In this song, Kid Rock raps about heading west to conquer California, envisioning himself as a trailer park cowboy riding into town with a bottle of beer and a bad attitude. He makes it clear he's no N.W.A.:
I'm not straight outta Compton, I'm straight out the trailer
The video for this song is an homage to the movie Smokey And The Bandit. Directed by Dave Meyers, it culminates in a showdown between Rock's 3'9" sidekick Joe C. (R.I.P.) and '80s television star Gary Coleman, who is also rather short. According to Coleman, Joe C. was rather pugnacious from the moment they met, telling Coleman he could beat him up in real life. Gary says he went easy on him because Joe said he had medical issues and bruised easily.
And to raise the bonkers factor even higher, adult film star Ron Jeremy appears in the video as the piano player.
One of the lines in the song is: "Start an escort service for all the right reasons." When asked what the right reasons are, Rock has said, "To get paid. To make money."
This song was a breakthrough for Kid Rock, who released his debut album on Jive Records in 1990 but was soon dropped by the label. He issued two independent albums that flopped, but built a substantial following in the Detroit area. As a rap-rocker with a white trash aesthetic who washed out of one record company, he wasn't very attractive to record labels and made no effort to get in their good graces, maintaining his I-don't-give-a-f--k attitude in his music and his personal life.
At this time, to really see what Kid Rock was about, you had to go to Detroit, where he could pack 1000+ capacity venues. After listening to one of his CDs, that's what Jason Flom, had of the Atlantic imprint Lava Records, did. Flog saw Rock work his hometown crowd into a frenzy and was convinced he could break through on a national level. Flom signed him to Lava as-is, never asking him to tone it down or change his style. His first Lava album was Devil Without a Cause, released in August 1998. It took a while, but Flom was able to get the singles "I Am the Bullgod" and "Bawitdaba" played on MTV and on some radio stations. Rock slowly built a national audience, and in July 1999, got a lot of exposure at the third Woodstock festival. "Cowboy" was released as a single and took off, getting substantial airplay on rock radio and even cracking the Hot 100 - his first appearance on that chart. The song peaked at #82 on October 30, 1999. Devil Without a Cause ended up selling over 11 million copies in America.
The "uhhh" that comes in around the 2:50 mark is a sample from the song "Different Strokes" by Syl Johnson. Gary Coleman, who appears in the video, starred in the TV series Diff'rent Strokes.
Kid Rock shared the writing credits on this song with his co-producer John Travis, and with members of his Twisted Brown Trucker Band: Matthew Shafer (Uncle Kracker) and James Trombly.