15 Best Songs From 1944

In 1944, iconic musicians such as Bing Crosby, Ella Fitzgerald, Judy Garland, and The Mills Brothers graced us with their enchanting voices and timeless melodies. Want to hear their hits? Well, here are the best songs from 1944.

“You Always Hurt The One You Love” by Mills Brothers

Song Year: 1944

One of the most popular songs from 1944 was “You Always Hurt The One You Love” by the Mills Brothers. This song was released in May 1944 on Decca Records and quickly became a hit among listeners.

The Mills Brothers were known for their signature four-part harmony sound, which made them stand out among other groups during that era. Their version of “You Always Hurt The One You Love” perfectly captures their unique style, with its catchy melody and heartfelt lyrics about love gone wrong.

“Trolley Song” by Judy Garland

Song Year: 1944

The “Trolley Song” is an unforgettable tune from the 1944 classic Hollywood film, “Meet Me in St. Louis.” Written by Hugh Martin and Ralph Blane, this iconic musical number was brilliantly performed by 17-year-old Judy Garland, who cemented her long-lasting legacy in cinema with her enchanting rendition of this song.

As one of four songs penned specifically for “Meet Me in St. Louis,” The Trolley Song perfectly encapsulates the charm and excitement experienced when riding a trolley through bustling city streets.

“Swinging On A Star” by Bing Crosby

Song Year: 1944

A timeless classic from the golden age of Hollywood, “Swinging On A Star” by Bing Crosby was one of the standout tunes from 1944. The song resonated with listeners due to its catchy melody and whimsical lyrics penned by Johnny Burke and composed by Jimmy Van Heusen.

In this legendary hit, Bing Crosby's smooth vocal stylings are accompanied by a pulsating big band arrangement conducted by John Scott Trotter. Known for its humorous animal references such as pigs and fish, “Swinging On A Star” showcases wordplay that elevates it into a shining example of popular culture during that era.

“I'll Walk Alone” by Dinah Shore

Song Year: 1944

“I'll Walk Alone” is a timeless classic ballad released in 1944 and performed by the legendary Dinah Shore. The song was written by renowned composers Jule Styne and Sammy Cahn, one of the most successful songwriting duos during the big band era.

The vocal performance of “I'll Walk Alone” by Dinah Shore is considered one of her finest works, showcasing her mastery over musical phrasing and interpreting emotions through music.

“I'm Making Believe” by Ella Fitzgerald & Ink Spots

Song Year: 1944

“I'm Making Believe” is a jazz and swing music classic composed by James V. Monaco with lyrics penned by Mack Gordon in 1944. This masterpiece was first recorded by the Ink Spots and the legendary Ella Fitzgerald as their guest vocalist for the song.

The collaboration between these musical luminaries produced amazing harmonies that left an indelible impression on listeners worldwide.

“Twilight Time” by Les Brown

Song Year: 1944

“Twilight Time” is a captivating and melodic tune that brings back memories of the Big Band era. This song was performed by Les Brown and featured in our list of Best Songs from 1944.

Les Brown's musical arrangements and sheer artistry on this number make it one of his most memorable recordings. The composition conveys a magical nostalgia, which resonates with listeners today.

“It's Love-Love-Love” by Guy Lombardo

Song Year: 1944

One of the most popular love songs from 1944 is “It's Love-Love-Love” by Guy Lombardo and his Royal Canadians. The song, written by Jule Styne and Sammy Cahn, quickly became a hit among audiences during the swing era.

In addition to its popularity in 1944, “It's Love-Love-Love” has continued to maintain a presence in pop culture. Guy Lombardo himself even appeared on Route 66, where he played himself and performed the song in an episode titled “But What Do..”

“My Heart Tells Me” by Glen Gray

Song Year: 1944

One of the most romantic ballads 1944, “My Heart Tells Me,” was recorded by Glen Gray with his Casa Loma Orchestra. Eugenie Baird did the vocals. It served as the theme song to the popular musical film Sweet Rosie O'Grady in 1943 and was later included on several compilation albums showcasing the best songs from that year.

With its beautiful melody and soul-stirring lyrics, “My Heart Tells Me” captured the hearts of listeners nationwide. The track became a standout hit during an era when jazz orchestras were dominating popular music charts.

“I Love You” by Bing Crosby

Song Year: 1944

“I Love You” is one of the greatest love songs of all time and a popular tune from the golden age of music. The song was written by Cole Porter in 1944 and featured on Bing Crosby's album of the best songs from that year.

The popularity of “I Love You” can be attributed to its strong, captivating lyrics and enticing melody. The romantic nature of the song makes it timeless, as it still resonates with audiences today.

It is worth noting that while “I Love You” made it onto Bing Crosby's album, some other number-one hits were omitted. Nonetheless, this does not detract from what has become one of his most famous recordings.

“Straighten Up And Fly Right” by The King Cole Trio

Song Year: 1944

Straighten Up and Fly Right is an iconic song from 1944 written by Irving Mills and Nat King Cole. It was among the first vocal hits from the King Cole Trio, featuring Cole's silky smooth voice on top of a jazzy melody.

The song became an instant hit, topping the black charts in 1944 and selling over half a million copies.

Nat King Cole wrote, sang, and played piano on the song, showcasing his skills as a five-tool jazz player. The lyrics are based on one of Cole's father's sermons, emphasizing the importance of taking responsibility for oneself and moving forward positively.

“Long Ago” by Dick Haymes And Helen Forrest

Song Year: 1944

“Long Ago (And Far Away)” is one of the best songs from 1944 and was a romantic ballad that captured the hearts of listeners across America.

This popular song was recorded in 1944 with Tutti Camarata's orchestra on the Decca label. It was also performed by other artists such as Bing Crosby and Jo Stafford with Paul Weston's Orchestra, Andy Russell, and Louis Jordan & his Tympany Five, to name but a few.

“I'll Be Seeing You” by Bing Crosby

Song Year: 1944

“I'll Be Seeing You” by Bing Crosby was one of the most popular songs from 1944. The song is a classic American romantic ballad covered by many artists over the years.

Sammy Fain and Irving Kahal originally wrote the song for a musical comedy in 1938. However, it only gained significant popularity after being featured in a wartime film called “I'll Be Seeing You,” starring Ginger Rogers and Joseph Cotten.

“Amor” by Andy Russell

Song Year: 1944

One of the standout songs from 1944 was “Amor” by Andy Russell, a singer with several chart-topping hits during that year. The romantic song became an instant classic and remains popular to this day.

Russell had four top-ten hits on the Billboard Hot 100 Chart in 1944 alone, including “Amor.” The Latin-inspired tune was a departure from the typical big band sound of the time and helped pave the way for Latin music's later popularity.

“Mairzy Doates” by Merry Macs

Song Year: 1944

The Merry Macs were a popular close-harmony pop group in the 1940s. In 1944, they released a surprise hit with their rendition of “Mairzy Doates,” a children's song that became infamous worldwide.

“Mairzy Doates” appeared on “America's Greatest Hits 1944 (4CD),” alongside other popular songs from that year. It is considered a number-one hit for 1944, along with “Shoo Shoo Baby” by The Andrews Sisters.

“Besame Mucho” by Jimmy Dorsey

Song Year: 1944

Jimmy Dorsey, a prominent bandleader and musician during the 1930s and 1940s, produced one of that era's most iconic love songs: “Besame Mucho.” This classic tune captures the hearts of many with its sentimental lyrics and smooth melodies.

Dorsey wasn't alone in making this song popular – he shared the spotlight with Bing Crosby. Their collaboration on “Besame Mucho” further solidified its status as a beloved romantic ballad.

Top Songs From 1944, Final Thoughts

In the golden era of music, 1944 was a year that produced many iconic and memorable songs. From swing to jazz to big band, this year's top hits were diverse and captured the hearts of audiences worldwide.

Bing Crosby, Judy Garland, Glen Gray, and Les Brown were legendary artists who made an impact with their music in 1944. With so much great music, it's no wonder that compiling a list of the best songs from 1944 was challenging and exciting.