This picture was part of a video that won the Video of the Year award at the 2005 CMAs. The show took place in New York City that year -- at Madison Square Garden -- in an effort to broaden country music's reach. It was the first Video of the Year award for this artist, although he'd earn more in the future.

That pretty face in the picture is part of a twin billing that tries to seduce the singer out of the high-class martini bar he's sipping beer in. After popping a Viagra he agrees, but isn't too pleased when she turns to reveal her right side. One gets the feeling the myster star agrees to move ahead with the plan anyway, just for the fun of it. Do you think you know which music video this picture is from?