Reilly first played with the Long Island hardcore band Confide,[1] featuring Gregory Catanese of Forklift Driver. Reilly described the sound of Confide as "Tripface fighting One4One in an alley behind a laundromat while Snapcase tried to break it up." After Confide disbanded due to the music going in a more emotional style, Reilly joined up and helped form The Rookie Lot. The band played locally and released a demo tape, as well as a split 7" with fellow Long Islanders, Yearly. The Rookie Lot dissolved, seeing Reilly join The Movielife[1] as the lead guitarist whilst other members formed the band Brand New. After The Movielife broke up he formed Nightmare of You,[2] an indie pop act. He began writing his own songs while still in The Movielife. Before beginning Nightmare of You he had never done vocals; he was admittedly "a little scared" of singing and thought his voice was "not tempered to be a vocalist, especially not a lead vocalist."