June 26, 1989, might have seemed like any other day in Nashville, but it was actually one of those watershed moments that only reveals itself in retrospect. A struggling young country singer named Alan Jackson signed his first recording contract that day -- 28 years ago today -- launching one of the most celebrated country music careers of all time. The photo above, from Jackson's private collection, shows the aspiring young singer with Tim DuBois, then-president of Arista Records, and Barry Coburn, Jackson's manager at the time.

For someone who would go on to such an auspicious career, Jackson got off to a slow start with his first single, "Blue Blooded Woman," which failed to crack the Top 40. But his next single, "Here in the Real World" -- the title song of his debut album -- reached the Top 5 and was followed by a rapid succession of hits including "Wanted," "Chasin' That Neon Rainbow" and "I'd Love You All Over Again." From there, the singer-songwriter has amassed an astonishing 50 Top 10 hits, with 35 of them reaching No. 1.

Jackson has also won two Grammy Awards, 16 CMA Awards and 17 ACM Awards. He is a member of the Georgia Music Hall of Fame and the Grand Ole Opry. In 2014, Jackson received the first-ever Impact Award at the CMT Music Awards. Fortunately for his fans, the word "retirement" doesn't seem to be in the 57-year-old's vocabulary.

“I don’t know what I’d retire from," he points out wryly. "I don’t work much now.”

This story was originally written by Sterling Whitaker, and revised by Angela Stefano.

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