Born in Libertyville, Illinois, Michael Christopher Reilly began playing guitar as a young teenager, and formed his first band in college, at Milwaukee's Marquette University. He moved to Chicago after graduating and continued forming and playing in various bands. It was around that time when he dropped the "M" from his first name and started going by Ike.
In the early aughts, Reilly signed with Universal Records and released his debut album Salesmen and Racists in 2001. His time with the label was short-lived, though, and he eventually left to join Rock Ridge Music.
With that label transition, Reilly began performing with the band Ike Reilly Assassination. They released two albums in 2004, Sparkle in the Finish and Junkie Faithful, returning in 2007 with We Belong to the Staggering Evening.
Two more albums followed over the next two years, 2008's Poison the Hit Parade and 2009's Hard Luck Stories. Reilly took a hiatus before returning in 2015 with Born on Fire and with Crooked Love in 2018.
In 2021, Reilly released Because the Angels.