A Midnight Jamboree with the Headless Horseman

In the annals of American entertainment, few names have achieved the stature of Bing Crosby. His smooth, baritone voice always sounded effortless, bringing a casual charm to everything he sang. Over the course of his career, he had close to 400 charting singles, with approximately 41 achieving reaching number one. Four performances (White Christmas, Swinging on a Star, Pennies from Heaven, and Don’t Fence Me In) have been inducted into the Grammy Hall of Fame, and by some estimates has sold as many as 500 million records. Fourteen of his songs were nominated for Academy Awards, including four wins.

But his talents didn’t end with music. Crosby appeared in 70 films, including the popular “Road To…” series with Bob Hope. He won the Academy Award for Best Actor for his performance as Father Charles “Chuck” O’Malley in Going My Way, and was nominated for his reprisal of the role in The Bells of St. Mary’s.

Despite such a prolific career, his only Disney credit came with the release of 1949’s The Adventures of Ichabod and Mr. Toad, based upon The Legend of Sleepy Hollow from Washington Irvin’s book The Sketchbook of Geoffrey Crayon, Gent. and The Wind in the Willows by Kenneth Grahame. Crosby provided the narration for the Sleepy Hollow segment, as well as voicing the characters of Ichabod Crane and Brom Bones.

In the film, Crosby performs the song Headless Horseman, which tells of the haunts that come to the village of  Sleepy Hollow on Halloween. The most frightening of all is the Headless Horseman, who has grown “tired of his flamin’ top” and has “got a yen to make a swap. So he rides one night each year to find a head in the Hollow here.”

The song itself was composed by the successful songwriting duo of Don Raye and Gene de Paul.

The Boogie Woogie Vaudeville Boy

A member of the Songwriters Hall of Fame, Don Raye was born in Washington D.C. on March 16, 1909. He earned his chops touring Europe and the United States on the vaudeville circuit. As noted in his bio on Shazam, “After starting to write songs to liven up his act, Raye realized that his work was not only good enough to sell to others, but that this might constitute a better living than the vaudeville stage…In the mid-’30s, he was collaborating with Sammy Cahn and Saul Chaplin, as well as bandleader Jimmie Lunceford, and had developed a swinging style as a songwriter. Among his early hits was “Down the Road a Piece,” a neat little amalgam of bluesy rhythm and vivid, catchy lyrics that was picked up by Freddie Slack and Will Bradley, and covered by everyone from Glenn Miller to Count Basie.”

Raye had a gift for incorporating things like slang into his lyrics, such as in his hit Beat Me Daddy, To the Eight Bar, first recorded by Will Bradley and His Orchestra, and then by the Andrews Sisters, both in 1940. The latter group would immortalize his biggest hit, The Boogie Woogie Bugle Boy a year later as part of the Abbott and Costello film Buck Privates.

He continued writing music for films, and began collaborating with Gene de Paul. 

Writing Singy Kind of Songs

A decade younger than Raye, Gene de Paul was born in New York City and trained as a classical pianist. Like Raye, he served in the United States Army during World War II. Later in his career, he wrote music for Sesame Street (such as A Singy Kind of Song), but would write a number of hits in the 1940s, including You Don’t Know What Love Is, and the Academy Award nominated Pig Foot Pete

In the 1950s, he teamed up with Johnny Mercer to write the music for Seven Brides for Seven Brothers, and the duo would later combine their talents on Broadway for the musical L’il Abner. But before that, he was a frequent collaborator with Raye. 

In 1941, the pair wrote Cow Cow Boogie (Cuma-Ti-Yi-Yi-Ay) for Abbott and Costello’s Ride ‘Em Cowboy, which would become a hit for Ella Fitzgerald and the Inkspots. They also wrote I’ll Remember April (featured in the same film) which became a hit for Chet Baker, Bing Crosby, Bobby Darrin, and others. 

In the early part of the decade, Disney began their work on a possible feature film of The Legend of Sleepy Hollow, which was interrupted by the outbreak of war. As Jim Korkis wrote on Cartoon Reasearch, “After the war in late 1947, the studio was still financially struggling so Walt decided to pair the story with another adaptation being developed, The Wind in the Willows, as his final package feature. The Adventures of Ichabod and Mr. Toad was released October 5th, 1949.”

Raye and de Paul were brought on to write music for the film, having contributed to 1948’s Disney film So Dear to My Heart. Early on, voice actor Thurl Ravenscroft was considered to sing Headless Horseman, and Disney would later release a record of him performing the piece. However, Bing Crosby had been brought onto the project (along with Basil Rathbone for the Wind in the Willows segment) to help ensure the film’s financial success, and it was determined that for consistency Crosby would provide all of the vocal parts for the Sleepy Hollow segment (except for those of the female characters). 

Bingo from Bingville

Hailing from Tacoma, Washington,  Harry Lillis Crosby, Jr. earned his lifelong nickname as a child. A fan of the comicstrip The Bingville Bugle, Crosby was known to giggle uncontrollably while reading it, which lead a neighbor to dub him “Bingo from Bingville.” Eventually, it would be shortened to just “Bing,” a moniker which would become a household name worldwide. 

This story was later confirmed as fact, but was not the initial tale Bing told to a curious Joan Blondell in 1937. At the time, he related, “”Well, I’ll tell you, back in the knee-britches day, when I was a wee little tyke, a mere broth of a lad, as we say in Spokane, I used to totter around the streets, with a gun on each hip, my favorite after school pastime was a game known as “Cops and Robbers”, I didn’t care which side I was on, when a cop or robber came into view, I would haul out my trusty six-shooters, made of wood, and loudly exclaim bing! bing!, as my luckless victim fell clutching his side, I would shout bing! bing!, and I would let him have it again, and then as his friends came to his rescue, shooting as they came, I would shout bing! bing! bing! bing! bing! bing! bing! bing!” 

An enormous fan of singer and actor Al Jolson, Crosby first got an up close look at the legendary performer as a prop boy at the Auditorium Theater in Spokane, Washington. Years later, the two would perform together on a memorable duet of Irving Berlin’s classic Alexander’s Ragtime Band

He began performing in groups around Spokane, and according to a Mental Floss article, managed to become a huge success twice. They wrote, “…he and partner Al Rinker cut out for California to try to make it big in Hollywood in 1925. Rinker was the brother of jazz singer Mildred Bailey, who set him and Crosby up with some connections, and they were soon performing as part of a revue called The Syncopation Idea. Their talent was spotted there by the incredibly popular king of jazz, Paul Whiteman, who hired them. They had been in Los Angeles less than a year. When overnight success struck again for Crosby, it was after he decided to get serious as a solo act. He debuted on national radio September 2, 1931, and had 10 of the top 50 songs of that year.”

Volumes could be written about Crosby’s life and career (and indeed have been), but it is enough to note that there are few performers who match the stature and worldwide reach that his career achieved. The song White Christmas alone would have been enough to secure his place in the great pantheon of entertainment history. It’s to all of our benefit that he did so much more, including bringing life to one of Disney’s spookiest songs.

The year The Adventures of Ichabod and Mr. Toad was released, Crosby would release a 10” record of Headless Horseman. As we venture further into the October Country, I’ll leave you with the lyrics as Crosby performed them.

Now gather ’round

While I elucidate

On what happens outside when it gets late.

’Long about midnight

The ghosts and banshees

Get together for their nightly jamboree.

There’s ghosts with horns and saucer eyes

And some with fangs about this size,

Some short and fat,

Some tall and thin.

Some don’t even bother to wear their skin!

Ho ho! I’m tellin’ you, brother:

It’s a frightful sight

To see what goes on in the night!

When the spooks have a midnight jamboree,

They break it up with fiendish glee.

Ghosts are bad, but the one that’s cursed

Is the Headless Horseman: he’s the worst.

When he goes a-joggin’ ‘cross the land

Holdin’ a noggin in his hand,

Demons take one look and groan

And hit the road for parts unknown,

And there’s no wraith like a spook that’s spurned.

They don’t like him and he’s really burned!

He swears to the longest day he’s dead

That he’ll show them that he can get a head!

So close all the windows,

Lock the doors;

Unless you’re careful, he’ll get yours.

Don’t think he’ll hesitate a bit

’Cause he’ll clip your top if it’ll fit,

And he likes them little, likes them big,

Part in the middle or a wig,

Black or white or even red:

The Headless Horseman needs a head!

With a hip-hip and a clippity-clop,

He’s out lookin’ for a top to chop,

So don’t stop to figure out a plan:

You can’t reason with a headless man!

So after dark, you kids be good!

Stay at home, the way that you should,

‘Cause right outside, and waitin’ there,

Is the Headless Horseman. Beware!

Man, I’m gettin’ outta here!


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