19 Best Singers Like Frank Sinatra

Ella Fitzgerald

American jazz singer Ella “Queen of Jazz” Fitzgerald is one of the most important figures in jazz music you can name. She initially found success with the Chick Webb Orchestra. She would go on to launch her illustrious solo career in 1942.

Fitzgerald and Sinatra shared a stage on multiple occasions. Fitzgerald even sang on The Frank Sinatra Show. Fitzgerald had always wanted to record a studio or live album with Sinatra, but alas, this dream never came to pass.

For some classic Fitzgerald moments, explore “Cheek To Cheek,” “It Don’t Mean a Thing,” “These Foolish Things,” “Misty,” and “Summertime.”

Doris Day

American actress, singer, and animal rights activist Doris Day started out as a big band singer in 1939. In 1945, “Sentimental Journey” and “My Dreams Are Getting Better All the Time” shot to the top of the charts. This gave Day the clout she needed to leave Les Brown & His Band of Renown to pursue a solo career.

Over the course of a 20-year career, Day would record 650+ songs(!).

Les Brown said Day belonged in the same company as Frank Sinatra and Bing Crosby. She would also star in Young at Heart alongside Frank Sinatra.

For an education in Doris Day, listen to “Dream A Little Dream Of Me,” “Perhaps Perhaps Perhaps,” “Secret Love,” “It’s Magic,” and “Everybody Loves A Lover.”

Julie London

American singer and actress Julie London was a prolific artist, recording 30+ albums of pop and jazz standards. London was inducted into the Grammy Hall of Fame, and she was even nominated for a Golden Globe Award.

London was stunning in every way imaginable, and her whisper-sing style is still sexier than most modern songstresses can ever hope to be.

If in doubt, reference “Cry Me a River,” “I’m In The Mood For Love,” “My Heart Belongs to Daddy,” and “I’m Glad There Is You.”

Peggy Lee

American singer, songwriter, composer, and actress Peggy Lee would have her first top 10 hit in 1942 with “Somebody Else Is Taking My Place.” As with many of her peers, Lee remained incredibly prolific throughout her career, recording over 1,100 songs, and composing more than 270.

Peggy Lee and Frank Sinatra would perform together on many occasions, much to the delight of watching and listening audiences.

Some of her career highlights include “Fever,” “Why Don’t You Do Right,” “It’s A Good Day,” and “Sing A Rainbow.”

Rosemary Clooney

American singer and actress Rosemary Clooney found fame in the early 1950s with “Come On-a My House.” Clooney would go on to enjoy success both as a pop and jazz vocalist. She had a bit of a rough go in the 1960s due to drug addiction and depression but made a successful comeback in 1977.

Clooney was good friends with Crosby, whose show she often appeared on.

Some standout moments of hers include “Botch-a-Me,” “Mambo Italiano,” “Me and My Teddy Bear,” and “Oh, You Beautiful Doll.”

Jimmy Durante

American comedian, actor, singer, and pianist Jimmy Durante became a familiar face in the 1920s and remained that way even into the 1970s. His big nose, gravelly voice, Lower East Side accent, and other factors all played into his ultimate fame.

Frank Sinatra and Jimmy Durante both appeared in the 1947 film, It Happened in Brooklyn and performed “It’s Gotta Come From The Heart.” That’s a historical moment.

For more Jimmy Durante, see “I’ll Be Seeing You,” “The Glory of Love,” and “I’ll See You in My Dreams.”

Vic Damone

One fateful day, American traditional pop and big band singer and actor Vic Damone ran into Perry Como at the Paramount Theater and sang for him. Como was impressed, and Damone landed an audition that would kick-start his career.

Vic Damone was effectively a contemporary of Frank Sinatra, counting him as his top influence. Sinatra would later comment that Vic had “the best set of pipes in the business.”

Listen to his “An Affair to Remember,” “Do I Love You,” “Smoke Gets in Your Eyes,” and “You Were Only Fooling.”

Jo Stafford

American traditional pop singer Jo Stafford had a prolific five-decade career spanning from the 1930s to the 1980s. Sinatra and Stafford’s paths would cross on many occasions, especially given her involvement with the Pied Pipers.

Have a listen to “No Other Love,” “Dream,” “You Belong To Me,” “Manhattan Serenade,” and “Shrimp Boats.”

Fred Astaire

Fred Astaire was many things – most notably one of the all-time greatest popular-music dancers. Over the course of 76 years, Astaire would dance, act, sing, and present, earning countless awards along the way.

You can’t go wrong with “Cheek to Cheek,” “Puttin’ On The Ritz,” “Top Hat White Tie And Tails,” and “Isn’t This a Lovely Day.”

Elvis Presley

Frank Sinatra once panned rock and roll as one of the worst things to ever happen to music.

Presley, however, would appear on The Frank Sinatra Timex Special in 1960. So, Sinatra must have revised his opinion of Elvis. That’s not surprising, considering The King's aptitude for singing ballads.

The two probably have more in common than either would like to think.

Singers Like Frank Sinatra, Final Thoughts

And so, we conclude another guide on singers who sound like each other. Who is your favorite? Did you learn something new? Is there anyone missing from this list?

We hope you had as much fun as we did.