Lyric discussion by Dorfkrug 

Cover art for The Last Laugh lyrics by Mark Knopfler

I think this song talks about the persevering journey to success.

Also, I found something in these lines:

"Out on the highway with the road gang working Up on the mountain with the cold wind blowing"

I think they refer to Daniel Boone, motivating his team to get through the forests in the Cumberland gap when they were trying to move west.

My Opinion

It s obviously biographical, how life on the road must be, these artists did America and paid his dues.