As one of the most popular and influential singers, actors and personalities of the 20th century, Frank Sinatra was responsible for hits like My Way, Fly Me To The Moon, Theme From New York and of course, this one:
Starting his singing career as a teenager after hearing recordings of Bing Crosby, Sinatra first joined a local singing group called The Hoboken Four, who he would tour with for years until the group disbanded.
Following this stint, Frank Sinatra would sing alongside other famous musicians, including trumpeter Harry James and trombonist Tommy Dorsey. He made his solo debut in 1944 after signing with Columbia Records, and didn’t stop: over his career, he sold 150 million records, making him one of the best-selling artists of all time.
With a smooth crooner voice synonymous with the big-band era, Sinatra’s music inspired countless artists, both back in the day and now. If you’re after similar artists like Frank Sinatra, here are a few to add to your playlist.
Similar artists from Frank Sinatra’s era
Dean Martin was an American singer, actor, and comedian who was most well-known back in the day as one half of Martin and Lewis comedy duo. After splitting with Jerry Lewis, Dean Martin became a successful solo artist, putting out hits such as That’s Amore, Memories are Made of This and Everybody Loves Somebody (a Frank Sinatra cover).
With the same baritone sound as many other artists during the big-band era, Frank Sinatra and Dean Martin would regularly perform together in Las Vegas as part of the infamous Rat Pack duo. On top of being similar in sound, Dean Martin and Frank Sinatra actually performed many songs together, such as this one:
Sammy Davis Jr.
Another member of the Rat Pack, Sammy Davis Jr. was a singer, musician, dancer, and actor—as well as a vaudevillian, activist, and comedian. He starred in Broadway productions of Mr. Wonderful and Golden Boy before appearing in the Rat Pack movie Ocean’s 11 (which also starred Frank Sinatra and Dean Martin).
Sammy Davis Jr.’s biggest hit was The Candy Man, which reached the top of the Billboard 100 in 1972.
While Sammy Davis Jr. was busy hosting his own show 1966, his career slowed in the late sixties and early seventies and he joined the rest of the Rat Pack in Las Vegas.
No list of artists like Frank Sinatra is complete without a mention of Bing Crosby, simply because Bing Crosby was the artist who inspired Frank Sinatra to sing.
Like Sinatra, Bing Crosby was a successful singer and actor during his time. He starred in Holiday Inn with Fred Astaire in 1942, while his recording of White Christmas ended up becoming one of the most popular songs of the entire century.
Most famously, music critic Henry Pleasants described Bing Crosby’s music as conversational and intimate, and was one of the first to coin the term “crooner”. This phrase ended up being used to not only describe Bing Crosby, but also Frank Sinatra, Dean Martin, Sammy Davis Jr. and many in the Rat Pack.
Contemporary artists inspired by Frank Sinatra
Loved around the world, Michael Buble is a Canadian singer and songwriter who found global success with his albums It’s Time and Call Me Irresponsible.
With a music style best described as easy listening, Buble combines influences from traditional pop, pop rock, jazz, show tunes, swing, blue-eyed soul and big band in songs like this one:
And this one:
Buble himself has also admitted that Sinatra had a heavy influence on his music. In an interview with CNN, he said, “I would love to sound like Frank Sinatra. I think that he’s one of the greatest vocalists that ever lived. And you know, I work very hard at stealing from him and people like Tony Bennett and Ella Fitzgerald and Sarah Vaughn to find my own sound… I tried to become the healthy combination of all my idols.”
Harry Connick Jr.
Born in New Orleans, Louisiana, Harry Connick Jr. was a musical prodigy by age 10 and has sold over 28 million records worldwide to date.
A singer, composer, actor and TV host, Harry Connick Jr. earned a Grammy for his work on the soundtrack of the film When Harry Met Sally, which went double platinum (no doubt thanks to this song below):
After this, his career took off: He began touring the world, and released several hit songs, from originals like One Fine Day to Sinatra covers like The Way You Look Tonight. Oozing the sound of New Orleans, Harry Connick Jr.’s crooning big-band style is clearly influenced by Sinatra, and he remains one of the few modern artists still making music in that genre.
Reinterpreting Sinatra for the ages
While there aren’t that many crooners left, there are plenty of artists still paying tribute to Sinatra in their own way—and reinterpreting his sound for the modern era.
Sid Vicious, Jawbox, Cake, Iggy Pop, They Might be Giants, She & Him and Maroon 5 have all covered Frank Sinatra songs, including one of our favourites:
Meanwhile, musical legends such as Willie Nelson and Bob Dylan both have entire albums made up of only Frank Sinatra songs.
All of these prove that, more than half a century on, Frank Sinatra is still one of the greatest singers of all time, and his influence is woven into the fabric of music made around the world.