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Who sang these songs from the 20s?

Question 1
Who sang the famous song "Lonesome Little Raindrop" in 1920?
Question 2
Who sang the famous song "Oh Judge (He Treats Me Mean)" in 1920?
Question 3
Who sang the famous song "Gypsy Blues" in 1921?
Question 4
Who sang the famous song "Twelve O'Clock at Night" in 1924?
Question 5
Who sang the famous song "Marguerite" in 1927?
Question 6
Who sang the famous song "Bobbed Haired Bobby" in 1924?
Question 7
Who sang the famous song "Broken Hearted Melody" in 1923?
Question 8
Who sang the famous song "Horsey Keep Your Tail Up" in 1923?
Question 9
Who sang the famous song "Three O'Clock in The Morning" in 1923?
Question 10
Who sang the famous song "Piccolo Pete" in 1929?
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