Chart updated this week on: 2026-08-25
1.
Winter Wonderland
Kenny G
November 1, 1994
2.
(It Must've Been Ol') Santa Claus
Harry Connick, Jr.
October 26, 1993
3.
Greensleeves (What Child Is This?)
Kenny G
November 1, 1994
4.
I'm Gonna Be the First One (PCM Stereo Version)
Harry Connick, Jr.
October 28, 2003
5.
Christmas In Herald Square
Tony Bennett
September 29, 1998
6.
Christmas Time Again
Roy Edwin Williams & Francie
September 1, 2025
7.
It's Beginning to Look a Lot Like Christmas
April Varner
November 21, 2025
8.
Mary Did You Know (feat. Pam English)
Demetrius Nabors
November 23, 2024
9.
Winter Wonderland (feat. Kendrick Jackson)
Demetrius Nabors
November 23, 2024
10.
Silver Bells
Kenny G
November 1, 1994
11.
When My Heart Finds Christmas
Harry Connick, Jr.
January 1, 1993
12.
Medley: Deck the Halls / The Twelve Days of Christmas
Kenny G
January 1, 2002
13.
Santa Claus Is Coming To Town
Kenny G
February 20, 1999
14.
Nature Boy
Harry Connick, Jr.
October 28, 2003
15.
Have Yourself a Merry Little Christmas
Kenny G
November 1, 1994
16.
My Favorite Things
Yo-Yo Ma, Chris Botti, Romero Lubambo, Billy Kilson, Billy Childs & Robert Hurst
October 14, 2008
17.
It's Beginning to Look a Lot Like Christmas
Harry Connick, Jr.
August 19, 2010
18.
The First Noel (Live)
Tony Bennett, Plácido Domingo, Steven Mercurio, Vienna Symphony & Gumpoldskirchner Spatzen
October 15, 2001
19.
Joy to the World
Kenny G
January 1, 2002
20.
Sleigh Ride
Kenny G
February 20, 1999
21.
Here Comes Santa Claus
Doris Day & John Rarig
January 1, 1949
22.
Medley: Hark! The Herald Angels Sing/O Come All Ye Faithful
Kenny G
January 1, 2002
23.
Sleigh Ride
Harry Connick, Jr.
January 1, 1993
24.
Winter Weather (Mono Recording)
Peggy Lee & Benny Goodman
December 1, 1941
25.
Greensleeves (What Child Is This)
Peter White
August 11, 1997
26.
Let It Snow, Let It Snow, Let It Snow
Harry Connick, Jr.
January 1, 1993
27.
It's the Most Wonderful Time of the Year
Harry Connick, Jr.
September 22, 2008
28.
Silent Night
Kenny G
November 1, 1994
29.
Rudolph the Red-Nosed Reindeer
Harry Connick, Jr.
October 26, 1993
30.
Frosty The Snowman
Harry Connick, Jr.
October 28, 2003
31.
What Are You Doing New Year's Eve?
Harry Connick, Jr.
January 1, 1993
32.
Winter Wonderland
Chris Botti
October 22, 2002
33.
Winter Wonderland
Harry Connick, Jr.
September 22, 2008
34.
Little Drummer Boy
Kenny G
November 1, 1994
35.
White Christmas
Kenny G
November 1, 1994
36.
Jingle Bells
Harry Connick, Jr.
September 22, 2008
37.
The Christmas Waltz
Harry Connick, Jr.
October 28, 2003
38.
I'll Be Home For Christmas
Kenny G
February 20, 1999
39.
Hallelujah
Chris Botti
October 22, 2002
40.
I Pray On Christmas
Harry Connick, Jr.
January 1, 1993