The song lyrics were written by the band Van Halen, as they were asked to write a song for the 1979 movie "Over the Edge" starring Matt Dillon. The movie (and the lyrics, although more obliquely) are about bored, rebellious youth with nothing better to do than get into trouble. If you see the movie, these lyrics will make more sense. It's a great movie if you grew up in the 70s/80s you'll definitely remember some of these characters from your own life. Fun fact, after writing the song, Van Halen decided not to let the movie use it.
When Jack Frost came for christmas
With a brass monkey date
The rail-king and the scarecrow
Hopped a Florida freight
And they blew on their paper cups
And stared through the steam
Then they drank half a bottle
Of ragpicker's dream where
The whiskey keeps following
Cold pitchers of beer
Me and my associate
Like the clientele here get
The onions and the 'taters
Rib-eyes on the grill
Toothpicks and luckies
And a coffee refill as
The rail-king lay rocking
He was leaving the ground
Then he was flying like Santa Claus
Over the town where
He came to the window
Of a house by a stream
It was a family christmas
In the ragpicker's dream there
Were kids at the table
All aglow in the light
Music in the wintertime
Sure carries at night there
Was turkey and gravy
Pie and ice-cream
And gifts for each and everyone
In the ragpicker's dream where
The red-eye keeps tumbling
In our glasses of beer
Me and my associate
Like the service in here there's
A ten for your trouble
You have beautiful hair
Make the last one two doubles
It's a cold one out there where
The scarecrow and the rail-king
Have started to dance
But a nightstick and a billyclub
Won't give peace a chance here
I think they went thataways
Your song and dance team
Heading home for the holidays
With the ragpicker's dream on
His knees like a fighter
The rail-riding king
Like a sack of potatoes
Like a bull in the ring where
The scarecrow falls over
With a tear in the seam
Home for the rover
In the ragpicker's dream where
The red-eye keeps tumbling
Like tears in our beer
Me and my associate
Like the ambience here where
They cornered two castaways
In a white flashlight beam
Merry christmas and happy days
In the ragpicker's dream
With a brass monkey date
The rail-king and the scarecrow
Hopped a Florida freight
And they blew on their paper cups
And stared through the steam
Then they drank half a bottle
Of ragpicker's dream where
The whiskey keeps following
Cold pitchers of beer
Me and my associate
Like the clientele here get
The onions and the 'taters
Rib-eyes on the grill
Toothpicks and luckies
And a coffee refill as
The rail-king lay rocking
He was leaving the ground
Then he was flying like Santa Claus
Over the town where
He came to the window
Of a house by a stream
It was a family christmas
In the ragpicker's dream there
Were kids at the table
All aglow in the light
Music in the wintertime
Sure carries at night there
Was turkey and gravy
Pie and ice-cream
And gifts for each and everyone
In the ragpicker's dream where
The red-eye keeps tumbling
In our glasses of beer
Me and my associate
Like the service in here there's
A ten for your trouble
You have beautiful hair
Make the last one two doubles
It's a cold one out there where
The scarecrow and the rail-king
Have started to dance
But a nightstick and a billyclub
Won't give peace a chance here
I think they went thataways
Your song and dance team
Heading home for the holidays
With the ragpicker's dream on
His knees like a fighter
The rail-riding king
Like a sack of potatoes
Like a bull in the ring where
The scarecrow falls over
With a tear in the seam
Home for the rover
In the ragpicker's dream where
The red-eye keeps tumbling
Like tears in our beer
Me and my associate
Like the ambience here where
They cornered two castaways
In a white flashlight beam
Merry christmas and happy days
In the ragpicker's dream
Lyrics submitted by Libra
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