Buddy Holly’s 10 Best Songs

Updated on April 23, 2020
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I've been an online writer for over seven years. I love history, books, and television. There is always something new to discover.

Buddy Holly died at the start of his career. He was on the Winter Dancy Party Tour along with other great performers of the 1950s, including The Big Bopper and Ritchie Valens. The tour wasn’t planned very well. The venues were spaced far apart. The group had to ride in unheated tour buses, it was February and the weather in the Midwest can be very cold that time of year. After spending a few nights on the cold bus, Buddy decided to charter a plane. That decision cost him his life. Buddy, Ritchie, The Big Bopper, and the pilot lost their lives. One wonders how many things Buddy would have accomplished had he lived. He was just twenty-two at the time of his death, yet he was already seeing great success as a performer, songwriter, and producer.

Buddy was listed as number 13 on Rolling Stone magazine's list of the 100 Greatest Artists. It is easy to understand why. Without Buddy, there would be no Beatles, no Rolling Stones, no Elton John, and no Bob Dylan. They are just a few of the musicians who were inspired by Buddy Holly.

Listening to his songs, they're always guaranteed to make you feel uplifted and entertained. Buddy Holly had so many great songs during his career, but these are the songs that stand out the most.

Buddy Holly’s Best Songs

  1. “Blue Days, Black Nights”
  2. “Think It Over”
  3. "Everyday"
  4. “That'll Be The Day”
  5. "Oh Boy"
  6. "Maybe Baby"
  7. "It's So Easy"
  8. "Listen to Me"
  9. "Words of Love"
  10. "Peggy Sue"

1. “Blue Days, Black Nights”

Album: That'll Be the Day

Release Year: 1958

During his childhood, Buddy Holly was inspired by country music and the blues. This song has that country sound. The song begins with an excellent guitar riff, then Buddy starts in with his strong lyrics. While the guitars build a wall of sound, Buddy pours his heart out, singing of a love he regrets having treated badly. The lyrics at the end say it best.

Blue days, black nights, I didn’t realize

I would miss you, the way I do

And now somehow, I know I will pay

For the times I have made you blue

Memories of you make me sorry

I gave you reason to doubt me

But now you’ve gone, and I am left here all alone

With blue memories, I think of you

— Buddy Holly, "Blue Days, Black Nights"

2. “Think It Over”

Album: The Buddy Holly Story

Release Year: 1958

This song rocks and Buddy sings with a swagger. It is a song that you can picture the kids dancing down the line to on American Bandstand. The song has a surprise piano riff that comes in near the end. It's an incredible piece of music.

Think it over what you just said

Think it over in your pretty little head

Are you sure that I'm not the one

Is your love real or only fun

— Buddy Holly, "Think It Over"

3. "Everyday"

Album: Buddy Holly

Release Year: 1958

This adorable song was written by Buddy Holly and Norm Petty. In the days of 45 rpms, you would get a side A and a side B. When this 45 came out, side A contained the song “Peggy Sue” and side B contained the song “Everyday.” Whoever bought that record got quite a deal! Both songs are spectacular.

To this day, the song “Everyday” has been featured in movies and tv shows. It is easy to see why. The song has a sweet child-like sound to it. It sounds like an ice cream truck is on its way. The instrumentation is so simple, yet so perfect. Jerry Allison slaps his knee and uses a typewriter, Buddy plays an acoustic guitar, Joe B. Mauldin plays a stand-up bass, and Norm Petty’s wife Vi plays a celesta, which sounds a lot like a glockenspiel. It gives the song a German sound.

It is a song that was never released as a single by Buddy. Years later, John Denver recorded the song, and so did James Taylor. The song sounds so innocent. The singer hopes that the girl he likes will soon be his and that love will be theirs forever.

Everyday, it's a gettin' closer,

Goin' faster than a roller coaster,

Love like yours will surely come my way, (hey, hey, hey)

Everyday, it's a gettin' faster,

Everyone says go ahead and ask her,

Love like yours will surely come my way, (hey, hey, hey)

— Buddy Holly, "Everyday"

4. “That'll Be the Day”

Album: The "Chirping" Crickets

Release Year: 1957

This song was released in May of 1957 and it went to number 1 in the United States and the U.K. It is a song that was inspired by a movie starring John Wayne. Buddy and Jerry went to the movies one night to see the western movie The Searchers. In the movie, whenever John Wayne’s character heard something he didn’t agree with, he would say, “That’ll Be The Day.” One night, Jerry and Buddy were hanging out at Jerry’s house and Buddy said, “It sure would be nice if we could record a hit song.” To which Jerry replied, “That’ll Be The Day.” Suddenly, that short conversation inspired one of Buddy's greatest songs.

It's funny to think that Buddy and Jerry were inspired to write “That’ll Be The Day" by a movie, and that their song would later inspire John Lennon. (It was the first song he learned to play on his guitar.)

It's amazing how this song still sounds fresh. The song begins with a great guitar lick, and then Buddy sings with powerful assurance.

Well, that'll be the day, when you say goodbye

Yes, that'll be the day, when you make me cry

You say you're gonna leave, you know it's a lie

'Cause that'll be the day when I die

— Buddy Holly, "That'll Be the Day"

5. "Oh Boy"

Album: The Chirping Crickets

Release Year: 1957

The single reached number 10 in the United States and number 3 in the U.K. There was an interesting story to the song. The song was performed on the group’s second appearance on The Ed Sullivan Show January 26, 1958. Ed didn’t want the group to perform that song because he thought the lyrics were raunchy. The group did it anyway and Buddy was trying to turn up the volume on his guitar, which had been set to low. Another article goes into more detail. Ed came in the dressing room and asked that Buddy and the group change the song because of it being raunchy. Buddy said that he had told his hometown friends that was the song he was going to sing and he wasn’t going to change his mind.

Ed Sullivan requested the group do a last-minute rehearsal. And, when Ed went to the dressing room, only Buddy was there. Ed said, “Well I guess The Crickets are not too excited to be on The Ed Sullivan Show." Buddy responded by saying, “I hope they’re damned more excited than I am.” Ed, of course, got angry at that. He got back at them by only allowing them to perform one song, instead of the usual two. He also mispronounced Buddy’s name as "Buddy Hollet." The Crickets were a big hit, and Ed tried to get them to return to the show. Buddy wasn’t having it and said Sullivan didn’t have enough money for that.

Buddy sings the song with swagger. Buddy knew what he wanted, and he conveyed his personality through this song. It is a great, rockin' song.

All of my love

All of my kissin'

You don't know what you've been a-missin'

Oh boy, when you're with me

Oh boy, the world can see

That you, were meant, for me

— Buddy Holly, "Oh Boy"

6. "Maybe Baby"

Album: The "Chirping" Crickets

Release Year: 1957

The song was released in 1957. It reached number 17 in the United States and number 4 in the U.K. The song is very catchy. It moves like a boat through the water, very smooth. The background vocals and ringing guitar bring the song to life. It is a song of confidence and hope for a long-lasting love. The lyrics really bring it home.

Maybe baby, I'll have you

Maybe baby, you'll be true

Maybe baby, I'll have you for me (all for me)

It's funny honey, you don't care

You never listen, to my prayer

Maybe baby, you will love me some day (someday)

— Buddy Holly, "Maybe Baby"

I love the part of the song where the background singers sing:

"Da-da-ta-da-da-da da-da-da
Da-da-ta-da-da-da da-da-da
Da-da-ta-da-da-da da-da-da

Those lyrics just take the song and make it fly higher.

7. "It's So Easy"

Album: The "Chirping" Crickets

Release Year: 1957

This song was the last one released by The Crickets while Buddy was still in the band. But, for some weird reason, it didn’t chart. Linda Ronstadt had better luck with the song. She released her cover version in 1977 and it got to number 5 on the U.S. charts. Maybe the song was just ahead of its time.

The song is lively and has great guitar picking going on throughout. Buddy truly sings his heart out on this one. His band is right behind him, giving the song even more lift. Buddy usually played lead guitar. But, for this song, Tommy Allsup took the reins and did a great job.

It's so easy to fall in love.

It's so easy to fall in love.

People tell me love's for fools.

So, here I go, breaking all the rules

— Buddy Holly, "It's So Easy"

8. "Listen to Me"

Album: Listen to Me: Buddy Holly

Release Year: 2011

This song was never released as a single, but it should have been. The song is played and sung softly with Buddy using all his powers of persuasion. The drums play along with Buddy and then the guitar goes into a beautiful riff. The middle of the song really comes alive with Buddy repeating "Listen, listen to me." All the while, the guitar riff continues beautifully and the drums play softly along. It's at that point that you will think Buddy will win the girl over by the end of the song. It is a haunting love song.

Your eyes will see what love can do

Reveal to me your love so true

Listen to me, listen closely to me

I've told the stars you're my only love

I want to love you to tenderly

Those same bright stars in heaven above

Know now how sweet sweethearts can be

— Buddy Holly, "Listen to Me"

9. "Words of Love"

Album: Buddy Holly

Release Year: 1957

This song was released in 1957, but it wasn’t much of a hit for Buddy. He wrote the song himself and he harmonized with himself by doing tape dubs. The song sounds a little like “Listen to Me,” but that's ok, because that song is also great. Buddy sings the song in a loving manner. His brilliant guitar riff really holds the song together. It is the best part of the song. In fact, in the middle of the song, the guitar is brought to the forefront to draw more attention to it. It is truly wonderful. Buddy sings the song well. “Words of Love” should have charted. It is a song that every fan knows.

Hold me close and tell me how you feel

Tell me love is real

— Buddy Holly, "Words of Love"

10. "Peggy Sue"

Album: Buddy Holly

Release Year: 1957

This song was written by band member Jerry Allison and Norman Petty. The song was originally entitled, “Cindy Lou” after Buddy’s niece, but Jerry begged Buddy to change the song to Peggy Sue. His girlfriend was named Peggy Sue and, Jerry thought this song would get them back together because they were broken up at the time. It worked! Not only did they get back together, they ended up getting married.

The song was released in the early days of rock and roll, but the techniques that Norman used in the song are amazing. The drum beats that Jerry laid out had an echo sound that faded in and out. It really made the song stand out.

“Peggy Sue” made it to number 3 on the United States charts and it's surprising that it couldn’t make it to number 1. The song is pure magic. Buddy sings it with such feeling. The guitar, bass and drums go at a fast pace, then, when we get to the middle, the song really comes alive. The drums get louder and the guitar chimes out. It is a song you can’t help singing along with. This must be Buddy’s best song. The vocals, the instruments, and the production techniques make it unforgettable.

Buddy Holly was influenced by Hank Snow, a country singer, Elvis Presley, Bill Hailey and the Comets, and Bo Diddley. If we didn’t have Buddy Holly, we wouldn’t have some of the best performers in rock. Buddy influenced The Beatles, The Rolling Stones, Bob Dylan, Elvis Costello, Elton John, and so many others. In the song “American Pie,” Don McClean has lyrics that say:

But February made me shiver,

With every paper I'd deliver,

Bad news on the doorstep,

I couldn't walk one more step

I can't remember if I cried,

When I read about his widowed bride,

But something touched me deep inside,

The day the music died

— Don McClean, "American Pie"

In these lyrics he is referring to the day when Buddy Holly, The Big Bopper, and Ritchie Valens died in a plane crash. Luckily, the music didn't actually die. It lived on, and it grew. Buddy provided a template for performers to come. He also left the world with songs that are inspiring and make you feel happy just to hear them. He was a very talented man. He created songs that will give the listener joy for years to come.


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