Holly's recording sessions at Decca were produced by Owen Bradley, who had become famous for producing orchestrated country hits for stars like Patsy Cline. Unhappy with Bradley's musical style and control in the studio, Holly went to producer Norman Petty in Clovis, New Mexico, and recorded a demo of "That'll Be the Day", among other songs. Petty became the band's manager and sent the demo to Brunswick Records, which released it as a single credited to "The Crickets", which became the name of Holly's band. In September 1957, as the band toured, "That'll Be the Day" topped the US and UK singles charts. Its success was followed in October by another major hit, "Peggy Sue".

The album Chirping Crickets, released in November 1957, reached number five on the UK Albums Chart. Holly made his second appearance on The Ed Sullivan Show in January 1958 and soon after, toured Australia and then the UK. In early 1959, he assembled a new band, consisting of future country music star Waylon Jennings (bass), famed session musician Tommy Allsup (guitar), and Carl Bunch (drums), and embarked on a tour of the midwestern U.S. After a show in Clear Lake, Iowa, he chartered an airplane to travel to his next show, in Moorhead, Minnesota. Soon after takeoff, the plane crashed, killing Holly, Ritchie Valens, The Big Bopper, and pilot Roger Peterson in a tragedy later referred to by Don McLean as "The Day the Music Died".

During his short career, Holly wrote and recorded several songs. He is often regarded as the artist who defined the traditional rock-and-roll lineup of two guitars, bass, and drums. He was a major influence on later popular music artists, including Elvis Presley, Bob Dylan, The Beatles, The Rolling Stones, Eric Clapton, The Hollies (who named themselves in his honor), Elvis Costello, Marshall Crenshaw (who later played Holly), and Elton John. He was among the first artists inducted into the Rock and Roll Hall of Fame, in 1986. Rolling Stone magazine ranked him number 13 in its list of "100 Greatest Artists".

By 1955, after graduating from Lubbock High School, Holley decided to pursue a full-time career in music. He was further encouraged after seeing Elvis Presley performing live in Lubbock, whose act was booked by Pappy Dave Stone of KDAV. In February, Holley opened for Presley at the Fair Park Coliseum, in April at the Cotton Club, and again in June at the Coliseum. By that time, he had incorporated into his band Larry Welborn on the stand-up bass and Allison on drums, as his style shifted from C&W to rock and roll due to seeing Presley's performances and hearing his music. In October, Stone booked Bill Haley & His Comets and placed Holley as the opening act to be seen by Nashville scout Eddie Crandall. Impressed, Crandall persuaded Grand Ole Opry manager Jim Denny to seek a recording contract for Holley. Stone sent a demo tape, which Denny forwarded to Paul Cohen, who signed the band to Decca Records in February 1956. In the contract, Decca misspelled Holley's surname as "Holly", and from then on he was known as "Buddy Holly".

On January 26, 1956, Holly attended his first formal recording session, which was produced by Owen Bradley. He attended two more sessions in Nashville, but with the producer selecting the session musicians and arrangements, Holly became increasingly frustrated by his lack of creative control.  In April 1956, Decca released "Blue Days, Black Nights" as a single, with "Love Me" on the B-side. Denny included Holly on a tour as the opening act for Faron Young. During the tour, they were promoted as "Buddy Holly and the Two Tones", while later Decca called them "Buddy Holly and the Three Tunes".  The label later released Holly's second single "Modern Don Juan", backed with "You Are My One Desire". Neither single made an impression. On January 22, 1957, Decca informed Holly his contract would not be renewed, but insisted he could not record the same songs for anyone else for five years.

Holly was unhappy with the results of his time with Decca; he was inspired by the success of Buddy Knox's "Party Doll" and Jimmy Bowen's "I'm Stickin' with You", and visited Norman Petty, who had produced and promoted both records. Together with Allison, bassist Joe B. Mauldin, and rhythm guitarist Niki Sullivan, he went to Petty's studio in Clovis, New Mexico. The group recorded a demo of "That'll Be the Day", a song they had previously recorded in Nashville. Now playing lead guitar, Holly achieved the sound he desired. Petty became his manager and sent the record to Brunswick Records in New York City. Holly, still under contract with Decca, could not release the record under his name, so a band name was used; Allison proposed the name "Crickets". Brunswick gave Holly a basic agreement to release "That'll Be the Day", leaving him with both artistic control and financial responsibility for future recordings.

Impressed with the demo, the label's executives released it without recording a new version. "I'm Looking for Someone to Love" was the B-side; the single was credited to the Crickets. Petty and Holly later learned that Brunswick was a subsidiary of Decca, which legally cleared future recordings under the name Buddy Holly. Recordings credited to the Crickets would be released on Brunswick, while the recordings under Holly's name were released on another subsidiary label, Coral Records. Holly concurrently held a recording contract with both labels. Full article