Timeless Love Songs of the 1920s

22nd January 1926: Female flappers kicking, dancing, and having fun while musicians perform during a Charleston dance contest at the Parody Club. Photo by Hulton Archive/Getty Images
22nd January 1926: Female flappers kicking, dancing, and having fun while musicians perform during a Charleston dance contest at the Parody Club. Photo by Hulton Archive/Getty Images

During the 1920s, also called "The Roaring 20s," jazz became very popular. Chicago became the jazz capital and vocalists like Billie Holiday soon grabbed the spotlight.

Songs from Broadway musicals were also gaining traction, especially songs by legendary composer Irving Berlin. If you listen closely to the love songs of this period, you'll notice that the lyrics are well-written and poem-like. One of the notable singers during this time was Ruth Etting, also known as "America's Sweetheart of Song."

"Ain't Misbehavin'" - Thomas "Fats" Waller

The song "Ain't Misbehavin'" was written in 1929 by Thomas "Fats" Waller, Harry Brooks and Andy Razaf.

It was first recorded by Fats Waller but recordings by other artists soon followed, including Louis Armstrong, Ray Charles, Ella Fitzgerald and Sarah Vaughan. The song was also included in the 1943 film Stormy Weather featuring a memorable performance on the piano by Fats Waller. The lyrics follow:

No one to talk with,
All by myself,
No one to walk with,
But I'm happy on the shelf
Ain't misbehavin',
I'm savin' my love for you

"All Alone" - Irving Berlin

Published in 1924, this song was written by Irving Berlin. The song was later recorded by several vocalists including Frank Sinatra and Doris Day. An excerpt of the lyrics follows:

All alone, I'm so all alone
There is no one else but you
All alone by the telephone
Waiting for a ring, a ting-a-ling

"Always" - Irving Berlin

Another Irving Berlin song written in 1925, this was sung by Bettye Avery in the 1942 film, Pride of the Yankees. "Always" was recorded by Patsy Cline, Billie Holiday and other notable performers. An excerpt of the lyrics is below:

I'll be loving you always
With a love that's true always.
When the things you've planned
Need a helping hand,
I will understand always.

Listen to Patsy Cline sing "Always" from the movie The Pride of the Yankees.

"April Showers" - B.G. DeSylva

Published in 1921, the lyrics of this song was written by B.G. DeSylva and the music was composed by Louis Silvers. It was sung by Al Jolson in the 1921 musical Bombo and later recorded by him in 1932. Read the lyrics:

Life is not a highway strewn with flowers,
Still, it holds a goodly share of bliss,
When the sun gives way to April showers,
Here is the point you should never miss.

"Blue Skies" - Irving Berlin

With music and lyrics written by Irving Berlin in 1926, this song was performed by Belle Baker in the musical Betsy. "Blue Skies" was recorded by several singers from diverse genres, including Benny Goodman and Willie Nelson.

The song was also featured in several films including The Jazz Singer. An excerpt of the lyrics follows:

Blue skies smilin' at me
Nothin' but blue skies do I see
Bluebirds singin' a song
Nothin' but bluebirds all day long

Listen to Ella Fitzgerald singing "Blue Skies" via YouTube.

"Everybody Loves My Baby" - Jack Palmer

Composed by Jack Palmer and Spencer Williams in 1924, the complete title of this song is "Everybody Loves My Baby (But My Baby Don't Love Nobody But Me)."

This song was recorded by Aileen Stanley in 1924 and the Boswell Sisters in 1932. Follow the lyrics below:

Everybody loves my baby,
But my baby don't love nobody but me.
Nobody but me.
Everybody wants my baby,
But my baby don't want nobody but me
That's plain to see.

Listen to the Boswell Sisters singing this song courtesy of YouTube.

"I Can't Believe That You're In Love With Me" - Jimmy McHugh

Written by Jimmy McHugh and Clarence Gaskill in 1926, this song was recorded by Billie Holiday in 1933 and later by Frank Sinatra in 1960.

See the romantic lyrics below, and then listen to Billie Holiday singing "I Can't Believe That You're In Love With Me" from YouTube.

Your eyes so blue
Your kisses too
I never knew what they could do
I can't believe you're in love with me

"I Wanna Be Loved By You" - Bert Kalmar

Written in 1928 by Bert Kalmar, Harry Ruby, and Herbert Stothart, this song was made for the musical titled Good Boy. This song was recorded by Helen Kane, for which the cartoon character Betty Boop was based.

It was also performed by Marilyn Monroe in the 1959 film Some Like It Hot. Listen to Marilyn Monroe's version of this song, courtesy of YouTube, and read an excerpt of the lyrics:

I wanna kissed by you, just you,
Nobody else but you,
I wanna be kissed by you, alone!

"Side By Side" - Harry Woods

The melody of this song was composed by Harry Woods and the lyrics were written by Gus Kahn in 1927. This song was recorded by Kay Starr in 1953 and several other performers also recorded this very familiar tune.

Discover the lyrics below and then listen to Kay Starr singing "Side By Side."

Oh, we ain't got a barrel of money,
Maybe we're ragged and funny;
But we'll travel along, singin' a song,
Side by side.

"Stardust" - Hoagy Carmichael

The melody of this song was written in 1927 by Hoagy Carmichael and the lyrics were added by Mitchell Parish two years later. It was first recorded in 1927 by Emil Seidel and became a hit in 1930 with Isham Jones' version.

This song became so popular that many prominent singers and bands recorded it, including Louis Armstrong, Bing Crosby, Benny Goodman, and Nat King Cole. An excerpt of the lyrics follows:

Sometimes I wonder why I spend
The lonely nights
Dreaming of a song.
The melody haunts my reverie
And I am once again with you.
When our love was new, and each kiss an inspiration.
But that was long ago, and now my consolation
Is in the stardust of a song.

Listen to Nat King Cole singing "Stardust."

"The Best Things In Life Are Free" - Lew Brown

This song was written by Lew Brown, B.G. DeSylva and Ray Henderson for the 1927 musical Good News.

In 1930, a film version of the musical was produced. In 1956, a movie musical based on the lives of the writers of this song was produced. Follow the lyrics:

The moon belongs to everyone
The best things in life are free,
The stars belong to everyone
They gleam there for you and me.

Listen to Jo Stafford sing this song on YouTube.

"The Song Is Ended" - Irving Berlin

"The Song Is Ended" is another unforgettable Irving Berlin composition written in 1927 with lyrics by Beda Loehner.

The complete title of this song is "The Song Is Ended (But The Melody Lingers On)." It was recorded in 1927 by Ruth Etting and the lyrics can be found below.

The song is ended
But the melody lingers on
You and the song are gone
But the melody lingers on

"What'll I Do" - Irving Berlin

This beautiful song was written by Irving Berlin in 1923 and was included in his Music Box Revue Of 1924.

The song has been performed and recorded by various artists. Among them are Grace Moore, Johnny Mathis, and Perry Como. The lyrics follow:

What'll I do
When you are far away
And I am blue
What'll I do

Watch Mitzi Gaynor's rendition of this classic song.

"When You're Smiling" - Mark Fisher

This 1928 song was composed by Mark Fisher, Joe Goodwin, and Larry Shay. It was first recorded by Louis Armstrong in 1929 but many other recordings soon followed, including the very popular rendition by Frank Sinatra.

The complete title of this song is "When You're Smiling (The Whole World Smiles With You)." Follow an excerpt of the lyrics:

When you're smiling
When you're smiling
The whole world smiles with you

"With A Song In My Heart" - Lorenz Hart

This song is by Lorenz Hart and Richard Rodgers from their 1929 musical Spring Is Here. Renditions by other performers were soon recorded and it was also included in several other musical productions. An excerpt of the lyrics follows:

With a song in my heart
I behold your adorable face.
Just a song at the start
but it soon is a hymn to your grace​

Listen to Doris Day singing "With A Song In My Heart" from YouTube.

"Without A Song" - William Rose

Published in 1929, the lyrics were written by William Rose and Edward Eliscu, and the melody composed by Vincent Youmans. This song was recorded by Perry Como, Frank Sinatra, and other famous performers. Read the lyrics:

Without a song, the day would never end
Without a song, the road would never have been
When things go wrong, a man ain't got a friend
Without a song

Listen to Kay Starr singing "Without A Song" as a courtesy from YouTube.

"Who's Sorry Now" - Bert Kalmer

In this song, the words are by Bert Kalmer and Harry Ruby, and the music is by Ted Snyder. This song was published in 1923 and was featured in the 1950 film Three Little Words.

The most famous recording of this song is by Connie Francis who made it a hit in 1958. The lyrics follow:

Who's sorry now, who's sorry now
Whose heart is achin' for breakin' each vow
Who's sad and blue, who's cryin' too
Just like I cried over you