The Top 10 Buddy Holly Songs

For fans of Weezer, the name “Buddy Holly” is especially familiar.

Holly is also well known amongst music listeners who enjoy rock and roll songs from the 1950s. Truly, Holly is something of a legend in popular music. With his horn-rimmed glasses, skillful pop hits and that memorable name, the artist is synonymous with a formative era of rock today.

Beyond lore and legend, however, who was Holly, exactly? Where did he come from and what did he leave behind?

Well, famously, Holly (born Charles Hardin Holley) was amongst those early rock legends who died in a plane crash on February 3, 1959. He was just 22 years old. Following a show in Iowa, Holly chartered a plane to take him to his next gig in Minnesota. But soon after takeoff, the plane crashed. It killed Holly, along with music legends Ritchie Valens, The Big Bopper, and the pilot Roger Peterson. Songwriter Don McLean called it “the day the music died.”

Born in Lubbock, Texas, Holly learned to play guitar as a kid. He learned gospel, country, and R&B. He made his first local TV appearance in 1952. In 1955, he opened for Elvis and knew then music would be his passion.

His first early hit was the track, “That’ll Be The Day,” a song credited to The Crickets, which was Holly’s band. Today, Holly is thought of as a pioneer in rock, often credited as the one who popularized the rock lineup of two guitars, bass, and drums. He remains a great influence on rock and rockabilly.

For someone who could have rivaled the biggest stars, his death at 22 was a big loss. Nevertheless, let’s dive into the songs Holly left us. To that end, below are Buddy Holly’s Top 10 songs.

1. “That’ll Be The Day”

Written by Holly and drummer Jerry Allison, the track was first recorded by Holly and the Three Tunes in 1956. It was later re-recorded the following year by his new group, the Crickets. In 1957, the song became a national hit, Holly’s first.

2. “Everyday”

One of the best and most recognizable songs in rock music history, this track was released on September 20, 1957, as the B-side to “Peggy Sue” (see below). Since then, it’s earned a spot on the greatest American songs of all time. With rising and falling vocals and pitter-patter percussion, it’s like the platonic ideal of a 1950s pop hit.

3. “It Doesn’t Matter Anymore”

Written by legendary songwriter Paul Anka, and recorded by Holly in 1958, the song was released in 1959, a mere few weeks before Holly died. The song, which features orchestral background, hit No. 13 posthumously. It was Holly’s last U.S. Top 20 hit.

4. “Love Me”

“Love Me” sounds like it was written and performed by Elvis Presley, but, no, it’s Buddy Holly through and through. One can see his influence on early Beatles’ work from Paul and John, too. The track itself, which combines R&B, country, and pop, was released in 1956, the result of Holly’s first recording session at Bradley’s Barn in Nashville. “Love Me” was a commercial failure then, but a hit now.

5. “Send Me Some Lovin’”

A rock and roll standard first recorded by Little Richard and written by Leo Price and John S. Marascalso, “Send Me Some Lovin’” was recorded by Holly for the sole Crickets album, The “Chirping” Crickets. The record was released in the United States in 1957 and the United Kingdom a year later in 1958.

6. “Not Fade Away”

A prototypical early rock song, “Not Fade Away” was written by Holly and recorded by the Crickets. It was first recorded in New Mexico on May 27, 1957, the same day as “Everyday.” The song takes from a Bo Diddley beat.

7. “Rave On!”

Written by Sonny West, Bill Tilghman, and Norman Petty in 1958, the song was later recorded by Holly. His version became a hit single, one of six tracks that charted in 1958. In the song, he helped to popularize the elongated “Well,” which later became a signature to other rockers of the era, including Elvis.

8. “Peggy Sue”

Another of Holly’s most recognizable songs, “Peggy Sue” was written by drummer Jerry Allison and producer Norman Petty. Holly released it in 1957. The song was later re-released on his eponymous solo album in 1958. It features a constant guitar strum with some intermittent electric guitar exuberance. The song is about a love interest, “Peggy Sue.” For a follow-up, fans can check out the rockabilly “Peggy Sue Got Married,” too.

9. “Crying, Waiting, Hoping”

A song written by Holly, the track was released in 1959 as the B-side to the “Peggy Sue Got Married.” Over time, three versions of this song were released, including the 1959 version, a 1964 version with different orchestration, and Holly’s original private home recording. The song features early electric guitar soloing that’s especially skillful.

10. “Maybe Baby”

An earworm of a song, “Maybe Baby” was written by Holly and released by him and the Crickets in 1958. It was a top-40 hit in the U.S., U.K., and Canada.

Photo by Steve Oroz/Michael Ochs Archives/Getty Images