James Travis Tritt was born on February 9, 1963 in Marietta, Georgia, to James and Gwen Tritt. He first took interest in singing after his church's Sunday school choir performed "Everything Is Beautiful." He received his first guitar at age eight and taught himself how to play it; in the fourth grade, he performed "Annie's Song" and "King of the Road" for his class, and later got invited to play for other classrooms in his school. At age fourteen, his parents bought him another guitar, and he learned more songs from his uncle, Sam Lockhart.

In early 1994, after "Worth Every Mile" fell from the charts, Tritt charted at number 21 with a cover of the Eagles' "Take It Easy". He recorded this song for the tribute album Common Thread: The Songs of the Eagles (released through Warner Bros.' Giant Records division), which featured country music artists' renditions of Eagles songs. When filming the music video for this song, Tritt requested that the band, which was on hiatus at the time, appear in it. This reunion inspired the Eagles' Hell Freezes Over Tour, which began that year.  His fourth album, Ten Feet Tall and Bulletproof, was released that May. Its lead-off single, "Foolish Pride", went to number one, and the fourth single, "Tell Me I Was Dreaming", reached number two. In between these songs were the title track at number 22 and "Between an Old Memory and Me" (originally recorded by Keith Whitley) at number 11. The album included two co-writes with Gary Rossington of Lynyrd Skynyrd, and guest vocals from Waylon Jennings and Hank Williams, Jr. on the cut "Outlaws Like Us". The album achieved platinum certification in December of that year, and later became his third double-platinum album. Allmusic reviewer Brian Mansfield said that Tritt was "most comfortable with his Southern rock/outlaw mantle" on it, comparing "Foolish Pride" favorably to "Anymore" and the work of Bob Seger. Alanna Nash praised the title track and "Tell Me I Was Dreaming" in her review for Entertainment Weekly, but thought that the other songs were still too similar in sound to his previous works.  1995's Greatest Hits: From the Beginning included most of his singles to that point, as well as two new cuts: the Steve Earle composition "Sometimes She Forgets" and a cover of the pop standard "Only You (And You Alone)". The former was a top ten hit at number seven, while the latter spent only eight weeks on the country charts and peaked at number 51. Greatest Hits was certified platinum.

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