DESCRIPTION:
It took longer then I thought, but "Top 20 Greatest Songs 1920-1929" is here. Like the other two videos, I used the same source, and made a few very minor changes. Enjoy the video.

Song list:

20. Someone to Watch Over Me - Gertrude Lawrence (1927)
19. Some of These Days - Sophie Tucker with Ted Lewis (1927)
18. Three O'Clock in the MOrning - Paul Whiteman (1922)
17. Rhapsody in Blue - George Gershwin with Paul Whiteman and his Orchestra (1924)
16. The Man I Love - Marion Harris (1928)
15. My Melancholy Baby - Gene Austin (1927)
14. Blue Yodel #1 (T for Texas) - Jimmy Rodgers (1928)
13. Sonny Boy - Al Jolson (1928)
12. Always - Vincent Lopez (1926)
11. Ol' Man River - Paul Whiteman and his Orchestra with Bing Crosby (1928)
10. It Had to be You - Isham Jones (1924)
9. I Can't Give You Anything but Love - Cliff Edwards (1928)
8. St. Louis Blues - W.C. Handy (1923)
7. Whispering - Paul Whiteman (1920)
6. April Showers - Al Jolson (1922)
5. Dardanella - Ben Selvin (1920)
4. Ain't Misbehavin' - Fats Waller (1929)
3. Swanee - Al Jolson (1920)
2. The Prisoner's Song - Vernon Dalhart (1925)
1. My Blue Heaven - Gene Austin (1927)

Source:
http://davesmusicdatabase.blogspot.com/2012/04/top-songs-by-decade-1900-present.html