

Throughout the 1990s and into the 2000s, the duo was no stranger to country music radio, racking up a total of twenty Number One hits and fifty chart singles overall. They were also a shoo-in for the Country Music Association's Duo of the Year award (winning it from 1992 through 2006), as well as an Entertainer of the Year award in 1996 after the smash cover of B. Stevenson's "My Maria", which was also the biggest country hit of that year.

The duo started to slip into more of a pop sound, maintaining the hits for the time being but losing its critical acclaim. Come 1999, the duo hit its first commercial low point, as the album Tight Rope produced only one big hit and disappointing sales. Montgomery Gentry who was only two singles into its career at that point got the 1999 Duo award at the Academy of Country Music. Only two years later, Brooks & Dunn got back on track, launching that year with "Ain't Nothing 'bout You", the biggest hit of the duo's career and the biggest country single of 2001. The hits kept on coming for the next few years, but following a second Greatest Hits album, they started to fade away again. Hillbilly Deluxe did account for the duo's last #1 hit in "Play Something Country" and the signature song "Believe", but Cowboy Town sold poorly (even if it produced three Top 10 hits). Kix also found work as a radio host, succeeding Bob Kingsley on the countdown show American Country Countdown in 2006.
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