Chris Whitley - Poison Girl
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And most of the songs on this record ... absolutely underappreciated masterwork 
A lot of them are obvious ones, but I got an obscure one for ya. I wouldn't necessarily say if you like Living with the Law, you WILL like this album but I think there's very good odds. It takes a couple listens to really reveal its charms, but honestly, it is one of my favorite top-to-bottom records of all time. Like LWTL, it has this haunting and cohesive feel to it (and a fair bit of dobro guitar actually). Doubt I've ever gone 6 months since it came out in 1994 (iirc) without listening to the whole thing. I literally never get tired of this record. Every song is great.
Give it a shot. The rockers (like the first one below) need to be played loud, on a system with some bass. I give you three tracks from Mighty Joe Moon by Stockton, California's own Grant Lee Buffalo. First one is about Waco, mostly, but you kinda have to look up the lyrics to know that. Hope you like!
And yeah 
for Chris. Fuck cancer!!!
The singer Grant Lee Phillips continues to make great music to this day. This is from 8 years ago.
And this is a single from 2023 ... very much a 'Chris Whitley' sound.
But what I'm saying is, I highly advise a spin through Mighty Joe Moon, top to bottom, one session. On headphones that can do bass, or better yet, a nice hi-fi with a subwoofer. Bassist Paul Kimble (also the album's producer) plays a lot of LOW bass, and it is such a key part of the sound (esp songs 1 & 4). Of course, if you like to indulge in whatever, indulge first 
Actually I recommend 2 times in fairly close succession 
because the hooks in this album take a couple times of hearing and all of a sudden it clicks and they're like ... indelible. It's not a concept album like Dark Side, but it has a consistent feel and vibe, like something is developing at all times, like you're going somewhere, carried along by a rich tapestry of melody and instruments (the three dudes play like 15 instruments total) that regularly breaks out into stunning gothic vistas. And with a really good sound system, the overall sound of it is amazing. So, it's Dark Side-ish. But also Whitley-ish 
Love when I get to the last song on MJM, with the whole thing before being so good and it's like the simplest track, sonically, of all of them. And I end up going "damn that might be the best song on it" 
Rock of Ages, just an 'all time' closing track. MHO, anyway.
Their debut Fuzzy is also excellent, some say their best. Album 3, Copperopolis ... bit of a dud. Album 4, Jubilee is also very worthy, though a lot more polished and commercial-sounding. It has a handful of stunners (Songs 4-10 in particular are kickass), and most of the rest are at least good songs, but a lot of it has a heavy 90's alt-rock sound. Again, best song might be the last, The Shallow End.
AFA solo albums, start with Virginia Creeper, then The Narrows.
This one from Fuzzy is one my favorite songs ever, I know every word to this long-ass story off the top of my head lol. And it's pretty reminiscent of Chris to me. You have to be into listening to the 'story of a song' generally to like it though, otherwise it's a bit of a dirge. The lyrics, and the tale, are freaking greatness.