The Boot Staff

On June 26, 1989, the struggling young country singer signed his first recording contract.

On June 24, 1989, Brooks made his debut on the Grand Ole Opry.

"Summertime, and the livin' is easy" -- so goes the old American standard.

On June 21, 2004, Wilson struck gold -- and platinum.

Can you pick just one?!

Whitley died at the age of 33 from alcohol poisoning.

On May 2, 1989, Black released his debut album, 'Killin' Time,' which sold more than 3 million copies and spawned five No. 1 hits.

On April 14, 2008, the TV show 'Can You Duet' premiered on CMT, introducing the newly formed duo Joey + Rory.

In 1963, Buck Owens topped the country charts with "Act Naturally," which opened with the prophetic line "They're gonna put me in the movies." But decades before that tune was a hit, country stars were already trading the concert stage for the sound stage.

On April 8, 1989, "I'm No Stranger to the Rain" became Whitley's last No. 1 hit before his death from alcoholism.