Born in Southgate, California, Sullivan and his family eventually found their way to Lubbock, Texas, where he met Holly as a teenager. Unbeknownst to them at the time, the two were actually third cousins. Sullivan stumbled into a musical partnership with Holly in late 1956, when a mutual friend took him along to Holly’s house to record the future legend with a hand-held tape deck. Upon learning that Sullivan played guitar, Holly asked him to retrieve his instrument from his car, and with drummer Jerry Allison they began working on songs.
Sullivan, who was delivering flowers for a living at the time, was with the band for the early 1957 sessions that yielded “That’ll Be the Day” and “I’m Looking for Someone to Love,” and was a regular part of Holly’s touring troupe at the time. Though Holly often went to outside vocalists for backing on his songs, Sullivan provided the additional voice on two of Holly’s bigger hits, “That’ll Be the Day” and “Not Fade Away.”
Despite being in on the group’s success (“That’ll Be the Day” topped the charts in August 1957), Sullivan’s tenure was short-lived. The guitarist claimed to never quite fit in with Holly, Allison and bassist Joe Mauldin, whose penchant for teasing and pranks while on the road never sat well with Sullivan. “We all did pick on each other,” Sullivan said in the Holly biography Remembering Buddy, “but it really grated on me. I took things more personal than the other guys did.”
Holly and the Crickets initially performed as a trio, eventually bringing guitarist Tommy Allsup on board. Holly left the Crickets in the fall of 1958; he was killed in a plane crash in February 1959.
Sullivan signed his own label deal after his departure and a single, “It’s All Over,” enjoyed some regional success. He then headed to Los Angeles where he joined Soul Incorporated before retiring as a performer and working for Sony Electronics.
Sullivan’s contribution to the group was not recognized in the 1978 biopic The Buddy Holly Story. Although he claimed to strike a deal that would have given him a percentage of “That’ll Be the Day” earnings, Sullivan maintained that the only money he was ever paid for his Crickets tenure was a weekly stipend while on tour in 1957, a small severance check shortly after his departure and royalties on “I’m Gonna Love You Too.”