Remember When Carrie Underwood Won Her First Entertainer of the Year Award?

Underwood went up against Brad Paisley, Kenny Chesney, Keith Urban and George Strait for the prestigious trophy.

Written by Lauren Laffer
Remember When Carrie Underwood Won Her First Entertainer of the Year Award?
Carrie Underwood

The 52nd Annual Academy of Country Music Awards are only a few days away and we’re getting ourselves ready by looking back at one of our favorite ACM moments: Matthew McConaughey presenting Carrie Underwood with the 2009 Entertainer of the Year award.

“1987, my brother and I left Longview, Texas and took a short road trip to the oil palace in Tyler, Texas to see this new hot artist by the name of Dwight Yoakam, and while we’re there we meet a couple of ladies that we’re trying to pick up,” the actor said to the crowd. “Conversation comes around to what we do for a living and on cue my brother and I said well, we have an exclusive contract with George Strait, we custom make his boots… The point of the story is, we got lucky that night. Thank you George.”

After a good laugh from the crowd, it was time for the most suspenseful moment of the night. Underwood went up against Brad Paisley, Kenny Chesney, Keith Urban and Strait himself for the prestigious trophy. Being just in the same category as those country stars was an honor in itself, but when her name was called to claim her prize she looked absolutely shocked.

“I’ve had a lot of good moments in the past four years, this one takes the cake,” the superstar said while trying to hold back the tears. “Thank you to the ACMs for nominating me in the first place, I never thought I’d be nominated and I never thought I’d win.”

Underwood was more than deserving of the 2009 award. In the year leading up to the show, the singer had four chart topping singles from her RIAA certified platinum album Carnival Ride, as well as a headlining tour of the same name.

“I don’t know what to say, I got nothing,” she wrapped up her speech. “I want to see those boots, Matthew.”

The “Dirty Laundry” singer has a chance to take home another Entertainer of the Year trophy this Sunday at the ACMs, which broadcast live from Las Vegas at 8 PM EST on CBS.