El Mel: Well, I hate to pile on here. I'll start off by saying that in general I'm just not a fan of the era and genre that's been highlighted, but this only applies to the first half of the list approximately.
There were a fair number of songs I was familiar with that I already enjoyed, but I have to agree with IWB in that at times it seemed like a very cliche 80s collection: I Melt With You, More Than This, Bette Davis Eyes, Love Will Tear Us Apart...these are all beyond overplayed. Surprised you didn't throw Tainted Love in there for good measure. And it's odd because with some well-known artists you went a little deeper with less-obvious tracks (Simple Minds, Til Tuesday, OMD, Tears For Fears), and I wish you had done the same with Roxy Music or Pet Shop Boys or Kate Bush.
Now having said all that, I really dug this from The DBs onward, because even with the bands I knew I hadn't heard these particular songs (R.E.M. and Shuttlecock excepted, obvs). I wasn't familiar at all with The Bats, Close Lobsters, Felt, The Chills, Prefab Sprout, and you've given me a lot to explore. And with The Association, you've given me something to definitely avoid! Though you knew that one would be divisive.
So a mixed bag for me in terms of the familiarity and just not being too into the 80s synth pop section, but I can still praise the sonic organization and transitions, which you obviously have become quite the pro at.
Gump: A nice change of pace from the usual lists, and this genre is something that doesn't get featured too often. Aside from Bright Eyes, who I've never been able to stand due to Conor Oberst's voice, there was nothing on here I actively disliked. The homogenous nature did threaten to wear out its welcome, and I think had you stretched this list even to the 90 minute mark this might have been a problem.
One major issue I have, though, is the overuse of Tweedy/Wilco. My previous jokes on the forum aside, I do for the most part enjoy the band. But putting a Wilco, Golden Smog (with Tweedy lead vocal), and Billy Bragg/Wilco collaboration on the same list doesn't seem in keeping with the spirit of the one song per artist rule, even if it's a loophole. And regardless I think Wilco and Billy Bragg/Wilco is a violation anyway.
I liked all three of these songs so it's not a quality issue, but I wish you had spread this out to more artists. You also double up on Jay Farrar with both Son Volt and Uncle Tupelo tracks and Ryan Adams with his solo work and Whiskeytown. So you essentially have three artists making up almost half of your tracks.
An enjoyable, well-organized listen despite these points of contention. The Drive-By Truckers track was a great discovery, aside from The Bottle Rockets the only artist here I wasn't familiar with.