Turn out the Lights. Start there.
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Really depends what you're looking for.
Thompson is a terrific songwriter who has two styles; character driven narratives (you might particularly seek out his more recent work - back to "Rumour and Sigh") versus personal revelation (more often with Linda - See "Shoot Out The Lights").
He's a wonderful acoustic player (Vincent and Beeswing are his two best known ballads) and a monster electric guitarist (Shoot Out The Lights, Cavalry Cross, Sloth, etc, etc.)
I'd definitely start with "Watching The Dark". It's a great intro to most aspects of Thompson's repertoire.
Yes, "watching the dark" would be excellent, a wonderful 3cd set. If that hooks you, then you've got much to look forward to, all the solo albums, duos with linda, and the great early fairport convention stuff, and maybe even all the albums he's played lead on.
I like early Bruce Cockburn, but can no longer get on with him. He's such an ass of a person, that I can't get past that. A friend in the business told me years ago there are many greats that you wouldn't want to hang with, and he's one of them.
You might also try Martin Simpson, especially his latest, "prodigal son".
A couple more thoughts:
For sound quality, you may want to look for the Mitchell Froom productions.
These aren't necessarily "audiophile" recordings, but they are
generally good recordings of vocal/guitar surrounded by lots of stuff that
"enhances" the main ingredients. Unfortunately, this was a
relatively brief period (see "Action Packed", a Capitol Records
greatest hits collection) where RT made very good music, but it misses much
of the variety that makes his catalog so wonderful.
Also, RT is, as much as almost anyone I can think of, all about live
performance. His website offers many live cds, any of which will be
worthwhile. My personal favorite is "Two Letter Words" and I'd
highly recommend it.
Finally, listen carefully to some of the lyrics on those early records. Songs like
"Dimming of The Day" and "Walking on A Wire";("Where's the justice, where's
the sense, when all the pain's on my side of the fence?") . Then check out
the more recent stuff like "Guns Are The Tongues" , "I Feel So Good" ,
"Waltzing's For Dreamers" , etc. You really get a sense of just how broad RT's
lyrical ability is.
One of my favorite Richard Thompson CDs is "King Of Bohemia" - a very rare live recording from 1991 consisting of eight songs recorded at the KPFK studios in LA, and nine songs recorded at The Ventura Theater in Ventura, CA. If you find a copy, BUY IT! It's a great introduction to RT's work, and sounds quite good as well. The number is EMCD12. No other info is given on the CD.
Also, you might want to pick up a CD or two by Luka Bloom, particularly "Riverside" and "The Acoustic Motorbike." Both really outstanding songwriting and guitar work. One of the best percussive rhythm guitar players on the planet.
As for Bruce Cockburn, make sure you try two of my favorites, "Breakfast In New Orleans Dinner in Timbuktu" and "Dart To The Heart." Both boast some of his best songs, IMHO.
The old kit bag, Richard in guitar form. He is the best guitarist. At least, his solos are always interesting, different from other players, never boring. Plus he is a great vocalist. Buy the albums not compilations. The one with Bathsheba is probably his best album, beside shoot out the lights with his ex Linda Thompson. Nothing he has put out is bad.