The term 'My Cup Runneth Over Singer' refers to the American singer-songwriter, Jim Ed AMES. He is best known for his hit single 'My Cup Runneth Over', which was released in 1967 and reached number 8 on the Billboard Hot 100 chart. The crossword solutions for this term are EDAMES (6 letters) and AMES (4 letters). These are both variations of his last name, which is a combination of his first name, Jim, and his middle name, Ed.