Singer Simon is a term that refers to three different singers: Paul Simon (4 letters), CARLY Simon (5 letters), and Estes Simon (5 letters). Paul Simon is an American singer-songwriter, musician, and actor who has been performing since the 1960s. He is best known for his work with Art Garfunkel in the duo Simon & Garfunkel. CARLY Simon is an American singer-songwriter, musician, and children's author who has been active since the 1970s. She is best known for her hit single 'YOU're So Vain'. Estes Simon is an American singer-songwriter and producer who has been active since the 1990s. He is best known for his work with hip hop artists such as Jay-Z and Kanye West.