Annie Zaleski

On Aug. 24, 2013, Florida Georgia Line's "Cruise" began its record-setting 24th week at No. 1 on the Hot Country Songs chart.

On Aug. 18, 1998, Messina landed at No. 1 on the Billboard country singles chart with "I'm Alright."

On July 30, 1983, Jones landed at No. 1 on the charts with "I Always Get Lucky With You."

Cash's late-career comeback reached another peak on July 24, 2003.

On June 30, 1993, Chesney signed his first record deal, with the newly opened country division of Capricorn Records.

On June 5, 1993, Keith earned his first No. 1 song on the Hot Country Songs Billboard chart, "Should've Been a Cowboy."

Cutest Couple? Best Comeback? They're all here ...

When Rucker first met his future wife, Beth Leonard, he was still flying high with Hootie & the Blowfish, and she was working at VH1.