2000 (tie): ‘Breathe’ by Faith Hill, ‘How Do You Like Me Now?!’ by Toby Keith, ‘I Hope You Dance’ by Lee Ann Womack and Sons of the Desert

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Number of weeks spent as #1: 5

Country-pop superstar Faith Hill continued her chart-topping dominance with “Breathe,” a five-week success story on the Hot Country charts. The song also spent a full year on the Hot 100 chart, making it Billboard’s top single of the year—an honor no other country song has earned in this century. Toby Keith also found crossover success with “How Do You Like Me Now?!” on the Hot 100 (it peaked at #31), while Lee Ann Womack hit #1 on both the Hot Country and Adult Contemporary charts, climbing to #14 on the Hot 100.