3 Eternal Classic Rock Songs from Music’s Biggest “What If”: Buddy Holly

Pop music’s biggest what if remains Buddy Holly. While the sonic landscape is sadly rife with artists who died too early, Holly passed away in a plane crash at just 22 years old. Not only does he boast several all-time songs but his influence ranges from Paul McCartney to Bob Dylan to The Rolling Stones to Weezer and Elton John.

Here below, we wanted to explore three hits Holly wrote. A trio of tunes that remind us both of what he was and what we lost when he passed away with three others in a plane crash in Iowa on February 3, 1959, or as Don McLean sang, the “day the music died.” Indeed, these are three eternal songs from music’s biggest “what if,” Buddy Holly.

[RELATED: 3 Forever Artists Who Died Too Soon in the 1950s]

“That’ll Be the Day” from The “Chirping” Crickets (1957)

This song released by Holly’s band The Crickets was the group’s only LP that came out during Holly’s brief lifetime. It’s not hard to imagine this song playing on every rock radio station in the 1950s and at every teen dance of the era, too. On the track, which hit No. 1 on the Billboard Hot 100, the bespectacled Holly sings about a prospective breakup, saying that when the relationship ends, he’ll feel as if he’ll die. On the track, he croons,

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

Well, you gave me all your loving

And your turtle doving

All your hugs and kisses

And your money too

You know you love me, baby

Still you tell me maybe

That someday well

I’ll be through

“Everyday” from Buddy Holly (1958)

From Holly’s debut self-titled solo studio album, this track is perhaps his most famous. Short and sweet, Holly sings over a pitter-patter of hand claps. The song, which hit No. 3 on the Billboard Hot 100, has since been featured in countless movies and television shows and covered many times, including by John Denver, James Taylor, Fiona Apple and Don McLean. On the song, Holly sings about the glories of fresh love, offering,

Everyday, it’s a-gettin’ closer

Goin’ faster than a roller coaster

Love like yours will surely come my way

A-hey, a-hey, hey

Everyday, it’s a-gettin’ faster

Everyone said, “Go up and ask her”

Love like yours will surely come my way

A-hey, a-hey, hey

“It Doesn’t Matter Anymore” from The Buddy Holly Story (1959)

You can hear so many influences in this song and imagine the ripple effects from it. There is country, rockabilly, proto-rock and roll, blues, and more. And you can hear just what the world lost, from a star songwriter to a rival to others like Elvis Presley. Released on Holly’s 1959 LP The Buddy Holly Story, this track, which hit No. 13 on the Billboard Hot 100, came out just a month before he died in that horrible crash. Noting the tragic irony of the song, its writer, Paul Anka, has donated all the royalties from the track to Holly’s family. On it, Holly sings,

There you go and baby here am I

Well you left me here so I could sit and cry

Well, golly gee what have you done to me

Well I guess it doesn’t matter anymore

Do you remember baby, last September

How you held me tight, each and every night

Well oops-a-daisy, how you drove me crazy

But I guess it doesn’t matter anymore

When you purchase through links on our site, we may earn an affiliate commission.

Photo by Evening Standard/Hulton Archive/Getty Images