Harry Macdonough — “When You Were Sweet Sixteen” — YouTube

(George J. Gaskin’s recording of this song) was the most popular recording in 1900, but I couldn’t find a recording; Macdonough’s recording is from 1901.

Arthur Collins — “Ma Tiger Lily” (#2) — Archive.org

Steve Porter — “A Bird in a Gilded Cage” (#3) — YouTube

Arthur Collins — “Mandy Lee” (#4) — Archive.org

Vess Ossman — “A Coon Band Contest” (#17) — Archive.org

Harry Macdonough — “The Holy City” (#19) — Archive.org

J.W. Myers — “Good-Bye, Dolly Gray” (#21) — Archive.org