Answer
James Taylor has topped the Billboard Hot 100 chart twice, with his songs "Fire and Rain" and "How Sweet It Is (To Be Loved by You)." "Fire and Rain" was released in 1970 and reached number one on the chart on April 26, 1970. "How Sweet It Is (To Be Loved by You)" was released in 1976 and reached number one on the chart on February 27, 1976.