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25 Best Pop Songs from the Late Fifties

1957, Doris Day, Harry Belafonte, Pat Boone, The Fifties

The cultural impact of rock ‘n’ roll was so dramatic that it completely eclipsed the under-appreciated EASY-POP music of the fifties. Appearing as early as 1948 and still being recorded late into the century, quintessential EASY-POP recordings peaked in the nineteen-fifties. But during this single decade there was an astonishing variety of sparkling singers, infectious arrangements, and catchy lyrics that produced recordings much more innovative than the sum of their parts. No single recording typifies the decade. To capture the gist of the 50s EASY-POP genre you need to synthesize the unique sound by listening to a selection of quintessential recordings. Here are twenty-five archetypical songs and singers that epitomize the EASY-POP sound during the second half of the fifties.

Sincerely McGuire Sisters 1955
Like the Andrews Sisters, the prototypical sister group, the McGuire sisters had a string of hits: Sugartime, Muskrat Ramble, Something’s Gotta Give, and May You Always.

Memories Are Made of This Dean Martin 1955
Dean Martin was backed by the Easy Riders singing ‘sweet sweet’ on this breezy song offering a recipe for fifties life-a girl, a boy, some grief, some joy. It was from the film ‘The Seven Hills Of Rome’ where it was sung by Mario Lanza.

How Important Can It Be? Joni James 1955
Youthful Joni James reflects the feelings of fifties teenage girls in this song questioning the importance of past romantic relationships to a new-found love.

Moments to Remember Four Lads 1955
The Four Lads’ Moments to Remember in 1955, No, Not Much in 1956, Put a Light in the Window in 1957, and There’s Only One of You in 1958 were all stylish, catchy, easy-to-sing-along-with classic fifties hits. Quartet harmony was also heard in recordings from the Four Aces, the Four Preps, the Four Coins, the Crew-Cuts, and the Ames Brothers.

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Learnin’ the Blues Frank Sinatra 1955
One of a dozen classy Frank Sinatra hits, this lightly, bluesy song is in the same vain as Dinah Shore’s Blues in Advance, and Ella Mae Morse’s Blacksmith Blues.

The Breeze and I Caterina Valente 1955
This wistful song in which the singer laments that only the Breeze and I are aware of her love begins with castinets and “la-la-la”. The song was originally written as Andalucia, and it was a 1940 hit for Jimmy Dorsey with Bob Eberly.

Moonlight Gambler Frankie Laine 1956
Frankie Laine’s brash vibrancy and dynamic style, gambling on love, was evident on Moonlight Gambler, the final hit release of his twenty-year career.

Whatever Will Be, Will Be (Que Sera) Doris Day 1956
Alfred Hitchcock assigned the gifted team of Jay Livingston and Ray Evans to write a simple lullaby for his suspense film ‘The Man Who Knew Too Much’ and it proved to be the biggest hit of Doris Day’s recording career. Que Sera, Sera received the 1956 Academy Award for best original song.

Wayward Wind Gogi Grant 1956
This haunting, philosophical 50s lyrical ballad was a beguiling anthem for the restless.

Ivory Tower Cathy Carr 1956
This only hit song for Cathy Carr was a cover of an original recording by the R&B; group the Charms. Gale Storm also covered it. All were top-ten hits.

(Let Me Be Your) Teddy Bear Elvis Presley 1957
Elvis Presley, Ricky Nelson, Buddy Holly, and other rock idols, scored with mainstream EASY-POP songs in addition to their rock ‘n’ roll hits.

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Round and Round Perry Como 1957
Relaxed and amiable Perry Como was a singer who didn’t have to prove anything with his voice-no fuss, no affect, no attitude. The quintessential, exhilarating Round and Round was on the charts for more than half of 1957.

Chances Are Johnny Mathis 1957
Johnny Mathis typifies the skillful, silky, gentle, and tender side of the fifties sound.

April Love Pat Boone 1957
With his white buck shoes and clean-cut image, smooth baritone Pat Boone’s lilting title song from his popular film ‘April Love’ was nominated for an Academy Award.

Tammy Debbie Reynolds 1957
She heard the cottonwoods whispering above in the title song from the film ‘Tammy and the Bachelor.’ It was the only number one hit for America’s sweetheart and popular film star Debbie Reynolds.

Banana Boat Song (Day-O) and Island in the Sun Harry Belafonte 1957
Harry Belafonte brought a calypso sound to the fifties music scene.

Catch a Falling Star Perry Como 1958
The Ray Charles singers back Perry Como again on this Joe Reisman arrangement that was based on a classical theme from Brahms’ Academic Festival Overture. The first-ever ‘gold record’ was awarded to Catch a Falling Star. It was the last number one hit for the decade’s favorite singer.

Lollipop Chordettes 1958
The penultimate girl group, the Chordettes, had a #1 hit with Mr. Sandman in 1954 and then recorded this classic ‘lolly lolly lollypop’ hit. The Fontane Sisters had a similar ‘do do wah, do do wah’ hit with Hearts of Stone.

Oh! Oh! I’m Falling in Love Again Jimmie Rodgers 1958
Jimmie Rodgers, along with the Weavers and the Everly Brothers embody a folk touch in several fifties EASY-POP songs.

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26 Miles (Santa Catalina) Four Preps 1958
The youthful image of summertime fun on the beach was captured by the Four Preps in 26 Miles, by Jerry Kellor in Here Comes Summer, and by the Jamies in Summertime.

Everybody Loves a Lover Doris Day 1958
This recording utilizes the double-track voice overdub technique frequently heard in the 50s. Doris Day, Jo Stafford, Patti Page, Dinah Shore, Margaret Whiting, Peggy Lee, Sarah Vaughan, Georgia Gibbs, and others recorded these lively, upbeat, girlish hits.

Venus Frankie Avalon 1959
From the angelic choir’s opening notes, Venus, a prayer to the goddess for a girlfriend, was the first #1 hit for Frankie Avalon.

The Three Bells Browns 1959
The bells rang first for Jimmy Browns’ birth, then again for his marriage and finally his death in this pop/folk song from Maxine, Bonnie and Jim Ed Brown. It was based on a song called While The Angelus Was Ringing, a hit in France for both Les Compagnons De La Chanson and Edith Piaf.

Mack the Knife Bobby Darin 1959
Mack the Knife, written in 1928 as Moritat or Theme from the Threepenny Opera, became Bobby Darin’s signature song. ‘Mack’ is the character Macheath, the murderer, in The Threepenny Opera. The light melody feels like an upbeat song, but it contrasts sharply with the lyrics about a criminal.

Dream Lover Bobby Darin 1959
Bobby Darin, Paul Anka, Pat Boone, Sam Cooke, and Frankie Avalon were pop idols late in the decade.