Past Grammy Award Winners & Performers in History

Created on Feb 10, 2017 by Kathy Pinna

Music makes our hearts soar, brings us joy when we're depressed, puts a twinkle in our eyes, makes us dance - and singing is a good workout for our lungs!

Music is the soundtrack of our lives. Have you ever heard a song and it takes you back in time to the first time that you heard it? You know where you were, who you were with, and what you were doing.

Checkout this musical photo collection of entertainers from the past. Do you remember the first time you heard them?

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Lena Horne

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Lena Horne (1917 - 2010), at left - singer, dancer, actress, and civil rights activist - was nominated for 7 Grammy Awards and won 4 times - once for the Hall of Fame Award and once for Lifetime Achievement. She began performing at the age of 16 at the famous Cotton Club and kept performing for 70 years!

David Bowie

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Singer, songwriter, musician, record producer, actor, and artist, David Bowie (1947 - 2016) was nominated for 10 Grammys and won once. He also won the Lifetime Achievement Award. In addition, he won an Emmy and an MTV Award and was nominated for numerous other awards and honors. He's up for 5 Grammy Awards this year (2017) although he died in 2016.

Frank Sinatra

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Francis Albert "Frank" Sinatra (1915 - 1998) was a singer, actor, and producer. He won 11 Grammy Awards and was nominated for numerous more and he has been called "the greatest singer of the 20th Century." He even won the Academy Award in 1953 (and was nominated for another in 1955)!


Josephine Baker

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Born in St. Louis, Missouri, Josephine Baker became a sensation in Paris, France. A singer and dancer, she refused to perform for segregated audiences and moved to France where racism was not an impediment to her career. She was a famed part of the Jazz age and later renounced her American citizenship. This is a tame photo of her - her costumes were very racy - one of the most noted consisted of a girdle of bananas and nothing else!

Although she didn't win a Grammy, she was awarded the Croix de Guerre, Légion d'Honneur and the Rosette of the Résistance for her efforts in the French Resistance in World War II.

Bing Crosby

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Bing Crosby (1903 - 1977) was awarded 5 Hall of Fame Grammy Awards (for White Christmas, Brother Can You Spare a Dime, Swinging on a Star, Don't Fence Me In, and Pennies From Heaven) and a Lifetime Achievement Award in 1962. He was one of the best-selling recording artists of the 20th century. His films with Bob Hope were classics, too.

Sammy Davis, Jr.

with President Richard Nixon
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Singer, dancer, actor, comedian, impressionist - Sammy Davis Jr (1925 - 1990) could do it all. He was nominated for 3 Grammy Awards but never won. He was, however, awarded 2 special Grammy awards - one for Lifetime Achievement and the Hall of Fame Award.

Paul McCartney

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Paul McCartney (born 1942) is still alive, of course, but his work as a Beatle and on his own has been part of the soundtrack of many Baby Boomers' lives. He has won 18 Grammy Awards (and nominated many more times) and has two Grammy Lifetime Achievement Awards - one as a Beatle in 2014 and one himself in 1990. The Beatles publicly broke up in April, 1970.


B.B. King

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Born Riley B. King, B.B. King (1925 - 2015) was a blues singer, guitarist, songwriter, and record producer. Nominated for 18 Grammy Awards, he lost only 6 times. He was the son of sharecroppers and raised by his grandmother and taught himself the guitar. There will only ever be one B.B.!

Elvis Presley

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Elvis Presley (1935 - 1977) was called "The King of Rock and Roll" for good reason. He is still adored by many - almost 40 years after his death. A singer, musician, and sometimes actor, he introduced mainstream America to rock n' roll - Heartbreak Hotel was released in 1956. He was awarded 6 Hall of Fame Grammy Awards (for Are You Lonesome Tonight, Don't Be Cruel, Suspicious Minds, That's All Right Momma, Heartbreak Hotel, and Hound Dog).

Michael Jackson

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The "King of Pop." Michael Jackson (1958 - 2009) began his career as one of the Jackson Five (his brothers) at the age of 6 and began his solo career in 1971. His album Thriller remains the best selling album of all time. Not only was he a singer, dancer, songwriter, and record producer, he also had a great influence on fashion! He won 13 Grammy Awards and was nominated for countless more. (He won 8 Grammys for Thriller.)

Bob Dylan

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Born Robert Allen Zimmerman in 1941, some may not consider Bob Dylan much of a singer. But he has 12 Grammy Awards (and been nominated for over twice that) and has performed his own songs for over 55 years. He was awarded a Nobel Prize for Literature in 2016 "for having created new poetic expressions within the great American song tradition".

Marian Anderson

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Marian Anderson (1897 - 1993) was an amazing singer. She was awarded 4 Grammys - 1 Lifetime Achievement Award and 3 Hall of Fame Awards (for My Country 'Tis of Thee, He's Got the Whole World in His Hands, and Ave Maria.) She was also active in Civil Rights. When the DAR refused permission for her to sing in Constitution Hall in front of an integrated audience (1939), she (helped by FDR and Eleanor Roosevelt) performed an open air concert on the steps of the Lincoln Memorial.

History of the Grammy The 1st Annual Grammy Awards were held on May 4, 1959, recognizing the musical accomplishments by performers for the year 1958. Domenico Modugno, Henry Mancini, Ella Fitzgerald and Ross Bagdasarian, Sr. each won 2 awards. (Do you know them?) Stevie Wonder came along in the 1960's and holds the title for the most Grammys awarded to a solo male artist. (Currently, 22 awards.) Singer Alison Krauss has won 26 Grammy Awards, making her the most honored female solo artist in the history of the ceremony. And old blue eyes won 11 Grammys.

Have photos that you'd like to see included? Share your photos, or click "next page" to see "Old-Time Music Bands".

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