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Who sang these songs from the 20s?

Question 1
Who sang the famous song "Learn to Smile" in 1921?
Question 2
Who sang the famous song "Copenhagen" in 1925?
Question 3
Who sang the famous song "Love Sends a Little Gift of Roses" in 1923?
Question 4
Who sang the famous song "Chicago (That Toddlin' Town)" in 1922?
Question 5
Who sang the famous song "Irene" in 1920?
Question 6
Who sang the famous song "Girlfriend" in 1926?
Question 7
Who sang the famous song "My Angel (Angela Mia)" in 1928?
Question 8
Who sang the famous song "Covered Wagon Days" in 1924?
Question 9
Who sang the famous song "Ol' Man River" in 1928?
Question 10
Who sang the famous song "Laugh, Clown, Laugh!" in 1928?
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