One of the first songs I co-wrote with my longtime writing partner Ronnie Jeffrey. Initially we demoed it back in the 90s, and it was updated in 2025. I wrote the words back in college during a roadtrip with my then girlfriend, Marsha.

Cheraw to Charlottesville
In my old red jeep
I stare at the headlights
While you fall asleep
I’m a long way from happy
And a long way from home
Though we ride together
We travel alone

The people who love me
Got left behind
My mother, my sister
Back in Carolina
I’m out on this highway
Feeling battered and bruised
And trying and failing
To hold on to you

Chorus:
Why do I play this game
When I don’t know the rules
Why do I play this game
When I know that I’ll lose
Charlottesville

Charlottesville to Cheraw
We’re headed back home
A thousand cars on this road
Still I feel alone
Cause you’re afraid of forever
And scared of the words
That you hear so often
But I’ve never heard

Chorus:
Why do I play this game
When I don’t know the rules
Why do I play this game
When I know that I’ll lose
Charlottesville

Bridge:
I’m not playing this game
I’m through playing the fool
For you

Chorus:
Why do I play this game
When I don’t know the rules
Why do I play this game
When I know that I’ll lose
Charlottesville

© Kent Newsome and Ronnie Jeffrey