His first known recording was created in 1949 when Buddy made a recording of Hank Snow's 'My Two-Timin' Woman' on a wire recorder "borrowed" by a friend who worked in a music shop (not, as is often reported, a home tape recorder). During the fall of that year he met Bob Montgomery in Hutchinson Junior High School. They shared a common interest in music and soon teamed up as the duo "Buddy and Bob." Initially influenced by bluegrass music, they sang harmony duets at local clubs and high school talent shows. His musical interests grew throughout high school while singing in the Lubbock High School Choir.
Holly turned to rock music after seeing Elvis Presley sing live in Lubbock in early 1955. A few months later, he appeared on the same bill with Presley, also in Lubbock. Holly's transition to rock continued when he opened for Bill Haley & His Comets at a local rock show organized by Eddie Crandall, who was also the manager for Marty Robbins. As a result of this performance, Holly was offered a contract with Decca Records to work alone, which he accepted. It’s reported that his public name changed from "Holley" to "Holly" on 8 February 1956, when he signed the Decca contract. Among the tracks recorded for Decca was an early version of "That'll Be The Day", which took its title from a phrase that John Wayne's character said repeatedly in the 1956 film, The Searcher.
Back in Lubbock, Holly formed his own band, although at that time it had no name and would only later be called The Crickets. The band began recording at Norman Petty's studios in Clovis, New Mexico. Norman had music industry contacts and believing that "That'll Be the Day" would be a hit single, he contacted publishers and labels. Coral Records, a subsidiary of Decca, signed The Crickets. Soon after, they signed Holly as a solo artist. This put Holly in the unusual position of having two record contracts at the same time.
The ambitious Holly became increasingly interested in the New York music/recording/publishing scene, while his younger and more easygoing bandmates wanted to go back home to Lubbock. As a result, in 1959 the group split.
Holly began a solo tour with other notable performers, including Dion and the Belmonts, Ritchie Valens, and J.P. "The Big Bopper" Richardson. After a performance in Green Bay, Wisconsin at the Riverside Ballroom, on 1 February the tour moved on to the Surf Ballroom in Clear Lake, Iowa on 2 February 1959. Afterwards, Buddy Holly chartered a Beechcraft Bonanza to take him and his new back-up band (Tommy Allsup and Waylon Jennings) to Fargo, North Dakota, enroute to play the next leg of the Winter Dance Party tour at the Armory in Moorhead, Minnesota. Carl Bunch missed the flight as he had been hospitalized with frostbite three days earlier. The Big Bopper asked Jennings for his spot on the four-seat plane, as he was recovering from the flu. Ritchie Valens was still signing autographs at the concert site when Allsup walked in and told him it was time to go. Valens begged for a seat on the plane. Allsup pulled a 50 cent coin out of his pocket and the two men flipped for the seat. Allsup lost.
The plane took off in light snow and gusty winds at around 12:05 A.M., but crashed a few minutes later. The wreckage was discovered several hours later by the plane's owner, Jerry Dwyer, some 8 miles from the airport on the property of Albert Juhl. Although the crash received a good deal of local coverage, it was displaced in the national news by an accident that occurred the same day in New York City, when American Airlines Flight 320 crashed during an instrument landing approach at LaGuardia Airport, killing 65. Don McLean referred to it as "The Day the Music Died".
We've got a couple of his hits in the Jukebox. Feel free to punch them up and listen.