Several years ago I saw a country/western video sung by a male artist who was on a roof top of a downtown building. He was signing about a girl and I believe she was ignoring him. Can you please tell me the artist name and song title?

Was it "Settle For a Slowdown" by Dierks Bentley? Watch the end part

YouTube - Dierks Bentley - Settle For A Slowdown

There is another video that I can picture in my head, but can't put a face to it. It has a lot of Las Vegas looking signs, etc. One in particular is a cowboy or cowgirl with a rope, or something like that. I will keep thinking on this one!!

An older video by Randy Travis starts like that. It's "Better Class of Losers"

YouTube - Randy Travis - Better Class Of Losers

I'm not sure, but I saw a video once ny Aaron Tippin that describes what you saw. Do you remember any details on the singer?