Annie Zaleski

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.