A native of Washington, D.C., Greg Gaskins was raised in Northwest (NW) near the U St. area and its lively commercial and entertainment businesses. He began playing professionally as a guitarist when he was just 16 years old. He joined the noted D.C. band The El Corols in the late 1950s, frequently performing as the house band at Carr's Beach in Annapolis, Maryland. With the El Corols, he backed national artists including Patti LaBelle and the Bluebelles, Dionne Warwick, Martha Reeves and the Vandellas. He later performed in Billy Stewart's band at the Howard Theater and other venues. While working with Stewart at the Howard Theater, Greg had a fortunate encounter with The Manhattans; they hired him as their guitarist and he spent three years touring with them.
As a result of his work with The Manhattans, Greg was recruited by John Houston to accompany The Sweet Inspirations, a noted female vocal group who provided backing vocals for artists such as Wilson Pickett, Aretha Franklin, and Solomon Burke. (John Houston served as manager for The Sweet Inspirations, which included his wife Emily "Cissy" Houston, mother of Whitney Houston). Greg was a member of their band in 1969 when they toured, opened for, and served as background vocalists for Elvis Presley. Greg served as band director for The Sweet Inspirations and made a cameo appearance in the 1972 film "Elvis on Tour". He toured with The Sweet Inspirations and Presley through 1974. Over the course of his career, Greg also performed with Otis Redding, Jackie Wilson, Dee Dee Warwick, Al Green, Regina Belle, and The Five Stairsteps.