| 1 | Have Yourself A Merry Little Christmas | 1944 |  |
| Judy Garland |
| 2 | Have Yourself A Merry Little Christmas | Dec 1957 | |
| Frank Sinatra |
| 3 | Have Yourself A Merry Little Christmas | Dec 1963 | |
| Johnny Mathis |
| 4 | Have Yourself A Merry Little Christmas | Dec 1967 | |
| Barbra Streisand |
| 5 | Have Yourself A Merry Little Christmas | Dec 1978 | |
| Carpenters |
| 6 | Have Yourself A Merry Little Christmas | Dec 1986 | |
| Crystal Gayle |
| 7 | Have Yourself A Merry Little Christmas | Dec 1987 | |
| The Pretenders |
| 8 | Have Yourself A Merry Little Christmas | Dec 1989 | |
| Lou Rawls |
| 9 | Have Yourself A Merry Little Christmas | Dec 1994 | |
| Kenny G |
| 10 | Have Yourself A Merry Little Christmas | Dec 2000 | |
| Christina Aguilera |
| 11 | Have Yourself A Merry Little Christmas | Dec 2001 | |
| James Taylor |
| 12 | Have Yourself A Merry Little Christmas | Dec 2006 | |
| Sarah McLachlan |
| 13 | Have Yourself A Merry Little Christmas | Dec 2007 | |
| Barry Manilow |
| 14 | Have Yourself A Merry Little Christmas | Dec 2007 | |
| Twisted Sister |
| 15 | Have Yourself A Merry Little Christmas | Dec 2007 | |
| Sister Hazel |
| 16 | Have Yourself A Merry Little Christmas | Dec 2007 | |
| Captain & Tennille |
| 17 | Have Yourself A Merry Little Christmas | Dec 2009 | |
| David Archuleta & Charice Pempengco |
| 18 | Have Yourself A Merry Little Christmas | Dec 2009 | |
| Michael Buble |
| 19 | Have Yourself A Merry Little Christmas | Dec 2009 | |
| Keyshia Cole |
| 20 | Have Yourself A Merry Little Christmas | Dec 2009 | |
| Francesca Battistelli |
| 21 | Have Yourself A Merry Little Christmas | Dec 2009 | |
| Ledisi |
| 22 | Have Yourself A Merry Little Christmas | Dec 2009 | |
| Colbie Caillat |
| 23 | Have Yourself A Merry Little Christmas | Dec 2009 | |
| Michael McDonald |
| 24 | Have Yourself A Merry Little Christmas | Dec 2010 | |
| Katharine McPhee |
| 25 | Have Yourself A Merry Little Christmas | Dec 2012 | |
| Ali & Theo |
| 26 | Have Yourself A Merry Little Christmas | Dec 2012 | |
| Rod Stewart |
| 27 | Have Yourself A Merry Little Christmas | Dec 2012 | |
| Victoria Duffield |
| 28 | Have Yourself A Merry Little Christmas | Dec 2013 | |
| Susan Boyle |
| 29 | Have Yourself A Merry Little Christmas | Dec 2013 | |
| Jewel |
| 30 | Have Yourself A Merry Little Christmas | Dec 2013 | |
| Mary J. Blige |
| 31 | Have Yourself A Merry Little Christmas | Dec 2013 | |
| Cat Power |
| 32 | Have Yourself A Merry Little Christmas | Dec 2014 | |
| Sam Smith |
| 33 | Have Yourself A Merry Little Christmas | Dec 2014 | |
| Dan + Shay |
| 34 | Have Yourself A Merry Little Christmas | Dec 2014 | |
| Melina Featuring Paul Brown |
| 35 | Have Yourself A Merry Little Christmas | Dec 2014 | |
| Blue Rodeo |