Singer: Bing Crosby

Suave. Cool. And it wouldn't be Christmas without him. Uploaded by redteatral.net

How popular was Bing Crosby? Well, he sold more than a half billion records. In addition, he was a megastar in movies and on radio and TV. His “cool” style set the pace for everyone from Frank Sinatra to Michael Buble.

And when it comes to the holidays, Bing Crosby gave us the music of Christmas.

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Bing was the first person to be given a Lifetime Achievement Award by the Grammys. He was nominated for three Academy Awards, and won for Going My Way. As for ticket sales, it’s estimated that 1.07 billion tickets were bought for Bing’s movies, making him the third-most-popular movie star of all time, behind Clark Gable and John Wayne.

The very peak of Bing’s career may have been 1948, when he was voted the most admired man alive – even ahead of the Pope. And that year Music Digest estimated that Crosby recordings filled more than half of the 80,000 weekly hours allocated to recorded radio music. That’s hard to grasp.

But now it’s Christmas, the time most associated with Bing Crosby music today. His “White Christmas” is the best-selling single of all time, and his “Merry Christmas” is the all-time number one Christmas album. We love us some Bing Crosby at Christmas.

Song: “What a Wonderful World”

Do you consider this a Christmas song? Me neither, but it's played then. Go figure. Uploaded by fs2you.org.cn.

This Louis Armstrong song, which has become iconic in its usage in movies and TV shows, sold fewer than 1,000 copies in the U.S. when it was released in 1968. The good people of the U.K. heard it differently, however, and took the song to number one across the pond.

Uploaded by jazzrecordcenter.com.

“What a Wonderful World” finally made the charts stateside in 1971, when it was released in memoriam following the death of Louis Armstrong. It took an ironic use of the song during depressing scenes in the movie Good Morning, Vietnam (which has been done to death now, producers, so stop already) to take it to the top of the American charts.

Written by Bob Thiele and George David Weiss, the optimistic song is only two minutes, seventeen seconds long. For reasons beyond my simple understanding, it’s now being played as a Christmas song. Could it be the first line: “I see trees of green…”? Or is it its general feeling of goodwill toward men (“I see friends shaking hands, say how do you do/They’re really saying ‘I love you.'”)?

Some of the artists who’ve covered the song include: Eddy Arnold, Diana Ross, Israel Kamakawiwo’ole, Natalie Cole, Eva Cassidy, Anne Murray, Joey Ramone, Coldplay, Sara Brightman, Rod Stewart, Michael Buble, Celine Dion, LeAnn Rimes, and John Legend.