I've listening to The Very Best Of Buddy Holly & The Crickets album from Universal Records, the nice double disc album was originally released in 1999, and contain all of Buddy Holly's hit singles (but does not contain his early 1956 singles, probably due to contractual reasons).
Charles "Buddy" Holley's rock and roll career actually didn't start until he saw Elvis Presley in concert in 1955, and decided to change his then bluegrass-style of music to more rockabilly. When his talent was noticed and eventually signing to Decca Records in 1956, he started using the name "Buddy Holly", thanks to a misspelling of his name on his contract to Decca.
This is where it went strange: Decca decided to not renew Holley's contract in 1957, but, his contract restricted Holly from actually recording songs for other labels for the next five years. Holly decided to record under his band The Crickets, and they signed with Brunswick Records. Meanwhile, as a solo artist, he signed Buddy Holly under Coral Records. Both labels were Decca subsidiary.
Being in the Crickets proved a big hit for Buddy Holly. In just a year, he produced the big hit single, "That'll Be The Day" billed under The Crickets. Meanwhile, because he was also signed as solo artist, he also released two hit singles under his own name: "Peggy Sue" and "Oh Boy!" (you all know that song, "all my love, all my kisses, you don't know what you've been missin', oh boy!").
Buddy Holly was at the height of his popularity in 1958 and 1959, so it was a terrible blow to music when he, along with Ritchie Valens and J. P. "The Big Bopper" Richardson, was killed in a plane crash to Moorhead, Minnesota.
The Very Best Of Buddy Holly & The Crickets track listing doesn't make any sense to me, it's definitely not chronological. Instead, whoever put together the list grouped the biggest hits early on disc one, although hit songs like "Everyday" is spaced near the end (if they were going to group hits, this song should be right next to "Peggy Sue", in my opinion).
Disc two is basically non-essential tracks, although oddly the "Peggy Sue" sequel song "Peggy Sue Got Married" is the lead track on disc two.
Listening to the fifty tracks, many of these songs sound similar, but you also have to realize how amazing it was that they've managed to produce all this music within a brief span of time (1957-1958). Most artists today are lucky to write a hit now and then, let alone twenty of them in a few years.
Anyway, this collection is really meant for both casual and collectors. The audio was remastered, so it sounds great. When you listen to Buddy Holly, you're often reminded how he help shaped rock and roll today.