16 Best Bing Crosby Songs: The Greatest of a Legend

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Last updated on June 1st, 2023 at 09:29 pm

Bing Crosby was one of the most influential artists and global icons of the 20th century, producing hit song after hit song and classic film after classic film, sometimes doing both simultaneously.

Crosby recorded more than 16,000 songs throughout his half-a-century-long career, so picking the best Bing Crosby songs to listen to was challenging, but we finally landed on our 16 favorites.

Here’s our list of the 16 best Bing Crosby songs to add to your playlist.

Best Bing Crosby Songs

16. “Accentuate the Positive”

This one was a massive group effort, and that’s a positive we’ll always accentuate for this first entry on our list of the best Bing Crosby songs.

Bing Crosby was joined by The Andrews Sisters, Vic Schoen, and his Orchestra for this clever piece referencing famous Bible figures, Jonah and Noah, to prove the song’s classic point.

Thankfully, this song makes it easy to “Ac-cent-tchu-ate the positive” because there’s no negative to eliminate.

15. “Dinah”

Bing Crosby knows how to admire his woman.

“Dinah,” released in 1932, brought Crosby together with The Mills Brothers, and together they deliver a beautifully smooth performance that kicks up the beat halfway through.

14. “Don’t Fence Me In”

Bing Crosby and The Andrews Sisters didn’t waste any time recording the hit song, “Don’t Fence Me In,” taking just 30 minutes.

They still managed perfect quality as the song went on to sell more than a million copies and dominate the charts for eight long weeks.

13. “I Can’t Begin to Tell You”

Bing Crosby may not have been the first to record this song, but he is the one who made it most popular after releasing it in 1945.

“I Can’t Begin to Tell You” just joins the list of Bing Crosby songs that perfectly incorporate what it means to truly be in love with someone and to want nothing more than to be able to relay those feelings to them.

This classic hit peaked at number one on the Billboard Best Seller Chart and was charted for 17 weeks overall.

No other recording of this song has matched the success, and that’s why Bing Crosby’s is simply the best.

12. “I’ve Got a Pocketful of Dreams”

Bing Crosby reminds us that money isn’t everything in this classic tune, which he partnered with John Scott Trotter and his orchestra, and recorded for his 1983 musical comedy, Sing You, Sinners.

“I’ve Got a Pocketful of Dreams,” like a lot of our favorite Bing Crosby songs, is full of upbeat, lighthearted sentiment that makes us believe that as long as we keep holding on to our dreams, we can live in luxury, too.

11. “Pistol Packin’ Mama”

“Pistol Packin’ Mama” is a song of sweet revenge with a hint of “hillbilly honky-tonk.” The crooner embracing that whole-heartedly makes ita lot different from so many Bing Crosby songs.

The Andrew Sisters join Crosby for this Al Dexter and His Troopers cover as a man begs his wife to “lay that pistol down” after she finds him drinking and partying in a cabaret lounge.

It’s a hilarious twist on a classic country theme.

10. “True Love”

Bing Crosby teamed up with Grace Kelly to sing this classic tune written by famous songwriter Cole Porter.

The perfect love ballad was featured in their musical film High Society.

Crosby and Kelly’s voices perfectly blend on the pivotal lyrics, “But to give to you and to give to me/Love forever true.”

9. “Swinging on a Star”

With references to being a pig or a fish, this song makes us snigger, which is perhaps why it’s one of the best Bing Crosby songs.

Once again, with “Swinging on a Star,” Bing Crosby set a standard for a genre of music, in this case, pop.

Introduced in his film, Going My Way, in 1944, it earned the Academy Award for Best Original Song that same year and is still considered a top tune in American cinema by the AFI.

To think it all started with an offhand remark the singer made to his son Gary in front of songwriter Jimmy Van Heusen when he said, “If you don’t go to school, you might become a mule.”

8. “Sweet Leilani”

It won the Academy Award for Best Original Song in the 1937 film Waikiki Wedding, and we don’t have any trouble figuring out why.

Bing Crosby’s hit song, “Sweet Leilani,” is a classic Hawaiian tune that sets the standard of “easy listening,” and it’s valid.

Just listening to it, we find ourselves falling into a trance with all our worries washed away.

Sweet Leilani, you are indeed our dream come true.

7. “You Must Have Been a Beautiful Baby”

We can’t help but bop around to the crooner when he sings, “You Must Have Been a Beautiful Baby.”

It’s a song any woman would want to hear her man sing to her as he admires her breathtaking beauty.

Bing Crosby’s flawless vocals are enough to make any girl swoon over it, just as many other Bing Crosby songs do.

6. “At Your Command”

Bing Crosby is accompanied by pianist Harry Barris, his The Rhythm Boys bandmate, for this 1931 song.

“At Your Command,” for which Crosby, along with Harry Tobias, showed off his talents for lyric writing, has appeared on five of his albums over the years.

We have a feeling several people can relate to this song about a man sorrowful for his infidelity, hoping his wife will give him another chance at their love story.

5. “My Blue Heaven”

Like many Bing Crosby songs, he adds a swingin’ jazz element to this fun song, initially released by Gene Austin in 1927.

Already a popular song by the time Crosby covered it, he gives a classic rendition of the light and uplifting story about a man who is just happy in “My Blue Heaven” with his wife and baby to make the perfect family trio.

4. “Love in Bloom”

Bing Crosby and Kittle Carlisle gave us this classic love song in their 1934 film She Loves Me Not.

We’ve all been in that moment when you are at the height of falling and love and don’t know precisely what is happening.

Well, it’s “Love in Bloom.” The song was so popular it was nominated for the Academy Award for Best Song in its inaugural year.

Although it didn’t take home the title, we love it all the same, especially when paired with Crosby’s signature voice.

Thankfully, the film version wasn’t the only opportunity to hear Crosby sing the tune as he re-recorded it 20 years later for his Bing: A Musical Biography compilation album in 1954.

3. “Brother, Can You Spare a Dime?”

“Brother, Can You Spare a Dime” takes listeners back to the Great Depression (1929-1939), as composer Jay Gorney’s classic music, based on a Russian-Jewish lullaby. Yip Harbug’s lyrics combine to tell the story of the everyman of the universe during that devastating decade.

When Bing Crosby released his recording of the song, coined the anthem of the Great Depression, in 1932, it brought major popularity as it was the only song of the era that didn’t shy away from the grimmer aspects of the time.

Crosby uses his signature “phrasing” to equal out the lyrics and melody for this vital piece, originally written for the Broadway show Americana.

Even in his slightly upbeat delivery, it grabs all listeners, whether they’re a farmer, a construction worker, or a veteran, just like the man in the song.

It’s a classic that has stood the test of time, being covered by numerous artists over the years.

2. “Pennies from Heaven”

Like so many Bing Crosby songs, this great song resulted from another great movie from the famous entertainer.

“Pennies from Heaven,” introduced in 1936 in the film of the same name, features the legendary artist joining George Stoll and his orchestra for this slow classic that he turned on the warm charm for when he sang it to young Patsy in the film.

The classic song, which topped the charts for 10 weeks after it was released and earned Crosby a posthumous Grammy Hall of Fame Induction, may have later been covered by other legendary artists in their own right, like Louis Armstrong and even Frank Sinatra.

The original by our favorite crooner will always be our favorite.

1. “White Christmas”

From the moment it was released on Christmas Day 1941, Bing Crosby had millions dreaming of a “White Christmas.”

He recorded some other classic Christmas songs over the years, including “Rudolph, the Red-Nosed Reindeer” and “Jingle Bells,” but this is the best of all the holiday tunes.

We agree with the writer, Irving Berlin, with this classic Christmas song when he told his secretary, “I want you to take down a song I wrote over the weekend. Not only is it the best song I ever wrote, it’s the best song anybody ever wrote.”

Perhaps he needed to add the word “Christmas” to that last sentence, but we digress.

It certainly is the greatest of all the Bing Crosby songs, earning the singer his first Grammy Hall of Fame induction in 1974.

Not only that, but it became the best-selling song of all time after artists such as Michael Buble and Pentatonix added it to their albums of Yuletide joy, with more than 100 million copies sold.

Make no mistake, though, more than half of those sales were thanks to Crosby.

There was no other choice for the top of our list of the best Bing Crosby songs.

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