Greatest Hits II is a compilation album by American country music artist Kenny Chesney. It was released on May 19, 2009, and it is his second greatest hits album since Greatest Hits in 2000. The album includes twelve singles from 2002 to 2009, as well as two non-singles from previous albums. Also included is the new song "Out Last Night", which was issued as a single in April 2009, followed by "I'm Alive" in August 2009.

Kenneth Arnold Chesney is an American country singer. He has recorded more than 20 albums that include more than 40 Top 10 singles on the U.S. Billboard Hot Country Songs and Country Airplay charts, 32 of which have reached number one. Many of these also have charted within the Top 40 of the U.S. Billboard Hot 100, making him one of the most successful crossover country artists. He has sold over 30 million albums worldwide.