Twenty-four years ago today (Sept. 29, 1993), Vince Gill was doing plenty of celebrating. The singer took home five trophies at the 27th annual CMA Awards, including Entertainer of the Year, making Gill the night's biggest winner.

Along with Entertainer of the Year, Gill's awards during the evening included Male Vocalist of the Year, Vocal Event of the Year (as part of George Jones' "I Don't Need Your Rockin' Chair"), Album of the Year and Song of the Year. The Song of the Year honor was for "I Still Believe in You," which the singer also wrote.

Gill spent plenty of time onstage during the CMA Awards broadcast in 1993: In addition to taking home multiple awards, the Oklahoma native also co-hosted the ceremony with Clint Black. It was Gill's second year hosting the CMA Awards, and he went on to host the event 10 more years, making him the longest concurrent host in the history of the show.

Gill won seven more CMA Awards after 1993, including taking home Male Vocalist of the Year honors in 1994 and 1995. In his legendary career, which has spanned 35-plus years, he has won a total of 18 CMA Awards, as well as several ACM Awards and Grammys.

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