song from the early 2000's - middle-aged white guy




My boyfriend has been trying to figure out what song this was for.. years. I am normally really good at finding things from his vague descriptions, but I am at a loss with this one!

He says he remembers listening to it as a teenager, so probably between 1999-2005 somewhere.
The music video is what he remembers the most about. He says it was black and white (or possibly just washed out/sepia toned or something), and the singer is a middle-aged white guy. He starts out singing sitting down, then gets up and starts walking through hallways that are either backstage somewhere, or maybe back hallways in a bar or something.
He can't remember anything about the lyrics, except that it had to do with a waitress, maybe a suitcase, and something about cigarettes.

The song is kind of a medium paced light rock song? or alt rock maybe

that's all he can give me, I would be amazed if any of you know what it is!

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