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WEBMISTRESS speculates:
This very sobering song is obviously about death, specifically the death of Lindsey's father. Lindsey's lonely and afraid on the "street of dreams", which I believe is a metaphor for life and the journeys one takes in order to follow his dreams. But it can be a hard journey, full of people trying to "sell" something and a lot of loneliness. Then Lindsey gets to the heart of the matter: he misses his father and it's cast a shadow over his life - the "shadow on daddy's stone" over his father's grave. The death of his father has raised several questions for him - does his life mean anything, or is it just dreams and tests?
His life is full of difficulties and he wonders if he'll ever have peace, if he'll "ever make it home again." It's been over ten years, and he still doesn't have it. Will he ever stop having those nightmares? The answer is no. (An alternate meaning could be that he's asking if he'll lose his ability to have dreams to follow, and the "never" is encouragement). Finally, he's "praying" for someone to be with him, to stay with him, on this "lonely, lonely, lonely, lonely street of dreams."
DW speculates:
Fear can be paralyzing and the constant intrusion of people "selling" empty promises (especially in the rough and shallow world of "showbiz") leaves one feeling lost and abused sometimes. I agree that the song is both about missing his father and the loneliness and difficulty of life's path. The two feelings feed each other and Lindsey actually talks to his dad (in spirit), searching for guidance and maybe some reassurance.Lindsey did say that he goes to visit his father's grave and talks to him and tries to imagine what his father would say to him when he needs to sort out things that are on his mind. His father seems to represent a figure of unconditional love to whom Lindsey can always turn with any problem.
I think the "shadow on daddy's stone where he was laid to rest" is quite literal. The shadow is Lindsey, I think. It's the shadow he casts on his father's grave stone when he goes up to visit the grave sight. Lindsey "turns his back against the cold (the outside world), and turns his "face into the wind" (the dreamlike state, the imaginary state in which he can talk to his dad). He asks, "will I ever stop dreaming dreams?" I think the answer from his dad, and actually from deep inside Lindsey's heart, is meant as an encouragement. Lindsey's dreams haven't always worked out and life has been heartbreaking sometimes, so the "dreams" almost seem like the source of his problems. Without those dreams to drive him, Lindsey maybe imagines his life could be easier. But in actuality, it's the dreams that keep him going. It's the musical visions and ideals that keep him most alive, and are his gift. The response from his dad to the question is "never, never, never" give up your dreams. With the final verse, Lindsey's still lonely and afraid, but it's clear that he's decided to stay on this street of dreams (though he wishes "you" (dad?) would "be staying" with him).