In 2000, McGraw released his Greatest Hits album, which topped the charts for nine weeks and sold almost 6 million copies, making it one of the biggest-selling albums in the modern country market. In the latter half of the year, he and Hill went out on the Soul2Soul Tour, playing to sellout crowds in 64 venues, including Madison Square Garden. It was one of the top tours of any genre in the US, and the leading country tour during 2000.
While in Buffalo, New York, McGraw and Kenny Chesney became involved in a scuffle with police officers after Chesney attempted to ride a police horse. McGraw came to Chesney's aid after police officers nearby believed the horse was being stolen and tried to arrest him. The two were arrested and charged with assault, but were later cleared. During a concert with the George Strait Country Music Festival several weeks later, Hill, dressed as a police officer, made an unscheduled appearance at the end of McGraw's set and led him off the stage.