Bentley's studio albums have accounted for 25 singles on the Hot Country Songs and Country Airplay charts, of which 17 have reached number one: his debut single "What Was I Thinkin'", "Come a Little Closer", "Settle for a Slowdown", "Every Mile a Memory", "Free and Easy (Down the Road I Go)", "Feel That Fire", "Sideways", "Am I the Only One", "Home", "5-1-5-0", "I Hold On", "Drunk on a Plane", "Say You Do", "Somewhere on a Beach", "Different for Girls", "Woman, Amen" and "Living". Seven more of his singles have reached the top 5.