Here are my thoughts about that list

:
Where Are you Now - describes exactly my question I had in my mind about this type of country song on the radio. That song sucks for the singer
Killin' Time - Clint Black has a vevo

Not the video being from like the 70's Gosh he's cute here

Oh its from 1990

The lyrics gives me I See You - Luke Bryan teas on the topic at hand.
When My Ship Comes In - This video is odd

I'm not really a fan of the song
The Shoes You're Wearing - This song is great! its the strong guitars probably which makes me like the song much more. Its such a crafty song, but obviously other songs like the first 2 are lyrically stronger.
State of Mind - This song sounds like a great song to listen to when your drifting into thoughts. I LOVE that I can relate to this song
Like The Rain - The song is crafty for the girl he's taken a liking for. Its nicer then the State of Mind song. it has a strong instrumental, that might be part of my liking for it
Nothing But The Tailights - This song is truly a

type of song, he must have done something dumb to get dumped out in the middle of nowhere to get dumped out like that

waiT, that song is regarding HIS truck

the shade of it all!
When I Said I Do - Aww this song is nice for them.....Not this being his biggest hit on the charts

this song screams MADE FOR AC RADIO. This song is only somewhat country, its just his vocals are so country...then again I stan for Luke
A Bad Goodbye - Aww this song is sad

Where was this song when I wanted a sad "country" song (the violins throw me off)
A Better Man - Woops I got distracted by the fact the wiki page says he's from Katy, Texas. Considering I like Katy and all it drifted my attention from the song.
I bolded my top 3
Why the Garth Brooks shade tho. idk how Garth got so big in country music in the 90's....