That’ll Be The Day: Our Pick of the 11 Best Buddy Holly Songs

Rock icon Buddy Holly was a driving force like no other in the 1950s. His unmatched vocal style, a mixture of techniques referred to as “hiccups” and “stutters,” captured listeners attention. Along with his signature Fender Stratocaster, he effortlessly blended country, blues, R&B, and pop genres together to create a fresh sound that would go on to influence everyone from The Rolling Stones and The Beatles to contemporary pop-rock band Weezer.

In his late teens and early twenties, he released a string of hits. At just twenty years old, he and his band The Crickets scored their first and (surprisingly) only number 1 hit, ‘That’ll Be The Day.’ In the prime of his career, Holly and fellow musicians Ritchie Valens and the Big Bopper tragically died in a small plane crash. Songwriter Don McLean would go on to recognize this tragic event as “the day the music died” with his hit ‘American Pie.”

Buddy Holly and The Crickets represent a form of rock music that is both innovative and timeless. Check out our pick of the best Buddy Holly songs below.

11. Not Fade Away

All of Buddy Holly’s biggest hits are included on our list, but we couldn’t leave one of rock’s most defining songs off of this countdown, even though it wasn’t super popular among Crickets fans at the time of its release. Included on the B-side of a record, ‘Not Fade Away’ wasn’t a huge hit, but its masterful production and visionary songwriting make it legendary among rock music crowds. As one of rock’s early trailblazers, Holly’s sound was not only unique to the genre, but it was unlike anything people had heard before no matter what you listened to. Buddy brilliantly blends his dynamic falsetto and full voice with his ‘Not Fade Away’ performance while utilizing a beat that hadn’t been commercialized yet, the “Bo Diddley Beat.” Featuring a syncopated guitar and drum rhythm with powerful stops both during vocal lines and in between lyrics, this sound, originally brought to people’s attention by R&B musician Bo Diddley’s ingenuity, would go on to be used in countless rock and pop tunes. During rock’s infancy, ‘Not Fade Away’ was a defining moment for the genre, and shaped its direction for generations to come.

Recommended: Our pick of Bo Diddley Hits.

10. Love Is Strange

Chances are you were most likely introduced to ‘Love Is Strange’ while watching the iconic film Dirty Dancing as Patrick Swayze and Jennifer Grey flirtatiously danced together for the first time in a private room. You didn’t hear Holly’s deep voice wafting out of the movie screen though, you heard the duo Mickey & Sylvia, who had a taste of fame with this hit song in 1955, long before Dirty Dancing ever debuted. Buddy Holly was an original triple threat, an artist who could write, sing, and play his own songs. While most of his releases were original, he occasionally recorded covers, and ‘Love Is Strange’ is one of his more popular efforts, coming in lower on our list at 10.

Recommended listen: Our write-up of the Dirty Dancing soundtrack (yes, really.)

9. You’re So Square (Baby, I Don’t Care)

Elvis Presley was one of Buddy Holly’s biggest influences, and the king of rock and roll’s impact is felt the most in Holly’s cover of ‘You’re So Square (Baby, I Don’t Care).’ Elvis originally recorded it in 1956, and Buddy chose it as one of his picks to ultimately include on a self-titled album he worked on throughout ’57 and ’58. For this track, Holly’s vocals oscillate between powerful tenor and silky baritone, something Elvis often did with his music. Even the production has that Sun Records vibe so sought after in the ’50s. The label was the first to give Elvis a studio home. Though the song fits the rock genre, like so many Sun Records recordings, Holly’s vocals are at the forefront breathy and crystal clear, while rhythmic instruments are relegated to the background, used only for support. This is one of a string of covers Holly recorded as he built up his catalog in the late ’50s, a beautiful take on an early Elvis song, and it comes in at number 9 on our playlist.

8. It Doesn’t Matter Anymore

Recorded during the same session as ‘True Love Ways,’ this fun, bouncy track was written by singer-songwriter Paul Anka. Conductor Dick Jacobs once again commands an immaculate orchestra, with the springy strings section bringing fresh air to the tune. Holly adds to this spring-like renewal by occasionally utilizing his vocal “hiccup” technique. Popping up in random places on the track, you have to smile when you hear it because it adds such an adorable flair. The song is all about learning to move on after heartbreak, and Anka wrote it specifically for Buddy, which is one of the reasons why ‘It Doesn’t Matter Anymore’ has such a natural feel to it. Since it was one of the last songs Buddy would record, Anka donated all the songwriter royalties he received to Holly’s widow, Marie.

7. (Ummmm, Oh Yeah) Dearest

Featured on the compilation album Giant, ‘(Ummm, Oh Yeah) Dearest’ is one of Holly’s many recordings released after his death. The way the Giant album came about is very interesting, especially since it was done before the music industry experienced the technological wave that ushered in digital-based production. The album features all types of guest artists, including Waylon Jennings who knew Holly well. This particular track features 1950s band The Fireballs. Holly’s producer Norman Petty brought them into the studio to overdub their own parts over Holly’s original demo recordings, creating a brand new finished work. Their efforts had to be flawless, and the entire project took Petty several years to complete. This number has the same fun syncopated rock rhythm as ‘Words of Love.’

6. Rave On

Coming in halfway through at number 6 is ‘Rave On,’ a blues shuffle single that’s a shoo-in for any top ten Buddy Holly playlist. One of the rare tunes Holly didn’t write himself, he almost didn’t get the chance to record the upbeat rock ‘n roll classic. Songwriting trio Sonny West, Bill Tilghman and Norman Petty (who was also Holly’s producer) wanted to pass off the song to another group who they thought would be a better fit for the ’50s party anthem. But Holly could be very persuasive and he ultimately talked them into giving his act first dibs. Released in 1958 on The Buddy Holly Story album, the UK loved the single, taking it all the way to #5 on the charts. The rocking hit features one of Buddy’s signature vocal techniques, the “hiccup,” which allowed him to put emphasis on certain words and give his lyrics a rich personality. Future stars like Michael Jackson would go on to incorporate this surprisingly tough-to-tackle vocal technique in their recordings as well.

5. True Love Ways

Buddy Holly gives Frank Sinatra a run for his money with this big band recording. A deviation from Holly’s traditional early rock setup, the original recording of ‘True Love Ways’ features full orchestral instrumentation headed up by conductor Dick Jacobs, who worked with several big-name acts throughout the ’50s. The strings and sax give the tune a charming and nostalgic feel. Holly meticulously adds to this by going heavy on the vibrato with his voice, exhibiting expert control at just 22 years old. This recording session would be his last before his untimely and tragic death in a small plane accident. The single was released posthumously and many years later his wife Maria told reporters it was written about their relationship. The two fell so hard for each other they became engaged on their first date, and you can definitely hear this sentiment in Holly’s performance.

4. Peggy Sue

The name “Cindy Lou” conjurs up images of Dr. Suess holiday classic How The Grinch Stole Christmas featuring the story’s loveable protagonist Cindy Lou Who. So it’s a good thing Buddy Holly’s drummer, Jerry Allison, convinced his band leader to change this song’s name from “Cindy Lou” to “Peggy Sue,” in an effort to win back a girl he had gone out with who stole his heart. The gimmick worked. Not only did the song help Allison get his girl back, it proved to be a huge hit at home and abroad. Another fun fact about this track has to do with the light tension felt from start to finish. The beat was originally supposed to have a “cha-cha” feel, but Allison couldn’t get it down during the takes. When production jokingly threatened to change the name of the tune back to “Cindy Lou” if he couldn’t get it, he started messing around on the drums to loosen up his muscles. As he played around with marching band rhythms from high school, Holly actually liked that better, and he re-recorded the song around the new beat.

Related: This track appears on our playlist of amazing rock and roll songs.

3. Words Of Love

One of Holly’s more obscure songs while he was alive, harmony is at the forefront of this track while steady electric guitar rhythm and lead holds it down. The guitar riff played at the beginning of the song serves as a motif throughout, and listeners will find themselves humming the guitar parts just as much as the lyrical melodies after listening to it. A really interesting aspect of ‘Words of Love’ can be found in Holly’s recording process for the single. Harmonies weren’t nearly as easy to record back in the ’50s, but he knew he wanted harmony parts for the vocals so he overlayed tapes of his own recorded harmonies on top of each other. The method was a bit primitive, and it gives the tune a haunting feel. Its got staying power and posthumously became a fan favorite for Holly, that’s why it comes in at number 3 on our list.

2. Everyday

Though Holly was known for his signature Fender Strat he always sported on stage, he laid it down for this intimate, short track featuring nothing but light percussion work, Holly’s voice, and a few odd instrument choices that proved to be ingenious over time. In the ’50s, songs were still produced via “analog” recordings, so actual tape instead of the digital files we have now. Back in the day, this meant that band’s recorded takes all at once together, not in piecemeal fashion like modern times. ‘Everyday’ wasn’t a traditional rock song though. It required a hushed feel that helped drive home its intimacy. To keep the beat, Jerry Allison put down his sticks and gently tapped the side of his thigh to keep rhythm. The other oddball? A Celesta, which you can hear throughout the track, adding what sounds like bells to the background. It gives the popular tune an almost-lullaby type feeling. Holly’s classic, one-of-a-kind “stutter vocal” technique is on full display as well. The song wasn’t a hit, but all of these obscure musical stylings put together created a timeless masterpiece music lovers play on repeat to this day. ‘Everyday’ takes the second spot on our list, just behind Holly’s only number 1 hit. Can you guess what that is? Read on to find out.

1. That’ll Be The Day

Buddy Holly had to fight for his trademark hit, ‘That’ll Be The Day,’ to ever see the light of day. He and his drummer Jerry Allison knew they had a chart-topper on their hands, a designation they had been chasing for years. But their label didn’t see its potential. Once they were under new management at producer Norman Petty’s studio in New Mexico, they re-recorded the track and released it. The rocker quickly shot up the charts to number one in both the US and UK. Like ‘Rave On,’ this grooving number features a shuffle rhythm. Holly pulled out all his signature stops for the tune, including his unique vocal stutters and hiccups fans were known to love. One listen to ‘That’ll Be The Day’ and you understand why Holly is credited as not only a pioneering force in early rock music, but the guy who came up with the classic rock band setup: two guitars, a drum kit, and a thumping bass. Its catchy lyrics and melody will be stuck in your head all day!

Recommended: Our selection of classic rock and roll songs (including this one!)

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About Ged Richardson

Ged Richardson is the Founder and Editor-in-Chief of He has been featured in Entrepreneur, PremierGuitar, Hallmark, Wanderlust, CreativeLive, and other major publications. As an avid music fan, he spends his time researching and writing about new and old music, as well as testing and reviewing music-related products. He's played guitar in various bands, from rock to gypsy jazz. Be sure to check out his YouTube channel, where he geeks out about his favorite bands.

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