19 Best Singers Like Frank Sinatra

Frank Sinatra was one of the most influential singers of all time. But as they say, rising tides raise all ships, and Sinatra was surrounded by incredible talent – influences, peers, and contemporaries alike, many of whom became unmistakable legends in their own right.

The question isn’t necessarily who can sing like Frank Sinatra. The question is more so who he was influenced by, and who was influenced by him.

In this guide, you will discover the best singers like Frank Sinatra.

Dean Martin

Strange to think, but American singer, actor, and comedian Dean Martin’s influence is often underestimated. Even Elvis “The King” Presley was said to have learned a thing or two from Martin’s vocal style, and guess what? Martin was even good friends with Frank Sinatra and Sammy Davis Jr.

The Martin-Sinatra connection is well known, however, and the two would act together, share stages, and even form the Rat Pack, along with Joey Bishop, Sammy Davis Jr., and Peter Lawford.

Some classic Dean Martin moments include “Everybody Loves Somebody,” “On An Evening In Roma,” and “Ain’t That a Kick in the Head.”

Nat King Cole

American singer, jazz pianist, and actor Nathaniel Adams Coles aka Nat King Cole found mainstream success in the 1950s, a time when racial discrimination was still prevalent.

All sources seem to indicate, however, that Frank Sinatra was kind to Cole as well as African Americans in general.

Cole was a part of the Metronome All-Stars in 1946 and 1947, and he was the pianist on Frank Sinatra’s “Sweet Lorraine.”

Nat King Cole is remembered well for his “Unforgettable,” “Smile,” “Mona Lisa,” “Autumn Leaves,” “Stardust,” and many others.

Tony Bennett

Retired American singer Tony Bennett is a traditional pop standard, show tune, big band, and jazz legend. In 1965, Frank Sinatra even called Tony Bennett “the best singer in the business.” Bennett, now 96, also attended Sinatra’s funeral in 1998 and was even on the short list of people who addressed attendees.

Bennett obviously held Sinatra in high regard as well, releasing a tribute to him called Perfectly Frank in 1992.

Bennett has no shortage of material, but some good tunes to check out are “Rags to Riches,” “New York State of Mind,” “Body and Soul,” “Love for Sale,” “The Very Thought of You,” and “For Once in My Life.”

Bing Crosby

American singer and actor Bing Crosby is considered the first multimedia star. Frank Sinatra loved Bing’s easy, intimate vocal style and was greatly influenced by it. Apparently, he even idolized Bing.

Sinatra and Crosby even got to collaborate on America, I Hear You Singing, a tribute to President John F. Kennedy, alongside Fred Waring. The two would also act together in High Society in 1956.

In addition to Frank Sinatra, Bing Crosby was a huge influence on Dean Martin, Perry Como, Elvis Presley, John Lennon, Dick Haymes, and doubtless many others.

Sammy Davis Jr.

American Renaissance man Sammy Davis Jr. began performing in Vaudeville at the tender age of three. Whether as a singer, actor, dancer, comedian, TV director, or film producer, Sammy Davis Jr. left an indelible mark on this world before passing at the age of 64 in 1990.

Sammy Davis Jr. toured widely with Frank Sinatra, Dean Martin, and Liza Minnelli. Of course, he was one of the key players in the Rat Pack as well.

If you haven’t heard them already, you’ll certainly want to check out “The Candy Man,” “I’ve Gotta Be Me,” “Mr. Bojangles,” “Hey There,” and “Me and My Shadow.”

Perry Como

American singer, actor, and TV personality Perry Como had a professional career spanning over 50 years. Like Sinatra, Como was very much influenced by Bing Crosby and his singing style. Como would tend towards vocal pop recordings throughout his prolific career.

At one point, Como was even approached with the idea of becoming a Frank Sinatra imitator, something he probably could have pulled off. Ultimately, he went his own way.

Sinatra and Como would perform together in 1982 at Italian President Sandro Pertini’s White House state dinner.

If you want to revisit his magic moments, listen to “And I Love You So,” “Magic Moments,” “For the Good Times,” “Papa Loves Mambo,” and “It’s Impossible.”

Bobby Darin

American musician and actor Bobby Darin started out as a songwriter for pop singer and actress Connie Francis. His personal breakthrough success would come in 1958 with a song all kids should know – “Splish Splash.”

Frank Sinatra reportedly had respect and admiration for Bobby Darin and his obvious talent, though some have theorized that Sinatra may have been threatened by him too.

Some recommended listening includes “Call Me Irresponsible,” “Beyond the Sea,” “Mack the Knife,” “Queen of the Hop,” and “Dream Lover.”

Johnny Mathis

American singer Johnny Mathis counted Bing Crosby, Nat King Cole, and Lena Horne among some of his chief influences. Does that sound like someone else you might know?

Mathis is considered the third best-selling artist of the 20th century, with dozens of albums achieving gold or platinum status.

With Sinatra and Mathis taking after Crosby, it’s clear they are cut from the same cloth.

“It’s Not for Me to Say,” “Misty,” “Wonderful! Wonderful!,” “My Love for You,” and “What Will My Mary Say” are some good places to start with Mathis’ expansive catalog.

Mel Tormé

Mel “The Velvet Fog” Tormé, much like Sammy Davis Jr., was a bit of a Renaissance man, finding success as a musician, singer, drummer, actor, author, and more.

As an actor, Tormé made his debut in Frank Sinatra’s Higher and Higher, and when he formed Mel Tormé and His Mel-Tones in 1944, he patterned his band after Frank Sinatra and The Pied Pipers.

Tormé’s hits include “Comin’ Home Baby,” “That’s All,” “I’ve Got You Under My Skin,” “Blue Moon,” and “Too Close for Comfort.”

Michael Bublé

For kids who might mistake Michael Bublé as one of a kind, he credits Frank Sinatra, Dean Martin, Tony Bennett, Elvis Presley, Sam Cooke, and Bobby Darin as his primary influences.

The Canadian singer, in fact, has been informally credited with helping revive interest in the Great American Songbook and traditional pop standards.

Some solid contributions via Bublé include “Feeling Good,” “Sway,” “Home,” “It’s a Beautiful Day,” and “Haven’t Met You Yet.”

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.