Meaning Behind Kid Rock’s Breakthrough Hit “Cowboy”

Following the release of Kid Rock‘s first three albums and the further development of his trailer-park pimp persona, “Cowboy,” off his fourth album Devil Without a Cause, was his first single to hit the Billboard Hot 100. The song peaked at No. 82 on the Hot 100 in 1999 and would also peak at No. 10 on the Mainstream Rock Airplay chart. 

The country rap-rock song was Rock’s breakthrough hit. Below, we uncover the meaning behind “Cowboy.”

The Meaning: Booze, Women, and Trouble

The mission: move from living in trailers to something more palatial in the Hollywood Hills, buy a yacht, have plenty of scotch (and Beck’s and Boone’s Wine), and women galore.

Well, I’m packin’ up my game an’ I’m a head out west
Where real women come equipped with scripts an’ fake breasts
Find a nest in the hills, chill like Flint
Buy an old drop top, find a spot to pimp

An’ I’m a Kid Rock it up an’ down your block
With a bottle of scotch an’ watch lots of crotch
Buy yacht with a flag sayin’ ‘Chillin’ the most’
Then rock that bitch up an’ down the coast

A picture-perfect day in the life, “Cowboy” is Rock’s anthem for living the life, as crudely as he desires. In all its salacious detail, Rock envisions himself as a trailer park cowboy riding into Los Angeles and taking over, starting an escort service inspired by Heidi Fleiss — and getting into more trouble along the way.

Give a toast to the sun, drink with the stars
Get thrown in the mix an’ tossed out of bars
Zip to Tijuana, I wanna roam
Find Motown an’ tell them fools to come back home

Start an escort service for all the right reasons
An’ set up shop at the top of Four Seasons
Kid Rock an’ I’m the ‘Real McCoy’
An’ I’m headin’ out west, sucker because I wanna be a

Cowboy, baby
With the top let back an’ the sunshine shinin’
Cowboy, baby
West coast chillin’ with the Boone’s Wine

Detroit, Not Compton

More scenarios unfold as he bulldozes into town — most censored by radio — while referencing his Detroit roots. He makes it clear he’s not from Compton, Los Angeles.

Cause chaos, rock like Amadeus
Find West Coast pussy for my Detroit players
Mack like mayors, ball like Lakers
They told us to leave but bet they can’t make us

Why they wanna pick on me?
Lock me up an’ snort away my key
I ain’t no G, I’m just a regular failure
I ain’t straight outta Compton, I’m straight out the trailer

Cuss like a sailor, drink like a Mick
My only words of wisdom are just, Radio edit
I’m flickin’ my Bic up an’ down that coast
An’ keep on truckin’ until it falls into motion

Gary Coleman and Ron Jeremy

The music video for “Cowboy,” directed by Dave Meyers, lives up to its lyrics, showing Rock on his journey out West with his crew.

Guests in the video include the late Gary Coleman, best known for playing Arnold in the 1980s hit TV sitcom Diff’rent Strokes, and porn star Ron Jeremy. Rock’s former 3’9″ sidekick Joe C also stars in a sepia-toned, Western-style fight scene, and the video continues with Rock and his entourage getting chased by a town sheriff, who he calls a “pig.”

Cowboy
With the top let back an’ the sunshine shinin’
Cowboy
Spend all my time at Hollywood an’ Vine

Cowboy
Ridin’ at night ’cause I sleep all day
Cowboy
I can smell a pig from a mile away

Cowboy
With the top let back an’ the sunshine shinin’
Cowboy
With the top let back an’ the sunshine shinin’

Spurred by “Cowboy” and other hit single “Bawitdaba,” Devil Without a Cause was a major commercial success for Rock and sold more than 14 million copies.

Photo: Scott Legato/Getty Images