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25 Singers Similar to Frank Sinatra

25 Singers Similar to Frank Sinatra

Francis Albert Sinatra is the full name of “Ol’ Blue Eyes” himself, Frank Sinatra. He dazzled his way into the music scene in the mid-1930s, and in 1943, he made his debut acting career which both went on to achieve remarkable success. Frank Sinatra won multiple awards, such as nine Oscars and a Grammy; he is also considered the best singer of the 20th century.

Sadly, Sinatra died of a heart attack in 1998, but his music and legacy continue to thrive up to this present day.

“Classic pop,” big band, jazz, “easy listening,” and swing best describe Frank Sinatra’s genre of music. He compiled eight compilation albums, had fifty-nine studio albums, and released two live albums in his lifetime. Research shows, Sinatra has successfully sold over 150 million albums worldwide.

As you can see, we are still craving ‘The Voice’, fellow Sinatra fans! But don’t you worry, because we have twenty-five singers similar to Frank Sinatra that you will ‘find all so amusing.’ Let us take a Sinatra-fueled journey together and discover artists of the past and contemporary artists you need to be adding to your playlist.

Artists of the past:

1. Bing Crosby

Very Best of

We begin the list with Frank Sinatra’s music inspiration: Bing Crosby. Bing’s picture is said to have been on Frank Sinatra’s wall as a teenager. Without him, we may never have come across Frank or this article so, thank you, Bing!

Harry Lillis Crosby, better known as ‘Bing Crosby’, was an American actor and singer from 1931 to 1977 when he passed away. What comes to mind when thinking of his musical genre is crooner-style ‘traditional pop’ and country. He achieved a Guinness world record for the most successful Christmas song of all time, White Christmas.

 Crosby has sold over 40 million copies, won multiple awards, released 324 albums, and today he has almost close to one billion sales in his music alone-WOW.

Having performed various iconic duets together, including White Christmas (Happy Holidays), both Crosby and Sinatra were fans of each other’s work. YouTube is full of their duets; you need to go and search them!

2. Dean Martin

Kiss Me Stupid Dean Martin 1964 Photo Print (8 x 10)

In 1932 Italian-American Dino Paul Crocetti became Dean Martin, the star actor, singer, comedian, rat pack member, and television personality. Martin’s music includes jazz, ‘traditional pop,’ easy listening, swing, and country. With over 3412 appearances, 66 albums, over 620 compilations, and hundreds of awards to his name, including a Golden Globe and a Grammy, it is no wonder he was known as “the king of cool!”

Dean and Frank were like brothers to each other, even raising their families together, ‘That’s Amore!’ If you have not seen ‘Christmas with the Martins and Sinatras,’ you seriously need to! This duo shared many fun times in the Rat Pack, music duets, and starred in eight movies.

Sinatra and Martin both shared that classic and iconic silky-voiced crooner sound. If you are a fan of Frank Sinatra, dress up in a suit and grasp the nostalgia because you will love Dean Martin!

3. Nat King Cole

Ultimate Nat King Cole [2 LP]

Nathaniel Adams Coles, better known as Nat King Cole, was an American singer, songwriter, actor, jazz pianist, and all-rounder! From 1935 until his unfortunate passing in 1965, he enchanted us with his voice. The music genre of Nat King Cole is easy listening, jazz, and ‘traditional pop.’

He enjoyed tremendous success with his career spanning over 134 albums, an award-winning trio (The Nat King Cole Trio), sold over 50 million records, and achieved one hundred top hits. There is nothing quite like Nat King Cole’s incandescent voice!

Sinatra once told a reporter that he puts Nat’s record on whenever he gets home and wants a little relaxation. ‘Traditional pop’ is a style they both sing in and share that lustrous crooner voice we cannot resist! Fans of Sinatra, you will be captivated by Nat King Cole’s music because he is truly ‘unforgettable.’

4. Sammy Davis, Jr.

Seven Classic Albums

In addition to being a member of the Rat Pack, Sammy Davis Jr. was a comedian, actor, dancer, entertainer, and singer from the age of seven in 1933 until he, unfortunately, passed away in 1990 due to throat cancer. Dubbed as ‘The greatest entertainer in the world,’ it is no wonder he was known as ‘Mr. Show business.’  

For generations, Mr. Davis’s voice has melted our hearts, singing in various genres; jazz, ‘traditional pop,’ and rock. He released 93 albums and made over $50 million in his singing career alone.

As well as being lifelong friends, Sinatra and Davis worked together for many years. Their musical styles are highly similar as they both evolved during an era defined by glitz and glamour. So, Sinatra fans, get ready because Sammy offers your musical interests a wide array of music that you will love!

5. Perry Como

The Very Best Of Perry Como

Italian American singer, actor, and television personality Perry Como made his career debut in 1932 with a remarkable six centuries’ worth of entertainment; he retired in 1997 but unfortunately passed away from Alzheimer’s disease in 2001.  His genre is of music is best described as rock, country, ‘traditional pop’ and easy listening.

In his time of ‘show biz,’ he released 66 albums that achieved ENORMOUS success, and to date, he sold over 100 million records! He won a multitude of awards, including five Emmy Awards and a lifetime achievement award.

Did you know there was an offer for him to be a Frank Sinatra imitator? Talk about being Similar to Frank! Your Sinatra’ musical taste buds’ are probably craving to hear some of ‘Mr. Class’s’ music.  We suggest you welcome Perry by listening to classics like It’s Impossible and You Can’t Pull the Wool Over My Eyes.

6. Ella Fitzgerald

Ella Fitzgerald: A Biography Of The First Lady Of Jazz

As a jazz singer with a pure voice, Ella Fitzgerald (1917-1996) was the most famous jazz singer for many decades, starting in 1938 at just 21 years of age. With over 200 albums, thirteen Grammy Awards, and over 40 million records sold, it is no surprise she is known as the ‘queen of jazz.’

Sinatra had great respect for Ella and performed many duets together. “The best way to start any musical evening is with this girl. It doesn’t get better than this,” said Sinatra before their iconic The Lady Is a Tramp duet.

Their voices and duets blended well together because they sang in similar styles that complemented each other perfectly. You need to listen to Ella’s music and many iconic duets with Frank because you will find yourself lost in her music as a Sinatra fan.

7. Bobby Darin   

Bobby Darin - Legends in Concert

In the late 1950s, American singer, songwriter, impressionist, cabaret performer, comedian, and actor Bobby Darin (1936-1973) made his mark in the music scene with his number 1 hit,” Splish Splash.” The multi-talented two-time Grammy Award-winning Darin was known for his jazz, country, rock folk, swing, and country music.

Bobby Darin released 46 albums and had various number one hits. Unfortunately, he only lived to the age of 37 but wildly succeeded in the short time he was alive.  He indeed was a multi-talented artist.

Frank Sinatra inspired Bobby Darin, but they had a bit of a rocky relationship because Darin said in an interview, he wanted to surpass everything Sinatra has done; despite this, Sinatra recognized his talent. Frank even covered Bobby’s famous hit Mack the Knife. So put on Bobby Darin’s greatest hits because you will surely enjoy his music!

8. Rosemary Clooney

Girl Singer: An Autobiography

In 1950, the world was introduced to pop and jazz singer Rosemary Clooney (1928-2002). Her velvety and warm voice enchanted many. She celebrated significant success with 87 albums, a net worth of $20 million, multiple nominations, and awards.

There was a special magical connection between Sinatra and Clooney on stage. As they sang Peachtree Street together, they incorporated jazz wonderfully. Listen to Rosemary Clooney, and she will captivate you with her voice, just like Frank Sinatra was.

9. Keely Smith

I Wish You Love - The Very Best Of Keely Smith 1956-1959 [ORIGINAL RECORDINGS REMASTERED]

In 1949, Las Vegas legend, American jazz and pop music singer Keely Smith (1928-2017) made her debut singing career in Hollywood. Keely was one of the most popular singers of her time, having won multiple awards, including the first-ever Grammy Award for best performance by a group or duo.

Smith released twenty-eight albums in her time and accumulated a net worth of over $6 million before she passed away. Did you know Frank Sinatra had his record label called Reprise Records? In 1957 she signed with the brand and saw significant success.

Sinatra highly influenced Smith, they performed many duets together, and in 2001 she released a Grammy-nominated album called Keely Sings Sinatra.  The pals of the Rat Pack even named her the “female Sinatra.” So, “Hey, Boy! Hey, Girl!” Keely Smith needs to be on your playlist!

*FUN FACT- Frank and Keely were romantically involved! While she was married to Louis Prima, Smith had a love affair with Sinatra, and he even asked her to marry her. She declined, but her tribute album for Sinatra was taking the meaning of loving and honoring him seriously.*

10. Paul Anka                 

Singing & Swinging - The First Three Albums Plus Bonus Tracks [ORIGINAL RECORDINGS REMASTERED] 2CD SET

In 1957, teen idol, singer, and songwriter Paul Anka made a massive splash into the music scene with his blend of easy listening, pop, jazz, and rock. Since then, Anka has won many awards, has made over 120 albums, and has sold over 10 million albums worldwide. His music continues to trend on major social media platforms like TikTok.

Did you know that he wrote the infamous song My Way for Frank Sinatra? That alone is an achievement. To think of the countless number of times it has been covered would be exhausting!

His biggest musical inspiration and close friend was Frank Sinatra, who influenced his style of music. He even sang with the Rat Pack and performed, and later after Sinatra’s death, he paid tribute to Sinatra, performing My Way with Frank Sinatra’s voice in the background. Bring Paul Anka into your musical life; you will not regret it!

11. Julie London

Ultimate Collection

That sensual and sultry voice of American jazz/pop singer and actress Julie London (1926-2000) is something that swoons you away. Julie’s singing career began in 1955 with Liberty records that she helped establish; her nickname was ‘Liberty Girl’ because she saw tremendous success with the label.

She released 32 albums and sold millions of records. Her biggest single ever, Cry Me A River, sold over 3 million copies alone. It is no wonder Billboard Magazine named her the most popular female artist from 1955-1957.

Frank Sinatra and Julie London are similar because they both come from that same classy Hollywood era. The two were friends and great fans of each other; London has even covered Sinatra songs like My Kind of Town and Fly Me to the Moon. We suggest you search Julie London’s greatest hits on YouTube or Spotify; get ready to be dazzled by the charm and elegance of Julie’s voice.

12. Dick Haymes

The Best of Dick Haymes 2 Lp

In the late 40s and early 50s, Argentinian-American pop singer and actor Dick Haymes (1918-1980) became one the biggest stars. He released sixty albums, was awarded two stars on The Hollywood Walk Of Fame, and achieved a net worth of $8 million.

He replaced Frank Sinatra twice; in the Harry James Orchestra and Tommy Dorsey Orchestra. The two worked closely together for many years and, it is often noted how similar they were to each other.  We suggest you listen to Mr. Haymes as his voice will undoubtedly memorize you!

13. Tony Bennett

All Time Greatest Hits

For two centuries, Tony Bennett has swooned us away with his beautiful crooner voice. He has sung in many genres, but he is most known for being jazz and “traditional pop” singer. With 18 Grammy Awards, 10 million record sales in the last ten years, and seven decades’ worth of albums, to say he has had a BOOMING career would be an understatement.

Tony Bennett has raved about the love Frank Sinatra and himself had for each other for many years. They both sing in similar tones and styles that are magnificent. We suggest you listen to Tony Bennet Jazz album and his duets with Frank Sinatra, but you have seven decades to choose from Tony!

In 2021, due to Alzheimer’s disease, Tony retired from music at the age of 95; we wish Mr. Bennett all the best and commend him for his many years of work.

14. Vic Damone

Hits Collection 1947-62

Since the 1940s, American actor, television presenter, big band, and traditional pop singer Vic Damone (1928-2018) succeeded as a highly talented man with many talents. He achieved a multitude of top hits, 88 albums, and millions of record sales.

When Frank Sinatra says you have ‘the best pipes’ in the business, you know you are talented! They both shared that beautiful baritone-style voices. Take Frank’s word for it and discover why Frank Sinatra loved Damone’s voice so much!

15. Peggy Lee

Fever: The Very Best Of Peggy Lee

American popular music and jazz singer Peggy Lee (1920-2002) has quietly captivated the world with her beautiful voice for over seven decades. Peggy was a singer, actress, singer, and songwriter who recorded 88 albums, sold millions of records and won many awards, including a Grammy.

“The female Sinatra” is what Tony Bennett called her because she had an incredible voice. She did things like Sinatra, ‘her way’ by helping to create every aspect behind her music. This female crooner is undoubtedly worth a listen!

Contemporary Artists:

16. Michael Bublé

To Be Loved

Influenced by Frank Sinatra, Four-time Grammy Award-winning Canadian songwriter, singer, and record producer Michael Bublé is a popular and successful modern-day crooner. In 1987, the British Columbia Youth Talent Competition launched his career, and the rest is history!

He has released fourteen albums, has achieved many number 1 hit, and has sold over 75 million records worldwide. Known for his jazz and soul sound, Bublé keeps the ‘Sinatra sound alive.’  His voice and style are indeed a class act and are highly like Frank Sinatra.

Do not get us wrong, Bublé is not a Sinatra imitator; he developed his unique sound with a ‘Sinatra twist.’ His music is breathtaking, from Michael Bublé Christmas Album to his iconic Frank Sinatra covers. Sinatra fans, you will LOVE Michael Bublé’s music!

17. Sal Valentinetti

"The Voice"

The fifth-place winner of America’s Got Talent 2016 and golden buzzer act, American-Italian, Sal’ The Voice’ Valentinetti, dazzled our hearts with his charm, old soul, and silky classic-sounding voice since the early age of 20.

He took our breath away with his striking and almost identical cover of Frank Sinatra’s My Way in his2016 AGT audition. He has released two albums, a cover EP titled The Voice with covers dedicated to Frank Sinatra’s greatest hits, and has continued to sell out shows all over America.

His latest 2021 album Little Valentine is marvelous that Sinatra fans will love. Close your eyes and let ‘The Voice’ sweep you off your feet.

18. Diana Krall

Wallflower (Deluxe Edition)

Canadian jazz singer Diana Krall is known for her sultry and beautiful contralto voice. She has released 22 albums and sold over 15 million albums worldwide. This two-time Grammy Award winner is one of the most popular female jazz artists of our time.

She made our list because her traditional pop and jazz sound is similar to what we love about Sinatra and his time. Fans of Frank Sinatra will love Diana Krall’s voice and highly enjoy her Sinatra covers. So sit back and let Diana’s voice take you to a beautiful, magical musical world!

19. Landau Eugene Murphey, Jr.

That's Life

A humble jazz singer and winner of America’s Got Talent 2011, Landau is known for:  his charming charisma, beautiful classic-sounding voice, jazz musical style, and singing the Sinatra classics magnificently.

His story is one of ‘from rags to riches’ which he wrote a book called From Washing Cars to Hollywood Star, which then became an Amazon #1 bestseller. Since then, Landau has released two studio albums, one cover album of Sinatra and Dean Martin classics, and has toured worldwide.

Frank Sinatra lovers, be ready to become a Landau lover too because you will fall head over heels in love with his voice!

20. Matt Dusk

Two Shots

After completing an honors degree in music, Matt Dusk started releasing individual CDs and then, in 2004, landed a major record deal with DECCA Records. With fourteen albums which three were awarded GOLD, over one million albums sold, a devout fan base, and three number one radio hits, Matt Dusk is somebody you NEED to know!

Dusk has a beautiful modern crooner-style singing voice and is known for his jazz and popular music style. Matt’s voice is so beautiful and similar to Sinatra; it is almost as if Frank himself came to sing for him! We recommend you listen to Dusks cover album called Sinatra and JettSetJazz. ENJOY!

21. Dennis Van Aarssen

Forever You

Dennis Van Aarsen is the jazz singer and winner of The Voice 2019 Holland; you need to know about him! When I listen to his voice, it is as if I am listening to something from the ’50s.

He received an Edison Jazz Award, made an album called Forever You, and has millions of views on YouTube. Sinatra fans, you will love his “Ol’ Blue Eyes” covers and sound!

22. Harry Connick, Jr.

Your Songs

Three-time Grammy Award-winning singer, TV host, composer, and actor Harry Connick, Jr. began his career in 1987 and has received significant success since then.  He has made and appeared in 38 albums and successfully sold over $28 million in record sales alone.

If you love jazz, big-band, funk, and romantic ballads, then Harry Connick, Jr. Is the man for you! Frank Sinatra has always been a big inspiration to Harry, covering famous songs on tour like The Way You Look Tonight; he is still one of the few modern artists with that ‘old school sound.’

You will love his music, especially these albums: iconic and award-winning When Harry Met Sally soundtrack, True Love: A Celebration of Cole Porter, and We Are in Love. Sinatra fans, get ready because you are about to be swept away by the fantastic smooth voice of Harry Connick, Jr.

23. Richard Cheese & Lounge Against the Machine

Lounge Against The Machine by Richard Cheese (2000-05-03)

Since 2000, Mark Jonathan David(vocals), Bobby Ricotta(pianist), Billy Bleu(bass), and Frank Feta(drums) have been a part of this lounge-sounding, jazz, and retro-inspired modern-day quartet. They have released 29 albums, appeared in many famous movie soundtracks such as Dawn of the Dead, been on tour to many different countries, and have sold more than 250 000 CDs alone.

Imagine Frank Sinatra singing Guns n Roses Welcome to the Jungle; I cannot! But this sums up what Richard Cheese and Lounge Against the Machine music is all about. Dean Martin and Frank Sinatra influenced their passion to ‘retrofy’ modern music hits.

Add a bit of swing to your playlist because you cannot get more ‘modern Sinatra’ than this band. I am sure your inner love for Sinatra is craving to listen to their music, so YouTube, Spotify, and iTunes are places for you to find them. Start spreading the news because this band will make you feel like you are in a classy lounge in old New York!

24. Brendon Urie

Panic! at The Disco -Brendon Urie Music Poster - 24" x 36"

As the frontman of Panic! At the Disco, Brendon Urie is a modern-day music icon. He has sung in a variety of different genre styles, but today, we are focusing on his jazz style of music. Since the start of Urie’s career in 2004, he has become a global phenomenon.

He regularly sings Frank Sinatra covers, and at the AMPAS’s 2014, he dedicated a whole live performance to him. Brendon Urie credits Sinatra’s music as the soundtrack of his life. You NEED to listen to his Sinatra-style songs like Death of a Bachelor and his cover songs.

25. Seth McFarlane

No One Ever Tells You

Finally, last but certainly not least, Seth McFarlane. Not many people know, but this comedian, impressionist, actor, producer, and screenwriter is a fantastic singer and Grammy-nominated vocalist too! He received singing lessons from Sally and Lee Sweetland, who trained Frank Sinatra too!

Seth McFarlane saw Sinatra as an inspiration that influenced his classical musical jazz style, of which he has made six albums in total. In the animated movie Sing, he plays the voice of the character Mike where he sings Sinatra classics like My Way and Pennies from Heaven. Seth has a truly ‘out of this lifetime’ voice.

He is undoubtedly a ‘man of many talents!’ We suggest you listen to any of his albums IMMEDIATELY as they will teleport you to the swinging Sinatra era we all know and love.

So, Frank Sinatra fans, our journey has ended, but we hope you will LOVE and get to know all the artists mentioned on this list. Happy listening!


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