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Best Famous Crooners of the 50s and 60s

What do Nat King Cole, Bing Crosby, Frank Sinatra, Dean Martin, and Sammy Davis Jr. all have in common? Well, in case you didn’t grow up in the Baby Boomer generation, these famous names were all incredibly popular crooners who enjoyed immense success, especially during the 1950s and 1960s.

A crooner is considered to be a singer – usually male – who sings softly, slowly, and, more often than not, sentimentally. Some of the best crooners in musical history were those that belted out jazz standards.

Crooners like Ol’ Blue Eyes, Frank Sinatra, typically would perform in large, smoke-filled ballrooms full of people gently swaying to their melodies. Their songs would emphasize their strong vocals and would revolve around themes of love and loss. The crooners of the mid-20th century were some of the most well-known hopeless romantics of their day. After all, there’s a good reason why croon rhymes with swoon.

While folks like Michael Buble, Hugh Coltman, and Howe Gelb have been steadfastly keeping the crooner torch aflame in modern times, there is no denying the fact that the definitive Golden Age of the crooner was the 1950s and 1960s. 

Join us as we take a loving look back at some of the best crooners from this bygone era.

Facts Verse Presents: Best Famous Crooners of the 50s and 60s

Bing Crosby

Crosby’s bass-baritone voice was inspirational to many crooners that we’ll be discussing in the next few minutes. From 1934 to 1954, Crosby led the charts in record sales, box-office earnings, and radio ratings.

He got his start performing with a band called the Rhythm Boys, but after outshining his bandmates, he rose to fame with songs like “Just One More Chance”, “I Found a Million Dollar Baby”, “Out Of Nowhere”, and “At Your Command”.

Crosby’s voice defied traditional singing conventions. He was innovative and consistent and was even one of the first artists to inspire the coining of the term ‘Crooning’.

Crosby died on October 14, 1977, and not long after, was posthumously inducted into the Grammy Hall of Fame.

Dean Martin

Born Dino Paul Crocetti in 1917, the “King of Cool”, Dean Martin was a singer who always seemed to make it look easy. From a distance, Martin might have appeared to be a bit lazy, but in reality, during the 1940s and 1950s, he worked his backside off to became a great crooner like his heroes, The Mills Brothers and Bing Crosby.

Martin received widespread recognition teaming up with Jerry Lewis to form a comedy team. In 1956, Martin and Lewis split up, but both stars went on to achieve greatness.

Dean became a megastar with numerous hit songs like “That’s Amore”, “Sway”, “Memories Are Made of This”, and “Volare”. Beyond the music industry, Martin was also one of the biggest TV stars of his time, headlining his very own variety show from 1965 to 1974. 

Sadly, Dean was never quite the same after his beloved son was killed in 1987. Several years later, he passed away on Christmas Day 1995.

Frank Sinatra

If you’ve never heard of Frank Sinatra before, then you’ve obviously been living under a rock. The “Chairman of the Board” as he was known by his Rat Pack buddies, was the heartthrob of many around the globe. However, it wasn’t just his dashing good looks and debonair demeanor that made him the envy of many. Sinatra’s melodious baritone voice, coupled with his spellbinding lyrics, earned him over 30 awards and accolades, including 3 Oscars and 13 Grammys

Some of Frank’s biggest tunes included “Fly Me To The Moon”, “New York, New York”, “Moon River”, “High Hopes”, and “I Did It My Way”. Listening to these songs today still takes you back to a warmer and happier time in pop culture history.

Sinatra enjoyed a strong following in the 1950s and 60s, but he continued to find success right up until shortly before his death on May 14, 1998.

Dick Haymes

This crooner burst onto the music scene in the early 40s after putting his time in as a vocalist with The Harry James and Tommy Dorsey Orchestra. With his rich, moving, and deeply soulful baritone voice, he put out hits like “You’ll Never Know”, “It Might As Well Be Spring”, and “Little White Lies’.

Haymes signed a multi-record deal with Decca Records and was given second choice of songs following the studio’s main crooner at the time, Bing Crosby. Sadly, Haymes struggled with alcohol for many years and had several failed marriages, but his voice remained strong and moving right up until his death from lung cancer in 1980.

Tony Martin

Tony’s musical career began in the mid-30 when he emerged as a confident and engaging singer. He had numerous hit songs throughout his lengthy career, such as “Tenement Symphony”,  “It’s A Blue World”, “Stranger in Paradise”, “I Get Ideas”, and “All The Thing You Are”.

In his later years, Martin faced a great deal of heartache. His beloved wife of decades, Cyd Charisse, passed away in 2008. Just three years later, his only son, Tony Martin Jr, died as well. The following year Tony himself passed away at the age of 98.

Buddy Clark

For many years, Buddy Clark was a successful radio and Big Band singer. He had the charisma of a movie star, but unfortunately, he didn’t have the looks of one. In 1946, he signed a recording contract with Columbia Records and not long after scored his most significant career hit with the track “Linda”. In 1947, Clark had several more hits, including “How Are Things in Glocca Morra”, “Peg O’ My Heart”, “I’ll Dance At Your Wedding”, and “An Apple Blossom Wedding”. A year later, he had another big hit on his hands with the song “Love Somebody”, a duet that he did with Doris Day.

Clark tragically died in a plane crash on October 1, 1949, but his music continued to be enjoyed by countless fans throughout the 1950s and 1960s. Even to this day,  his music continues to inspire.

Billy Eckstine

This legendary singer was born in Pittsburgh, Pennsylvania, in 1914. He had a smooth-as-butter voice and the looks to suit. Eckstine did a ton of live performances touring with Sarah Vaughan. A few of his most significant hits include “I Apologize”, “My Foolish Heart”, “I Get A Kick Out Of You”, and “Ev’ry Time We Say Goodbye”.

In the 1960s and 1970s, Eckstine recorded for Motown Records as well as several smaller labels, but the peak of career was clearly in the 1950s. Still, his voice never wavered.

He continued to perform well into his golden years. He retired in 1990 and died in Pittsburgh on March 8, 1993, at 78.

Bobby Darin

This crooner somehow managed to cram more living into his brief 37 years on earth than most people are capable of doing in their entire lifetimes. He first found success in the music industry with his hit song “Splish Splash” which was released in 1958.

Darin had dreams of outshining his idol Frank Sinatra, and in many ways, he was more of a dynamic performer than Frank was. Some of Darin’s most celebrated songs were “Mack The Knife”, “Artificial Flowers”, and “Beyond the Sea”.

Much like the majority of his fellow crooners, Darin acted in films and was a top draw in Vegas. While his life was ultimately cut short, he recorded countless albums.

Bobby ended up dying in 1973 from complications of heart surgery.

Rudy Vallee

Vallee started off as a drummer, saxophonist, and clarinetist. He made early attempts at vocalization, but these were all shot down. Eventually, however, his tenor voice caught the attention of masses. Combined with his personality, charm, and handsome looks, he earned himself countless fans.

In the 1920s, “Flappers” flocked to him almost religiously, and he wound up becoming one of the first mass media pop artists and crooners to receive widespread attention.

Vallee continued to find success throughout the 50s, 60s, 70s, and well into the 80s. A few of his best-known songs include “Life is Just a Bowl of Cherries”, “Violets”, “As Time Goes By”, and “The Whiffenpoof Song”.

Nat King Cole

Born Nathaniel Adams Cole on March 17, 1919, this crooner got his start as a wildly popular jazz pianist before people started to realize that he also had very distinct singing voice. His melodic baritone takes on popular songs of the day, coupled with his fantastic playing skills, earned him a great deal of distinction.

A few of Nat King Cole’s best-known songs include “Straighten Up and Fly Right”, “Route 66”, “Mona Lisa”, Nature Boy”, “Too Young”, “The Christmas Song”, and “Those Lazy Hazy Crazy Days of Summer”.

For his contributions to the world of music, Cole has been inducted into the Grammy Hall Of Fame, the Rock and Roll Hall of Fame, and The Jazz Hall of Fame.

Tony Bennett

Last but not least, we have a crooner who first found success in the 50s and 60s but went on to enjoy continued success to the present day. Born Anthony Dominick Benedetto, Tony Bennett served in the Second World War and spent some time as a painter before taking the music world by storm with hit songs like “I Left My heart In San Francisco”, “Because of You”, “Rags To Riches”, “I Wanna Be Around”, and “Blue Velvet”.

Throughout his celebrated career, Bennett has put out 61 studio albums, mainly consisting of jazz standards and pop songs. He’s won 17 Grammys and has been honored with the Grammy Lifetime Achievement Award. He is also the founder of the prestigious Frank Sinatra School of Arts in New York.

On August 5, 2021, Bennett gave his final performance at Radio City Music Hall. That same year, it was revealed that he had been diagnosed with Alzheimer’s disease in 2016.

The age of the crooner might be long past, but the music that was created by the men we just discussed is timeless. It’s safe to say that even twenty or thirty years from now, people will still be listening to the music of folks like Dean Martin, Frank Sinatra, and Bing Crosby. After all, those singers really were at the top of their class.

Looking back at the crooners that were popular throughout the 1950s and 1960s, it’s difficult to say who was “the best”, as they all shined brightly in their own unique ways. That being said, we’re willing to bet that you have a few favorites.

Who do you think was the best crooner of the 50s and 60s and do you think the genre of music that the crooners of yesteryear helped popularize will ever see a resurgence? Let us know in the comments, and as always, thanks for watching!

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