The best songs that didn't make this Top 10 Kenny Chesney Songs list would be better than 95 percent of similar lists for other artists. With 21 No. 1 hits and a seven-year span in which the singer never left the Top 5, Chesney is arguably the top country artist of the last 20 years. Which song do you think should be the No. 1 Kenny Chesney song of all time?