These are the top 100 songs from the first decade (1900-1909) of the 20th century according to Dave’s Music Database.
- You’re a Grand Old Flag (aka “The Grand Old Rag”)…Billy Murray (1906)
- Sweet Adeline (You’re the Flower of My Heart)…Haydn Quartet (1904)
- Take Me Out to the Ball Game…Haydn Quartet (1908)
- I Wonder Who’s Kissing Her Now…Henry Burr (1909)
- School Days (When We Were a Couple of Kids)…Byron Harlan (1907)
- My Gal Sal…Byron Harlan (1907)
- Give My Regards to Broadway…Billy Murray (1905)
- The Glow-Worm…Victor Orchestra (1908)
- Shine on, Harvest Moon…Harry MacDonough with Miss Walton (1909)
- In the Good Old Summer Time…J.W. Myers (1902)
- Meet Me in St. Louis, Louis…Billy Murray (1904)
- In My Merry Oldsmobile…Billy Murray (1905)
- Yankee Doodle Boy…Billy Murray (1905)
- Wait Till the Sun Shines, Nellie…Byron Harlan (1906)
- Put on Your Old Grey Bonnet…Haydn Quartet (1909)
- Bill Bailey, Won’t You Please Come Home…Arthur Collins (1902)
- In the Shade of the Old Apple Tree…Henry Burr (1905)
- The Preacher and the Bear…Arthur Collins (1905)
- A Bird in a Gilded Cage…Steve Porter (1900)
- Bedelia…Haydn Quartet (1904)
- The Stars and Stripes Forever…John Philip Sousa’s Band (1901)
- Tell Me, Pretty Maiden…Harry MacDonough with Grace Spencer (1901)
- On a Sunday Afternoon…J.W. Myers (1902)
- Nobody…Bert Williams (1906)
- Pagliacci, Act I: Vesti La Giubba (On with the Play) (LEONCAVALLO)…Enrico Caruso (1907)
- Hiawatha (His Song to Minnehaha)…Harry MacDonough (1903)
- Harrigan…Billy Murray (1907)
- Under the Bamboo Tree…Arthur Collins (1902)
- Hello Central, Give Me Heaven…Byron Harlan (1901)
- Mighty Like a Rose (aka “Mighty Lak a Rose”)…George Alexander (1903)
- Arkansaw Traveler…Len Spencer (1902)
- When You Were Sweet Sixteen…George J. Gaskin (1900)
- Maple Leaf Rag…U.S. Marine Band (1907)
- Toyland…Haydn Quartet with Corrine Morgan (1904)
- Down Where the Wurzburger Flows…Arthur Collins & Byron Harlan (1903)
- Goodbye, Dolly Gray…Big Four Quartet (1901)
- The Yama Yama Man…Ada Jones with the Victor Light Orchestra Co. (1909)
- Under the Anhauser Bush…Arthur Collins & Byron Harlan (1904)
- Silver Threads Among the Gold…Richard Jose (1904)
- Navajo…Billy Murray (1904)
- Love Me and the World Is Mine…Henry Burr (1906)
- Everybody Works But Father…Billy Murray (1905)
- I’ve Got Rings on My Fingers…Blanche Ring (1909)
- Goodbye, My Lady Love…Henry Burr (1904)
- The Mansion of Aching Hearts…Harry MacDonough (1902)
- Cuddle Up a Little Closer, Lovey Mine…Billy Murray & Ada Jones (1908)
- Ma Blushin’ Rosie…Albert Campbell (1900)
- Swing Low, Sweet Chariot…Fisk Jubilee Singers (1909)
- Waltz Me Around Again Willie (‘Round, ‘Round, ‘Round)…Billy Murray with the Haydn Quartet (1906)
- Waiting at the Church (My Wife Won’t Let Me)…Ada Jones (1906)
- Sunbonnet Sue…Haydn Quartet (1908)
- Forty-Five Minutes from Broadway…Billy Murray (1906)
- Will You Love Me in December As You Do in May?...Haydn Quartet (1906)
- Come Down, Ma Evening Star…Mina Hickman (1903)
- Blue Bell…Byron Harlan with Frank Stanley (1904)
- Absence Makes the Heart Grow Fonder…Harry MacDonough (1901)
- Any Rags?...Arthur Collins (1903)
- Come Take a Trip in My Air-Ship…Billy Murray (1905)
- I Love a Lassie (My Scotch Bluebell)…Harry Lauder (1907)
- The Caissons Go Rolling Along (1906)
- I Can’t Tell You Why I Love You But I Do…Harry MacDonough (1900)
- In the Sweet Bye and Bye…Harry MacDonough with John Bieling (1903)
- Honey Boy…Columbia Male Quartet (1907)
- Alexander (Don’t You Love Your Baby No More?)…Billy Murray (1904)
- Teasing (I Was Only Teasing You)…Billy Murray (1904)
- Dear Old Girl…J.W. Myers (1903)
- A Coon Band Contest…Vess Ossman (1900)
- Red Wing (An Indian Fable)…Frank Stanley with Henry Burr (1907)
- The Bird on Nellie’s Hat…Helen Trix (1907)
- He’s a Cousin of Mine…Bert Williams (1907)
- How’d You Like to Spoon with Me?...Corrine Morgan with the Haydn Quartet (1906)
- Down in Jungle Town…Arthur Collins & Byron Harlan (1908)
- Ma Tiger Lily…Arthur Collins (1900)
- When It’s All Goin’ Out and Nothin’ Comin’ In…Bert Williams (1902)
- So Long, Mary…Corrine Morgan (1906)
- Daddy’s Little Girl…Byron Harlan (1906)
- Are You Sincere?...Elise Stevenson (1908)
- What You Goin’ to Do When the Rent Comes ‘Round? (Rufus Rastas Johnson Brown)…Arthur Collins (1905)
- Good Morning, Carrie…Bert Williams with George Walker (1902)
- Coax Me…Arthur Collins & Byron Harlan (1905)
- My Pony Boy…Ada Jones (1909)
- As Long As the World Rolls On…Alan Turner (1908)
- Down Under the Sugar Cane…Arthur Collins & Byron Harlan (1909)
- The Entertainer…Scott Joplin (1902)
- Would You Care?...Byron Harlan (1905)
- I Love, I Love, I Love My Wife, But Oh You Kid!...Arthur Collins (1909)
- Lift Every Voice and Sing…Johnson & Johnson (1900)
- Any Old Place I Hang My Hat Is “Home Sweet Home”…Will Denny (1901)
- Hurrah for Baffin’s Bay…Arthur Collins & Byron Harlan (1903)
- Way Down in Old Indiana…J.W. Myers (1902)
- Where the Morning Glories Twine Around the Door…Byron Harlan (1905)
- When Chloe Sings a Song…George J. Gaskin (1900)
- I Love you So (Merry Widow Waltz)…Victor Orchestra (1907)
- Goodbye, Eliza Jane…Arthur Collins (1903)
- The Tale of the Bumblebee…Harry MacDonough (1901)
- The Good Old U.S.A….Byron Harlan (1906)
- Good Evening, Caroline…Frank Stanley with Elise Stevens (1909)
- Dearie…Corrine Morgan with the Haydn Quartet (1905)
- When We Are M-A-R-R-I-E-D…Billy Murray & Ada Jones (1908)
- The Blue and the Gray (The Mother’s Gift to Her Country)…Byron Harlan (1900)