[1][2] He started his music career with various rock bands near his hometown of Libertyville, Illinois, playing guitar for groups such as The Drovers in the late 1980s.

"[3] David Carr of the New York Times said, “Ike Reilly is a kind of natural resource, mined from the bedrock of music.

[citation needed] It was in middle school that he started writing songs and became adept at playing the harmonica, booking his first paying gig at age 13.

[1] Reilly learned to play guitar while working at Ascension Catholic Cemetery, a job he held every summer through high school and college.

[7] Following high school, Reilly attended Marquette University in Milwaukee, Wisconsin where he majored in Theology and enrolled in the Marine Corps.

He subsequently founded the band Community 9,[3] with bandmates such as Mars Williams (Liquid Soul, The Psychedelic Furs, The Waitresses) Phil Karnats (Secret Machines, Tripping Daisy), and Aidan O'Toole (The Muck Brothers).

Reilly pursued alternate paths after leaving his work at the Hyatt, becoming a freelance production assistant and, in 1997, opened the Diamond City recording studio with engineer Blaise Barton.

[7] After taking a musical hiatus, Reilly continued to write songs and started recording in 1998 with engineer Ed Tinley, who had worked with Liz Phair, Smashing Pumpkins, and R. Kelly.

“This marked the first time Reilly recorded without a band, depending more on samples and loops, starting with an acoustic take and then "building the song out.

[10] After a five-year gap, Reilly's seventh studio album Born on Fire was released in June 2015, again through Rock Ridge Music.

"[12] Popmatters wrote that "Reilly’s sonic indelibility only remains second fiddle to his astounding ability to craft a personal story and envelop it in song,"[13] while American Songwriter gave it 4/5 stars, calling it "pure, unaffected and raw" and praising his "skewed, dry, self-effacing humor.