November 13, 2008 — The Country Music Association’s annual awards are designed to pay homage to best of the genre over the course of the previous year, and the CMA certainly did that with its 42nd presentation, though the event was bathed in subtle history.

Sugarland’s Jennifer Nettles was a double winner as the duo affirmed its rise to prominence in an area dominated for more than a decade by Brooks & Dunn. Lady Antebellum grabbed its first trophy from the organization, and several artists who earned their first Top 10 country hits in 2008 — Darius Rucker, James Otto and Kid Rock — performed during the three-hour telecast.

But that history was still present in wins by George Strait, Kenny Chesney and Rascal Flatts. George’s Troubadour claimed Album of the Year and "I Saw God Today" took Single, elevating his status as a country legend. As both artist and co-producer on those recordings, George walked away with four trophies, giving him a career total of 22. That makes him the top CMA winner of all-time, surpassing Brooks & Dunn’s 19.

Troubadour is doubly impressive given George’s longevity. It’s been 27 years since the cowboy scored his first hit, and he’s survived numerous trends and continued making quality music at a point in his career when most acts would be living off their fans’ nostalgia. In fact, Troubadour is his second straight release to win Album, following on the heels of It Just Comes Natural. Rather improbably, both awards come after he was already inducted into the Country Music Hall of Fame.

"Everybody says they got the greatest fans," George said during his second acceptance speech of the night. "Well, I’ve really got the greatest fans."

Among them is his producer, Tony Brown. Tony’s worked with tons of major acts — Reba McEntire, Vince Gill, Elvis Presley, Brooks & Dunn — and even he’s impressed with George’s continued mastery of his art.

"It’s amazing to work with an artist who is still so relevant who’s been around so long," Tony told reporters backstage.

George has managed a lengthy and consistent career in great part because of his belief in songs, and Kenny Chesney — who spent several years touring as an opening act on George’s stadium shows in the late 1990s — apparently learned those lessons.

Kenny tied a record by winning his fourth Entertainer of the Year award in the last five years. The only other act to claim Entertainer four times is Garth Brooks, and Kenny seems to have five in his sites.

"Come get me," he said backstage, offering a challenge to next year’s competition. "At some point — just ask Reba McEntire and ask George Strait and ask Garth and ask Alabama — sooner or later they’re gonna move on to something else, but to the other four acts that are nominated [in 2009], I’m not gonna lay down either."

Rascal Flatts tied the Statler Brothers in winning the Vocal Group award for the sixth year in a row. (The Statlers won nine over the course of their career, a mark that’s safe until at least 2011).

"You can’t dream that big," lead singer Gary LeVox said backstage.

Backstage, Flatts mentioned numerous acts — the Statlers, the Eagles, Restless Heart, Exile, Boyz II Men — all of which inspired their vocal harmony.

The weight of history was on other minds as well. Two-time winner Brad Paisley, who co-hosted for the first time, said after the show it was "amazing to think about who’s done this before." The hosting ranks include Vince Gill and Brooks & Dunn in recent years, and Roy Rogers & Dale Evans in more historic times.

In perhaps the ultimate acknowledgement of modern country’s ties to history, however, Lady Antebellum claimed New Artist of the Year, an award that’s gone previously to such acts as Garth Brooks, Randy Travis, Rascal Flatts and LeAnn Rimes.
All of those names "reminded me of how nostalgic this awards ceremony is," Lady A’s Hillary Davis noted backstage. "You think about how many people have stood here before you — [it’s] very humbling. We do not take this lightly at all."

Particularly Hillary, who has some history of her own. She attended previous CMA ceremonies with her mother, Linda Davis, who earned one trophy (though not on a night Hillary was in tow) for "Does He Love You," a duet with Reba McEntire.
"For her to have this crystal trophy on her shelf at home and me to be takin’ one home tonight," Hillary observed, "it’s crazy."