Jack Ingram began his music career singing at a privately owned bar near the TCU campus of Fort Worth, Texas which was owned by his friend John Clay Wolfe. Later, during the early 1990s, His first release was the self-titled Jack Ingram in 1992 via the Rhythmic label, followed by Lonesome Question in 1995 In 1997, he released Livin' or Dyin' via Rising Tide Records, which produced his first chart single in the No. 51-peaking "Flutter". In 2005, Ingram signed to the independent record label Big Machine Records. Ingram released a predominantly live album entitled Live: Wherever You Are. His first single release on that record label, "Wherever You Are", became Ingram's first top 40, and later his first Number One single on the U.S. Billboard Hot Country Songs charts, as well as the first Number One for the Big Machine label. "Love You", the only other studio track on Live: Wherever You Are, was also released as a single, peaking at No. 12 on the charts.
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