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.”