Bing Crosby Popular Song Rankings [2026]

Winter WonderlandBing Crosby8rank/position

Winter Wonderland (Remastered 2006)

The classic Christmas jazz number “Winter Wonderland.” This song has a very long history; it was composed in 1934 by composer Felix Bernard and lyricist Richard Bernhard Smith.

It has been covered by a variety of jazz vocalists such as Tony Bennett and Darlene Love, and versions with arrangements from other genres are still being released today.

This time, I’ve chosen the version by the world-renowned jazz vocalist Bing Crosby.

expand_lessRaise the rankingexpand_morelower

Ryo

Report a problem

Irish lullabyBing Crosby9rank/position

Bing Crosby: Too-Ra-Loo-Ra-Loo-Ral (Thats An Irish Lullaby)

A song by Bing Crosby, one of America’s first multi-entertainers.

Since 1940, he achieved great success as a singer.

He mainly sang Christmas songs and was even called the “King of Christmas.” His lifetime record sales total 400 million.

Little Jack Frost, Get LostBing Crosby & Peggy Lee10rank/position

Bing Crosby & Peggy Lee – Little Jack Frost Get Lost (Decca Records 1952)

A cheerful duet by Bing Crosby and Peggy Lee that chases away winter’s chill with a sprightly rhythm.

Released as a single by Decca Records in 1952, the song humorously portrays people asking the personified cold, “Jack Frost,” to leave.

Crosby’s rich baritone and Lee’s gentle vocals blend in exquisite harmony, vividly depicting winter scenes—grumbling sweethearts, a rose frozen stiff, and more.

Infused with swing and jazz elements, it’s perfect for those seeking a warm atmosphere during the Christmas season, and it remains a perennial favorite frequently included on holiday albums.

Peace On Earth / Little Drummer BoyBing Crosby, David Bowie11rank/position

Bing Crosby, David Bowie – Peace On Earth / Little Drummer Boy

This song is known as a masterpiece born from an unlikely pairing.

Bing Crosby’s rich, resonant voice and David Bowie’s clear vocals create a wonderfully balanced harmony.

The structure, which blends a traditional carol with a new composition, beautifully expresses the warmth of Christmas and a wish for peace.

Recorded in September 1977 and released as a single in 1982 after Crosby’s sudden passing, it became a major hit, reaching No.

3 in the UK, and has continued to be cherished in North America as a Christmas staple.

Enjoyable across generations, this piece is perfect for the holiday season—an ideal soundtrack for warm moments with family and friends.