[0:00] ? Let It Snow (instrumental)
[1:16] ? Deck The Halls (choir)
[2:41] ?
[4:19] ? White Christmas (male vocal with group?)
[7:20] ? The First Noel (choir)
[10:21] I'm Sending A Letter To Santa Claus - Vera Lynn (1939)
[12:08] ? O Come All Ye Faithful (choir)
[20:25] Bow Wow Wants a Boy for Christmas - Red Buttons (1954)
[23:53] ? Silent Night (choir)
[27:07] Christmas Island - Jack McLean and His Orchestra with Wayne Gregg (1947)
[30:20] I'd Like a Boyfriend for Christmas - Janet Lane and Rhythm Westerners (1951)
[33:12] ? Joy To The World
[37:12] ? Medley (The First Noel/God Rest Ye Merry Gentlemen/?)
[40:26] ? cut off White Christmas
[43:57] Christmas Story - Phil Regan with Leo Arnaud and His Orchestra and The Jud Conlon Choir (1950)
[47:04] When It's Christmas on the Range - Eddy Howard with Orchestra (1940)
[50:03] I'm Tired of Playing Santa Claus to You - Cowboy Copas with String Band (1947)
[53:10] ? Medley - (?/?/Jingle Bells/sing a song of the holly?/O Christmas Tree/?/God Rest Ye Merry Gentleman/?/Over The River & Through The Woods/etc)
[1:02:15] Let's Dance Theme - Benny Goodman And His Orchestra (Chicago Congress Hotel 1935)
[1:03:22] Jingle Bells - Benny Goodman And His Orchestra (Chicago Congress Hotel 1935)
[1:06:19] Where Am I - Benny Goodman And His Orchestra with Helen Ward (Chicago Congress Hotel 1935)
[1:09:41] You Forgot To Remember - Benny Goodman And His Orchestra (Chicago Congress Hotel 1935)
[1:15:37] Get Happy - Benny Goodman And His Orchestra (Chicago Congress Hotel 1935)
[1:18:52] (cut-off) Basin Street Blues Benny Goodman And His Orchestra with Joe Harris (Chicago Congress Hotel 1935)
[1:24:54] Limehouse Blues - Benny Goodman And His Orchestra (Chicago Congress Hotel 1935)
[1:27:11] Some Day Sweetheart - Benny Goodman And His Orchestra (Chicago Congress Hotel 1935)
[1:30:11] I Told Santa Claus To Bring Me You - Bernie Cummins and His Orchestra (1930)
[1:35:48] My Christmas Song For You - Hoagy Carmichael and Orchestra with Martha Mears (1945)
[1:39:04] Let's Light the Christmas Tree - Jack Brown and The Three Jills (1948)
[1:43:35] Santa Claus is Comin' to Town - American Novelty Orchestra (1935)
[1:50:04] ? Hark The Herald Angels Sing
[1:52:52] ? Jingle Bells
[1:55:14] Silent Night - Kate Smith (1940)
[2:02:21] Reindeer Rock - Jimmy Boyd (1955)
Loops in different orders after this point
Note: [1:02:15 - 1:27:11] Are all from an NBC Broadcast from Chicago's Congress Hotel- Benny Goodman And His Orchestra (1935) - (Let's Dance-Theme/Jingle Bells/Where Am I (with Helen Ward)/You Forgot To Remember/The Music Goes 'Round And 'Round (with Joe Harris)/Get Happy/Basin Street Blues (cut-off)/I've Got A Feeling You're Fooling (with Helen Ward)/That's You, Sweetheart (with Helen Ward)/Limehouse Blues/Some Day Sweetheart).
Special thanks to J for this list!
Underlined songs are linked to either a YouTube video of the song or to a recording of the song from the Internet Archive. Question marks mean the song is unknown.
Same/very similar song order in other streams: