31 Best Songs From 1958

“Oh Lonesome Me” by Don Gibson

Song Year: 1958

When you’re alone, it’s easy to notice all the happy couples around you who are having the best time. They like to go out, paint the town, and have a few laughs almost every night.

Meanwhile, you’re stuck at home with nothing but your thoughts. Self-pity becomes easy when you realize that the perfect woman left you and that you’ll never find someone as wonderful as she was.

“Don’t Ask Me Why” by Elvis Presley

Song Year: 1958

Elvis had a wide range of talents, making his songs highly relatable. He was a master of upbeat dancing tunes and similarly adept at heartbreaking songs about loneliness.

Anyone could listen to Elvis and get into it.

In “Don’t Ask Me Why,” he tells his woman that he’ll love her no matter what. Even though he knows she’s bad for him and that she might leave him one day, he cannot help but keep loving her.

“Summertime Blues” by Eddie Cochran

Song Year: 1958

Bad news hits a little differently when you’ve been working hard trying to get ready for a big summer bash or a date with your special lady.

If your boss swoops in and says you have no choice but to work the late shift, what are you supposed to do?

It’s a shame young folks can’t enjoy their summer vacation. Eddie Cochran croons about this tragedy in an upbeat tune later covered by Alan Jackson.

“La Bamba” by Ritchie Valens

Song Year: 1958

Ritchie Valens didn’t write “La Bamba,” but he did make it popular outside of the Mexican state of Veracruz.

Valens took a traditional Mexican folk song and turned it into a popular American rock and roll song.

It hit the top 40 when it got released in 1958 and routinely appears on Rolling Stone’s list of the best songs of all time.

“Lonely Teardrops” by Jackie Wilson

Song Year: 1958

Jackie Wilson and his doo-wop background singers make “Lonely Teardrops” the happiest sad song of all time.

It’s hard to feel down when such an upbeat song is playing in the background.

Wilson’s flawless vocals pair perfectly with complicated harmonies and a driving beat. The listener almost forgets that he’s singing about his loneliness.

“It’s Only Make Believe” by Conway Twitty

Song Year: 1958

Conway Twitty was a star in the country music world, especially among young women who thought he was dreamy.

In this song, Twitty is a man who is hopelessly in love with a woman who doesn’t love him back.

He seems to channel a little bit of Elvis Presley in “It’s Only Make Believe.” But he brings his depth and emotion to the tune.

“What Am I Living For” by Chuck Willis

Song Year: 1958

It’s a painful thing to lose your reason for living. Chuck Willis explains how hard it is to move on when your reason for getting out of bed in the morning has left you.

You can’t find something to replace it; you can’t just get over the heartache. The pain and hurt swallow up your energy and your focus.

How can you go on when the person you lived for doesn’t love you anymore?

“(Night Time Is) The Right Time” by Ray Charles

Song Year: 1958

Ray Charles was a master on the keyboard, and he wrote some of the most well-regarded music of his day. He had a sleek, sexy style that made him easy to listen to and easy to love.

In songs like “(Night Time Is) The Right Time,” he lets all of his personality and spunkiness show. He knows what he wants and is not afraid to go after it.

At the end of a long day, he wants his baby by his side.

“One For My Baby (and One More For the Road)” by Frank Sinatra

Song Year: 1958

Frank Sinatra was bound to appear on this list sooner or later. He dominated the music industry for a long time with hits like “One For My Baby.”

In this particular song, Sinatra appears as a lonely barfly looking to share his burdens with the local bartender. He doesn’t feel so good, and his deep suspicion is that the experienced barman can help him.

“I Wonder Why” by Dion & the Belmonts

Song Year: 1958

Dion & the Belmonts were a pop sensation in the late 50s and 60s. They were one of the top boy bands of their day.

With slick harmonies and boyish charm, they sing about the curiosity of love. It’s impossible to control who you fall in love with, and sometimes it confuses you.

You don’t always know why you love someone; all you know is that you do.