Prior to getting involved in the recording business, Niki Sullivan briefly served in the United States Navy. During the summer of 1956, the 19-year old Sullivan first met Buddy Holly, by way of his high school friend Jerry Allison, at a jam session in Lubbock, Texas. Holly was impressed by his guitar-playing talents and offered him the chance to join both of them, as well as Joe B. Mauldin in a band. Sullivan readily accepted the offer, and thus the Crickets were born.

While trying to record Peggy Sue after many disatisfying takes, Sullivan flipped a switch on Buddy's guitar, allowing him to break into the now-famous guitar solo. He also helped sing on back up and arrange the music to Not Fade Away (which he helped write), I'm Gonna Love You Too, That'll Be the Day, and Maybe Baby. It was around this period that he also wrote and produced the single "Look to the Future," which was recorded by Gary Tollett and The Picks, who often did back-up vocals for the Crickets.

Since he had a slight resemblance to Holly in his skinny posture and spectacles, he was often called "the other guy in glasses" by critics in their reviews. Coincidentally, he and Buddy were related third cousins, but it is not known whether they knew this or not. After their famous December 1, 1957 appearance on The Ed Sullivan Show, the group briefly went on hiatus to plan their next recordings. In early 1958, Sullivan formally announced that he had left the band for good. Exactly why he chose to do so remains in debate today. According to his memoir about life with Buddy titled Rave On, he admits that he was not very comfortable with the amount of touring, and he felt that he did not fit in with Jerry and Joe. Since Buddy sang and played lead guitar, Sullivan was left without much of a role in the group.

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