yet—Times Infinity—executive produced by early supporter Russell Simmons, co-produced by longtime collaborator Kush Mody, with additional production by Anderson .Paak and contributions from 21 Pilots drummer Josh Dun.