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| Title | Genre | Singers | Scene | Description | Notes | |
| ACT 1 | ||||||
| 1 | Sing With Us (1:27) | Jazz in four part harmony | Company | 1 | A new Christmas carol is performed by tired carolers. | |
| 2 | Happy Crappy Christmas (2:25) | Jazz, Comedy | Pianist, Patrons | 1 | The patrons write a Christmas carol about drinking. | Slightly offensive content. Have Yourself a Merry Little Christmas by Hugh Martin and Ralph Blane, 1944. |
| 3 | My Christmas Guest List (4:21) | Ballad | Mary and Company | 3 | Mary sings to the homeless folk a song about why her atttude toward Christmas changed. | |
| 4 | Trim My Tree (4:00) | Jazz, Comedy | Beau | 4 | Beau serenades Holly to win a bet. | Mild sexual innuendo. This song includes a dance break. |
| 5 | The Path (4:44) | Gospel | Mary, Guitarist and Company | 5 | Carol and a street guitarist challenge Chase's motives. | |
| 6 | Couldn't I? (2:55) | Ballad, duet sung as a round | Olive, Holly, Harold and Gary | 6 | Olive serenades Harold while Holly pines for Beau. | |
| 7 | One Small Sign (2:45) | Ballad, Spiritual | Harold | 6 | Harold asks God for answers. | |
| 8 | Jesus's Birthday (2:21) | Jazz, Spiritual | Baa | 6 | Baa sings her own version of Happy Crappy Christmas. | |
| 9 | I'm Sincere (2:29) | Country-Western, Comedy | Don | 7 | Don smugly revels in his deception skills. | |
| 10 | Mad Mall Melee (3:26) | Jazz medley, Classical, Comedy | Company | 8 | A bell ringer solicits donations from exhausted shoppers while the mall Santa and vendors mock the shoppers. | Ode to Joy by Ludwig von Beethoven, 1824; Joy to the World melody by Lowell Mason, 1836; Christmas in the Valley by Dennis Whitty, 1986. |
| 11 | The Lost Sparrow (2:38) | Ballad | Mary and the Infirmed Children | 9 | Mary sings to the infirmed children. | This song includes a 45 second introduction while the scene changes. |
| 12 | I Wanted a Goat (7:39) | Jazz medley | Harold, Mary, Baa and the Infirmed Children | 9 | Harold, Mary and Baa explain heaven for pets to the infirmed children. | Good King Wenceslas by John Mason Neale and Thomas Helmore, 1853. This song contains instrumental arrangements of Couldn't I, One Small Sign and Jesus's Birthday. Parts of this song play in the background during dialogue. This song includes a dance break. |
| ACT 2 | ||||||
| 13 | That Star (3:25) | Waltz sung in four parts, Comedy | Company | 1 | The pilgrims create a new Christmas carol which is immediately mocked by the punks. | Slightly offensive lyrics. This song is performed in two parts separated by dialogue. |
| 14 | Western Kings (3:17) | Country-Western, Comedy | Mayor, Governor and President | 2 | The politicians decide to become the modern three kings. | We Three Kings by John Henry Hopkins Jr., 1857. |
| 15 | Open Me (4:03) | Jazz, Comedy | Holly and the Bartender | 3 | Holly serenades Beau. | Mild sexual innuendo. |
| 16 | Regrets (4:18) | Ballad | Harold, Don, Beau and Olive | 4 | Harold, Don, Beau and Olive reflect on their situations. | |
| 17 | I Believe in Santa Claus (3:11) | Jazz | The Punks | 5 | Don subdues the punks by forcing them to sing a children's song. | Jingle Bells by James Pierpont, 1857; Santa Claus is Coming to Town by Frederick Coots and Haven Gillespie, 1934. |
| 18 | Jesus's Birthday (R) (1:54) | Jazz, Spiritual | The Infirmed Children | 6 | Harold teaches the infirmed children Baa's song. | This song includes a dance break. |
| 19 | Open Me (R) (0:42) | Jazz, Comedy | Beau | 7 | Beau serenades his girlfriend overseas. | Mild sexual innuendo. |
| 20 | Couldn't I? (R) (1:07) | Ballad | Harold and Olive | 8 | Harold apologizes to Olive. | |
| 21 | Blessed Child (2:10) | Spiritual sung in four parts | Company | 9 | The pilgrims sing a Christmas carol to the coming child. | |
| 22 | Western Kings (R) (0:31) | Traditional | Mayor, Governor and President | 9 | The politicians present their gifts to the coming child. | We Three Kings by John Henry Hopkins Jr., 1857. |
| 23 | God Shouts (5:43) | Jazz, Spiritual | Harold and Company | 9 | Harold faces the pilgrims. | Parts of this song play in the background during dialogue. |
| 24 | Plow the Soil/They'll Say (3:50) | Jazz | Ray and Company | 9 | Finale. | Christmas in the Valley by Dennis Whitty, 1986. This song incorporates Sing With Us. Parts of this song play in the background during dialogue. |