I love this song! Of course, I think she is talking about Lindsey as "the highwayman." He is always out on the road, as is she, the "highwaywoman", and both can't seem to settle down. He "in all his glory was far ahead of her" - Stevie always thought Lindsey was a genius and, in songs like Long Distance Winner, expresses a feeling of inadequacy around him. Still, it was worth it for the "burn." However, when competition enters (Lindsey's music) she is left chasing "the moon" and feeling like a "fool." They begin to have problems and she doubts the reality of their love; he tries to suppress his love for her so it doesn't control him. The dream starts to crumble.
Lindsey won't slow down for her - he's too dedicated to his music, too eager to "win" (like in Go Insane). She uses great imagery to describe his intensity: "a pale and violent rider" whose love was a "dream begun in wine." She watches him go and is forced to wake up from the "dream" amidst the "thunder" (see Dreams). Then, there's the aftermath. They still "ride together" in FM, but can they win at love? Is there still a chance for them,=when he's so focused on "glory"? But "still they try again", they both stay in the band and deal with it. By the way, Don Henley sings backing vocals on this.
Stevie once said in an interview that this song is about all of her friends in the music buissness including Tom Petty and Don Henley and how difficult it was for them to be in love with someone and be on the road. I think that the second and fourth verses are definetly about her struggling relationship with Lindsey and about how being famous doesn't make it easy for them to be together.
This has always been one of the best Stevie songs in my opinion. I feel it isnt so much about her loves as much as about how it is hard to be loved. She is always on tour and can never find Mr. Right, there are always problems. I think if she never became famous her and Lindsey would have stayed together been happy. She went for the glory and lost the love
Will they ever win?
He the glory...
She the love...
Still they try again
She isnt willing to give up on love but she doesnt really see it working out in the long run unless something changes.
Want to speculate about "The Highwayman"? E-mail me and I'll post your comments.