Music Lists Are Us: Favorite 1920s Songs by Year, with brief comments

1920

St. Louis Blues by Marion Harris

1921

Ain't We Got Fun by Van and Schenk

1922

Sheik of Araby by Ray Miller

Downhearted Blues by Bessie Smith

I'm Just Wild About Harry by Marion Harris

I Wish I Could Shimmy Like My Sister Kate by The Georgians or Eva Taylor

Rhapsody in Blue by George Gershwin and The Paul Whiteman Orchestra

Fascinating Rhythm by George and Ira Gershwin, sung by Cliff (Ukulele Ike) Edwards

1925

Sweet Georgia Brown by Ben Bernie or Ethel Waters

Yes Sir, That's My Baby by Gene Austin

Tea for Two by Marion Davis

1926

Heebie Jeebies by Louis Armstrong & His Hot Five

Bye Bye Blackbird by Gene Austin

Black Bottom Stomp by Jelly Roll Morton

St. James Infirmary by Louis Armstrong & His Hot Five

Gimme a Little Kiss, Will Ya Huh? by Jack Smith

Big Butter and Egg Man by Louis Armstrong

Dinah by Ethel Waters

1927

Me and My Shadow by Jack Smith

Stardust by Hoagy Carmichael

My Blue Heaven by Gene Austin (the 2nd biggest selling non-holiday record of the pre-rock era)

East St. Louis Toodle-oo by Duke Ellington (covered by Steely Dan on their 1974 album Pretzel Logic)

Ain't She Sweet by Ben Bernie

'Deed I Do by Ruth Etting

Blue Skies by Irving Berlin, performed by Ben Selvin & his Orchestra

I Can't Give You Anything But Love, Baby by Cliff (Ukulele Ike) Edwards

Statesboro Blues by Blind Willie McTell

When You're Smiling by Louis Armstrong

If I Had You by Rudy Vallee

Makin' Whoopee by Eddie Cantor

Am I Blue? by Ethel Waters

An American in Paris by George Gershwin

Ain't Misbehavin' by Fats Waller

Nobody Knows You When You're Down and Out by Bessie Smith