Carving out a unique territory between eccentric indie-pop and classic American roots-rock, Steel Train made three albums, played most of the major festivals, and collaborated with a number of notable artists (indie heroes Amanda Palmer and Tegan & Sara, along with Dead-associated mandolinist David Grisman) during their 11-year run.

His next band Steel Train was formed in 2002 with Scott Irby-Ranniar, who later originated the role of Young Simba in The Lion King on Broadway.

Outline lasted four years as a productive DIY band, touring nationally despite the members all being in their teens Antonoff immediately loved touring and borrowed his parents' minivan to help. The second was the death of his sister Sarah from brain cancer, a tragedy that he claimed to have never fully gotten over. Two events during his teen years would be especially pivotal: One was the forming of his early punk band, Outline, when he was a sophomore in fall 1998. Raised in different parts of New Jersey, Antonoff commuted to Manhattan to attend the Professional Children's School, a renowned performing-arts high school. Famed as a member of Bleachers and Fun, Jack Antonoff also wrote hits for Taylor Swift, Sara Bareilles and Lorde.

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