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31 Best Songs From 1944

There were so many wonderful tracks that came out in 1944, but do you know what makes the top of the list? Continue reading as we go over our list of the 31 best songs from 1944, and check them out, as you might want to add them to your playlist! 

1. I Wonder – Private Cecil Gant 

First on our list is Private Cecil Gant with I Wonder, and this song hit number one on the JukeBox Race Records chart. It would be the biggest hit that he would have in his career and is one of the biggest tracks of 1944.

He was an African American man who had served in World War II, and this track is all about the uncertainty surrounding being apart from your loved ones while serving the country. It’s also a song that still resonates with soldiers even today. 

2. Straighten Up and Fly Right – King Cole Trio

Straighten Up And Fly Right

Next up is the song Straighten Up And Fly Right by the King Cole Trio, and this song hit number nine on the Billboard Pop chart and one on the Harlem Hit Parade chart. It stayed on the Hit Parade chart for over 10 weeks nonconsecutively in the number one position. It also made it to number one on the Most Played JukeBox Hillbilly Records chart and stayed there for six weeks nonconsecutively.

In the track, you can distinctly hear Nat King Cole’s soulful and powerful vocals while the trio provides amazing harmonies to make the song memorable. It’s no surprise that this was their most popular and successful tune. 

3. I’ll Be Seeing You – Tommy Dorsey And Frank Sinatra 

I'll Be Seeing You

Frank Sinatra had a hit with I’ll Be Seeing You, which featured Tommy Dorsey. This version was a smash hit peaking at number four while Bing Crosby’s original version hit number one that same year. If you’ve ever missed a loved one, then this song is going to resonate with you since it’s all about missing someone you love. 

4. Till Then – The Mills Brothers 

Till Then (1958 Version)

The Mills Brothers are on the list with Till Then, which went to number eight on the Billboard Best Seller chart. It went to number one on the R&B charts, and it is a song that’s all about having a future with someone and experiencing ever-lasting love. This is a romantic track that has a very slow melody, and it’s a timeless love song that has been covered multiple times through the years

5. G.I. Jive – Louis Jordan 

Louis Jordan & His Tympany Five - GI Jive (Live)

Next up is a song that dealt with what the soldiers’ lives were like during World War II, and it’s called G.I. Jive, which had been covered by Louis Jordan a few months after its initial release by Johnny Mercer. The soldiers liked this track and so did everyone else, which is why it went to number one on the Billboard Pop chart as well as the Harlem Hit Parade. 

6. Into Each Life Some Rain Must Fall – Ella Fitzgerald And The Ink Spots 

Into Each Life Some Rain Must Fall

Attention all fans of the documentary Why We Fight, Ella Fitzgerald and The Ink Spots had a hit with Into Each Life Some Rain Must Fall, and this song was featured in it. This was a track that is about having hope and keeping faith during times of trouble or hardship. It’s one of the most uplifting songs on our list, and it went to number one on the Billboard Pop and Harlem Hit Parade charts. 

7. You Always Hurt The One You Love – The Mills Brothers 

You Always Hurt The One You Love (1958 Version)

You Always Hurt The One You Love was a hit for The Mills Brothers, and it went to number one on the Billboard charts. This song explores the concept that even if you don’t mean to hurt someone that you love, you unintentionally still can, and it goes into these thoughts about love and how hurting is always a part of love. 

8. I Love You – Bing Crosby 

Next up is Bing Crosby with I Love You, which was perfect for him because of his powerful and smooth vocals that made the sentiment of saying I love you even more significant. This track was a huge hit and it’s one of his most romantic and heartfelt songs.

9. I’m Beginning To See The Light – Harry James and His Orchestra 

I'm Beginning To See The Light

On the list next is Harry James And His Orchestra with I’m Beginning To See The Light, which went to number one on the Billboard chart and stayed there for two weeks. This song is about how when you fall in love, everything else will begin to fall into place and make sense to you. This is one of the jazz standards that has an upbeat melody and is perfect for describing what it’s like to fall in love. 

10. Swinging On A Star – Bing Crosby 

Swingin' On A Star

Calling all fans of the movie Going My Way, Bing Crosby had a hit when he released Swinging On A Star, which can be found in this film, and it even won Best Original Song at the Academy Awards. This hit number one on the charts, and it’s all about how you should go for your dreams, and it’s a catchy upbeat tune about following whatever path in life you want. 

11. I’m Making Believe – Ella Fitzgerald And The Ink Spots 

Ella Fitzgerald and The Ink Spots are on the list again with I’m Making Believe, which hit the top of the Billboard Best Selling Retail Records chart and stayed there for two weeks. This song has sold more than one million copies and was also number three on the Most Played JukeBox Records chart. The track is still a popular and beloved song to this day, and it’s one of those tracks that you’ll want to play over and over. 

12. Pretty Kitty Blue Eyes – The Merry Macs 

Pretty Kitty Blue Eyes

The Merry Macs is on the list with Pretty Kitty Blue Eyes. It is about a woman with blue eyes like a pretty kitty, which means it’s a deep and beautiful blue color. The song is very catchy, memorable, and playful, and it’s sweet when you think about the comparison of the woman to the cat.

13. I’m Lost – Benny Carter

On the list now is Benny Carter with the song I’m Lost, which went to number one on the Harlem Hit Parade chart and was the most successful version of this song. It’s all about feeling lost and alone and feeling uneasy and uncertain of the future. If you’ve ever felt alone then you’ll understand and feel the lyrics, and this track is one of the best jazz songs of the decade. 

14. The Patty Cake Man – Ella Mae Morse 

The Patty Cake Man

Ella Mae Morse makes our list with The Patty Cake Man, which is a song you probably know from being a kid and playing Patty Cake (apparently, the game’s called Pat-A-Cake) with your friends. The track is playful and joyful and will bring a smile to your face as it talks about a guy who goes around the neighborhood making cakes for kids. 

15. And Her Tears Flowed Like Wine – Stan Kenton Feat. Anita O’Day 

And Her Tears Flowed Like Wine

On the list next is Stan Kenton and Anita O’Day with their jazz song And Her Tears Flowed Like Wine, which is all about a woman who is crushed after learning her man cheated on her. You can feel the emotions in her voice, and it’s such a powerful track and relatable song to those that have been cheated on or betrayed in another way by their significant other. 

16. I Couldn’t Sleep A Wink Last Night – Frank Sinatra 

I Couldn't Sleep A Wink Last Night (1999 Remastered)

Frank Sinatra makes the list with I Couldn’t Sleep A Wink Last Night, which is all about a guy who stays up all night thinking of the woman he has fallen in love with. When you hear him sing this song, it’s easy to feel the depth of the emotions and feelings because his voice is perfect for this type of track. When you are in love with someone, you know how it can be hard to focus on anyone or anything else but them. 

17. Lili Marlene – Perry Como 

Perry Como was so popular in the 40s, and he had a hit in 1944 with Lili Marlene, which is one of those romantic songs where a soldier is spending time thinking about his significant other back home. There are a lot of emotions in this track, and it’s very sweet so it’s a song that not only was popular during World War II times but also just as popular and relevant today. 

18. Don’t Believe Everything You Dream – The Ink Spots

The Ink Spots - Don't Believe Everything You Dream 1944

Up next is The Ink Spots with Don’t Believe Everything You Dream, which is all about how you should be careful when you let your imagination get crazy and think too weird thoughts. While you can dream, it’s important to not let your mind wander in bad directions, and it’s a song that has remained a classic to this day. 

19. There’s A New Moon Over My Shoulder – Jimmie Davis

There's A New Moon Over My Shoulder

Next up is Jimmie Davis with the song There’s A New Moon Over My Shoulder, which went to number one on the Folk JukeBox chart for one week and stayed on the chart for 18 weeks combined. It’s a track about a guy who is going to start his life over and leave everything behind, so you can feel the freedom and personality in this song when he talks about beginning a new life. 

20. It’s Only a Paper Moon – King Cole Trio 

It's Only A Paper Moon (1956 Version)

The King Cole Trio is next with It’s Only A Paper Moon, which is about how your imagination is important for allowing you to create beautiful things. It’s whimsical and a classic track about how powerful using your imagination can be to create your own lovely world. Whether you’re younger or older, you’ll be able to relate to this song and how you can use your imagination to make yourself happy and daydream of all of the wonders and beauty that nature has to offer. 

21. The Music Stopped – Woody Herman 

Woody Herman - The Music Stopped

Woody Herman is on the list with The Music Stopped, which is all about when a relationship ends. It uses a lot of metaphors in the song to talk about its ending but you are still continuing on with your life. This is a beloved track people love to listen to because loss and heartache are feelings we all experience. 

22. Good Night, Wherever You Are – Russ Morgan 

Good Night, Wherever You Are

Next up is a World War II song called Good Night, Wherever You Are by Russ Morgan. This track is all about the soldiers fighting the war missing their family and friends, and it’s a very emotional and powerful song.

Since war is still something we face, it has become a track people turn to for comfort and support. Even people who don’t have loved ones fighting a war will enjoy this song because it’s also a good track if you’ve lost a friend or family member and are grieving that loss. 

23. Salty Papa Blues – Dinah Washington 

Dinah Washington is on our list with Salty Papa Blues, which is a timeless song about a woman who is exhausted from her man cheating on him. She tells him she is going to leave if he keeps it up, and this is one of those classic tracks about being fed up with a cheating lover, so it continues to stay relevant to this day. 

24. Artistry In Rhythm – Stan Kenton 

Artistry In Rhythm

Stan Kenton makes the list with the iconic jazz song Artistry In Rhythm, which includes all kinds of instruments such as percussion. It’s an energetic track that gives you the feel of what life was like in the 40s as it was one of the biggest jazz hits of that decade. 

25. His Rocking Horse Ran Away – Betty Hutton 

His Rocking Horse Ran Away

A song full of puns and all about learning how to grow up is next, which is His Rocking Horse Ran Away by Betty Hutton. The track is very fun and playful, and it’s one of those light songs that you can listen to and just feel nostalgic and happy.

26. By The River Of The Roses – Woody Herman 

Woody Herman - By The River Of Roses

Woody Herman makes the list with By The River Of The Roses, which is about how beautiful nature and roses are, including the river where you can hear the birds and see blooming flowers. The song includes saxophone, and it’s one of those whimsical pretty tracks that helps convey the thoughts of beauty and Mother Nature. 

27. When My Sugar Walks Down The Street – Ella Fitzgerald 

When My Sugar Walks Down The Street

Next is Ella Fitzgerald with the song When My Sugar Walks Down The Street. This track is all about how happy and excited she feels when she sees her significant other walking down the street, and it’s one of the most classic jazz songs of all time. 

28. Have Yourself a Merry Little Christmas – Judy Garland 

Have Yourself a Merry Little Christmas

Calling all fans of The Wizard Of Oz, Judy Garland had another hit song beyond the theme for that movie when she released Have Yourself A Merry Little Christmas. This track is one of the most common and famous Christmas songs. Reaching number 27 on the Billboard charts, it’s all about feeling hopeful during Christmas even if you’re going through hard times. 

29. Smoke On The Water – Red Foley 

Red Foley -- Smoke on the Water

Next on the list is Smoke On The Water, which was released by Red Foley, and it’s all about a guy on the run. The man was trying to get away from the cops and would use the smoke coming from a train as camouflage to hide. It’s one of the most famous country songs that has been covered by multiple artists ever since. 

30. I’ll Walk Alone – Dinah Shore 

I’ll Walk Alone is on the list which was most famously released by Dinah Shore. This song was for the movie Follow The Boys. It went to number one on the Billboard chart and 10 on the Harlem Hit Parade chart. This track is all about how a woman who is alone but is resilient and is going to stay strong. 

31. Try Me One More Time – Ernest Tubb 

Try Me One More Time

Last on the list is Ernest Tubb with Try Me One More Time, which is about a guy who’s asking his woman to give him another chance. This is an emotional song filled with honesty, and it’s also a very simple track that shines in the country blues genre to this day.

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