The 10 Best Buddy Holly Songs of All Time

Buddy Holly was one of the pioneers in the rock-and-roll music industry. He came on the scene when the genre had found its way onto the airwaves and played at dances. Many parents during this conservative age had a problem with rock-and-roll music, but his music helped bridge the gap between the generations and open the doors for greater acceptance. Buddy Holly became a teen idol. He left the earth too soon, but his biggest hits remain. Here are the ten best Buddy Holly songs of all time as ranked from worst to best.

10. “It’s So Easy”

“It’s So Easy” is a song about falling in love. Most of us have at least heard it, even if we do not hail from the generation when Holly was a sensation. The song still receives play and covers in television ads and commercials. It’s a happy and fun song that you can’t help but tap your foot to.

9. “You’re So Square”

“You’re So Square” is an old classic song that gives us a good dose of the colloquialism of the era. The English language was a lot different in the 1950s. Being called a “square” isn’t a compliment. This song holds a lot of nostalgia and it’s still a favorite for ’50s fans.

8. “Maybe Baby”

“Maybe Baby” was a big hit for Buddy in 1957. The song charted high in the United States. It was even more popular in the United Kingdom. It’s an innocent song about longing for a love that will last, and finding the one that will be true. The simplicity of this song is reminiscent of wearing saddle shoes and a poodle skirt in more innocent times.

7. “Words of Love”

“Words of Love” is another easy-going song that Buddy put over nicely with his golden boyish voice. The big drawing card for this song was his guitar work. In the ’50s, hitting a few nifty riffs drove the audiences wild.

6. “Blue Days Black Nights”

Spinditty ranked this as the number one song from Buddy Holly, while it appeared as number four for The Good, The Bad, and The Unknown. Nearly seventy years later, we all have our preferences in classic fifties rock. It’s a subjective situation and we give this a six for its value in the evolution of rock and roll, when it began turning the corner as Holly did from a country flavor here. It’s a sad song, about realizing his behaviors could have been better. It gets a ranking in the middle.

5. “Think It Over”

“Think It Over” is a song about longing for a girl to change her mind about you. It’s an innocent song that makes us think about a girl who can’t make up her mind about a guy. She’s pretty sure that he’s not the one but he holds out the hope that she could change her mind when he tells her to think it over again.

4. “Oh Boy!”

“Oh Boy!” is one of the most enjoyable songs that Buddy Holly ever released. The song came out in 1957 and it reeks of innocent first love. Almost everyone knows the words and can sing along. “All my love, all my kissin’ You don’t know what you’ve been missin’ Oh Boy!” Every time I hear this song I have to smile. It’s been covered by a lot of bands since Holly’s death because it’s too good not to keep the song alive.

3. “That’ll Be The Day”

We listed “That’ll Be The Day” as the third best song of Buddy Holly’s short but phenomenal career. Return of Rock adds to the value of this song by sharing a bit of trivia about its origins. They contributed that Holly wrote the song after he watched the John Wayne film “The Searchers.” He turned the iconic phrase that the Duke repeated throughout the film, into a title for one of the greatest songs ever. Somehow, this story makes it all the better. It somewhat changes my perception of the song in a positive way. I didn’t realize that Buddy Holly was a John Wayne fan. It’s all good.

2. “Peggy Sue”

This is one of Buddy Holly’s most iconic songs. He’s best known for “Peggy Sue,” the tune that he wrote with Norman Petty. It’s a song that charted the year of its release in 1957, and it made it to number three. The song was one of his biggest hits and it still puts us in mind of a more innocent and simple time in the history of the country. Buddy Holly was able to show off a bit of his creativity and versatility when he sang “Peggy Sue.” It is a fun song that will never fade in its popularity. It will forever be linked with the iconic Buddy Holly.

1. “Everyday”

“Everyday” is a light song that can take you away from your thoughts and immerse you in a mellow and positive mood. It’s my favorite Buddy Holly song of all time. Holly sang it so smoothly and easily. It’s about life and love and the endless possibilities that every new day can bring. “Everyday” is a song that has been covered by various artists. This includes James Taylor and Don McLean, among other notable modern artists. The simplicity of the song can carry you away as though on a gentle summer breeze. It’s that good.

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