I assure you, it is Ken Coomer; I live in the Belleville/St. Louis area and followed UT closely back then--seeing them in bars. Jay Bennett was never in Uncle Tupelo. Yes, I see the resemblence with the curly hair and all, but it is not Jay. To see a picture of the 2 of them in Wilco, google search "chicago magazine coomer"-- click on the 1st link to chicago magazine--it's an article about Jay--it shows them together and you can see that it is Coomer in this Conan video of Uncle Tupelo.
If you heard Uncle Tupelo was an alt country band, and this was all you ever heard/saw of them, you'd probably think, "Huh. These guys sound more like a Noise Band." Love the rawness shown here.
This is my favorite of the UT, W, SV canon. Has everything I love: rock, melody, & punny logic. I'd been taking long cuts for years before I heard the song. I was lucky enough to stumble into Wilco, then UT, then Son Volt so I didn't have to choose a side. I knew OF them but I didn't take the time to realize that this was MY music. You'd have thunk that years of loving The Replacements I would have accidentally heard them but, nope.
Chiming in with a few relevant quips: The Heidorns were my neighbors, on Anna Ln. in Swansea, IL and I was friends with Suzie Heidorn, Mike Heidorn's little sister. For those who don't know, Mike was the Orig Drummer for UT. I got to sit in on quite a few rehearsals in the mid 80s when I was about 7-11, in the Heidorn's basement while Suzie and I ate a stupid amount of popcicles. Anodyne came out when I was about to graduate from Belleville West. Saw the original UT only once at Mississippi Nights in '90. They were great. I also got to interview Jay about 20 years ago when Son Volt released 'Okemah and the Melody of Riot.'