Bing Crosby Popular Song Rankings [2026]

Swinging on a starBing Crosby6rank/position

Bing Crosby – Swinging on a star

The song was composed by Jimmy Van Heusen, with lyrics written by Johnny Burke for the 1944 film “Going My Way.” Singing it with Bing Crosby are the Williams Brothers, including Andy Williams.

Frank Sinatra covered the song on his 1964 album.

White ChristmasBing Crosby7rank/position

White Christmas【Christmas Song】/ Bing Crosby -Piano Cover-

Composed by Irving Berlin, this piece has long been cherished as a symbol of Christmas.

It beautifully depicts Christmas scenes such as quiet landscapes blanketed with snow and children enjoying sledding.

Recorded by Bing Crosby in just 18 minutes on May 29, 1942, the song deeply resonated with people during World War II and offered precious comfort, especially to soldiers far from home.

When played on the piano, it brings out a different kind of poignancy and beauty from the original.

It’s a recommended song for anyone who wants to savor the Christmas atmosphere or reflect on memories with loved ones.

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.

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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.