| 1 | ![Overture by Gypsy 2008 Broadway Cast]() | Overture | Gypsy 2008 Broadway Cast | B♭ Major | 6B | 144 |
| 2 | ![May We Entertain You by Sami Gayle, Emma Rowley, Patti LuPone]() | May We Entertain You | Sami Gayle, Emma Rowley, Patti LuPone | D♭ Major | 3B | 50 |
| 3 | ![Some People by Patti LuPone]() | Some People | Patti LuPone | C Major | 8B | 132 |
| 4 | ![Seattle to Los Angeles by Patti LuPone]() | Seattle to Los Angeles | Patti LuPone | C Major | 8B | 130 |
| 5 | ![Small World by Patti LuPone, Boyd Gaines]() | Small World | Patti LuPone, Boyd Gaines | B Major | 1B | 85 |
| 6 | ![Baby June and her Newsboys / Let Me Entertain You by Sami Gayle, Emma Rowley, Gypsy 2008 Broadway Cast]() | Baby June and her Newsboys / Let Me Entertain You | Sami Gayle, Emma Rowley, Gypsy 2008 Broadway Cast | G Major | 9B | 69 |
| 7 | ![Have an Eggroll, Mr Goldstone by Patti LuPone, Boyd Gaines, Leighann Larkin, Bill Bateman & Ensemble]() | Have an Eggroll, Mr Goldstone | Patti LuPone, Boyd Gaines, Leighann Larkin, Bill Bateman & Ensemble | B Major | 1B | 99 |
| 8 | ![Little Lamb by Laura Benanti]() | Little Lamb | Laura Benanti | F♯ Major | 2B | 77 |
| 9 | ![You'll Never Get Away from Me by Patti LuPone, Boyd Gaines]() | You'll Never Get Away from Me | Patti LuPone, Boyd Gaines | A♭ Major | 4B | 175 |
| 10 | ![Dainty June and her Farmboys by Leighann Larkin, Gypsy 2008 Broadway Cast]() | Dainty June and her Farmboys | Leighann Larkin, Gypsy 2008 Broadway Cast | C Major | 8B | 122 |
| 11 | ![Broadway by Leighann Larkin, Gypsy 2008 Broadway Cast]() | Broadway | Leighann Larkin, Gypsy 2008 Broadway Cast | C Major | 8B | 117 |
| 12 | ![If Momma Was Married by Leighann Larkin, Laura Benanti]() | If Momma Was Married | Leighann Larkin, Laura Benanti | A♭ Major | 4B | 97 |
| 13 | ![All I Need Is the Girl by Tony Yazbeck, Laura Benanti]() | All I Need Is the Girl | Tony Yazbeck, Laura Benanti | C Major | 8B | 113 |
| 14 | ![Everything's Coming Up Roses by Patti LuPone]() | Everything's Coming Up Roses | Patti LuPone | B♭ Major | 6B | 93 |
| 15 | ![Madam Rose's Toreadorables by Patti LuPone, Laura Benanti, Gypsy 2008 Broadway Cast]() | Madam Rose's Toreadorables | Patti LuPone, Laura Benanti, Gypsy 2008 Broadway Cast | E♭ Major | 5B | 161 |
| 16 | ![Together Wherever We Go by Patti LuPone, Boyd Gaines, Laura Benanti]() | Together Wherever We Go | Patti LuPone, Boyd Gaines, Laura Benanti | A Minor | 8A | 108 |
| 17 | ![You Gotta Get a Gimmick by Alison Fraser, Marilyn Caskey, Lenora Nemetz]() | You Gotta Get a Gimmick | Alison Fraser, Marilyn Caskey, Lenora Nemetz | C Major | 8B | 113 |
| 18 | ![The Strip by Jim Bracchitta, Alison Fraser, Laura Benanti, Patti LuPone, Gypsy 2008 Broadway Cast]() | The Strip | Jim Bracchitta, Alison Fraser, Laura Benanti, Patti LuPone, Gypsy 2008 Broadway Cast | B♭ Minor | 3A | 92 |
| 19 | ![Rose's Turn by Patti LuPone]() | Rose's Turn | Patti LuPone | F Minor | 4A | 122 |
| 20 | ![Tomorrow's Mother's Day - Bonus Track by Sami Gayle, Emma Rowley]() | Tomorrow's Mother's Day - Bonus Track | Sami Gayle, Emma Rowley | G Major | 9B | 140 |
| 21 | ![Mother's Day - Alternate Version, Bonus Track by Sami Gayle]() | Mother's Day - Alternate Version, Bonus Track | Sami Gayle | A♭ Major | 4B | 165 |
| 22 | ![Small World / Momma's Talkin' Soft - Bonus Track by Patti LuPone, Sami Gayle, Emma Rowley, Boyd Gaines]() | Small World / Momma's Talkin' Soft - Bonus Track | Patti LuPone, Sami Gayle, Emma Rowley, Boyd Gaines | B Major | 1B | 94 |
| 23 | ![Nice She Ain't - Bonus Track by Boyd Gaines]() | Nice She Ain't - Bonus Track | Boyd Gaines | E Major | 12B | 131 |
| 24 | ![Smile, Girls - Bonus Track by Patti LuPone]() | Smile, Girls - Bonus Track | Patti LuPone | F Major | 7B | 70 |
| 25 | ![Who Needs Him? - Bonus Track by Patti LuPone]() | Who Needs Him? - Bonus Track | Patti LuPone | G Major | 9B | 63 |
| 26 | ![Three Wishes for Christmas - Bonus Track by Tony Yazbeck, Gypsy 2008 Broadway Cast]() | Three Wishes for Christmas - Bonus Track | Tony Yazbeck, Gypsy 2008 Broadway Cast | E♭ Major | 5B | 140 |