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Let's attach every character in Where the Water Tastes Like Wine to their respective song, since the wiki for the game absolutely sucks. Let's get to it! I'll also be explaining why, as well as occasionally offering my opinions on the music itself if I think it's particularly noteworthy. Spoiler free, too.
Althea: Soulsucker Blues (and it's accompanying piano version, which are both bangers, by the way). She quite literally sings this to describe her life. Best song in the game, and that is in no small part because the singer is amazing. Another possibility is Tear it Down, because she also sings it, but it seems a bit too...unrelated. Besides, Soulsucker Blues fits her better.
Quinn: Howl. They have dogs. There really isn't a better way to explain it.
Little Ben: Breathe the Black. He was a coal miner turned union organizer. The song is amazing guitar work.
Fidelina: Curandera, because she is one. A curandera is essentially a healer using folk remedies. The specific connotations of a curandera are more present in traditional or older communities, where they often have spiritual/religious connections. I pretty much only know this because of Rudolfo Anaya's novel Bless Me, Ultima. And I pretty much only remember that book because it had weirdly horny children in it.
Mason: This Trench Was Dug For Me. There are two soldiers in this game, Mason and August. August is a sailor, so I doubt he would be in trenches.
August: Shining Isles of Ivory. Honestly, this is one of the weirder pieces of music in the soundtrack, and I don't actually remember hearing it during my playthrough. I just picked it because it was kind of like a pirate song.
Dupree: Read 'Em and Weep. Easy. She's a gambler, and a fast talker. I would actually like to note how good this song is. It's tied for my 2nd favorite song in the game, next to Noodle It Out. I'm actually listening to it right now as I type this.
Franklin: Miles of Smiles. Kind of just the title that gives me this. Franklin is a passenger car worker, all smiles on his face, but in misery over the ingrained racism that put him in this situation. This song is pretty good, but not quite as much as the two above.
Ray: White Rider. He's the only character with a horse, and can be found in the Southwestern portion of the U.S. It's actually not that bad of a song. The singer and tone remind me of Johnny Cash, bless his soul.
Jimmy: Dust to Dust. He's a pastor traveling, giving eulogies and sermons. Dust to dust is a line in traditional Christian eulogies. Another alternative is Tear it Down, but feels too...angry.
Dehaaya: The Road Remembers. You can definitely tell it's her song just by listening to it. Which makes me sad. Ryan Ike (the composer) was definitely trying to make a "Native American" song, but it just feels generically non-European (or generically non-Eastern American). I feel like if this was a traditional Native American song, then it could easily be one of the best in the soundtrack, but...it's frustrating. The song itself, without any context if fine, I guess.
Rocio: Root and Rise. The chord progression sounds like generic Mexican guitar music. It's good, but the character's story is far better than the music.
Bertha: From This Field I Wish To Rise, I guess? I'm scarping the bottom of the barrel here. Bertha just might not get a song. She's really generic anyways.
Shaw: Tear It Down. This is sung by Althea, but both Shaw and Althea were written by the same person (Gita Jackson), so maybe there's a connection here? I don't really have any convincing connection there other than that. These three of Bertha, Shaw, and Cassady are all really difficult to determine.
Cassady: He's the easiest of the hard ones, as I call the trio. Probably Rail Hoppin' and/or From This Field I Wish To Rise. Rail Hoppin' because of his history travelling across the country, but also This Field I Wish To Rise, because of its reflective properties? Both of these songs are really good, by the way.
Rose: At both last and least, we have Rainbow on Wheels. A terrible song for a terrible character. It's an electric guitar in the 1930s-40s. What the heck, Ryan.
Althea: Soulsucker Blues (and it's accompanying piano version, which are both bangers, by the way). She quite literally sings this to describe her life. Best song in the game, and that is in no small part because the singer is amazing. Another possibility is Tear it Down, because she also sings it, but it seems a bit too...unrelated. Besides, Soulsucker Blues fits her better.
Quinn: Howl. They have dogs. There really isn't a better way to explain it.
Little Ben: Breathe the Black. He was a coal miner turned union organizer. The song is amazing guitar work.
Fidelina: Curandera, because she is one. A curandera is essentially a healer using folk remedies. The specific connotations of a curandera are more present in traditional or older communities, where they often have spiritual/religious connections. I pretty much only know this because of Rudolfo Anaya's novel Bless Me, Ultima. And I pretty much only remember that book because it had weirdly horny children in it.
Mason: This Trench Was Dug For Me. There are two soldiers in this game, Mason and August. August is a sailor, so I doubt he would be in trenches.
August: Shining Isles of Ivory. Honestly, this is one of the weirder pieces of music in the soundtrack, and I don't actually remember hearing it during my playthrough. I just picked it because it was kind of like a pirate song.
Dupree: Read 'Em and Weep. Easy. She's a gambler, and a fast talker. I would actually like to note how good this song is. It's tied for my 2nd favorite song in the game, next to Noodle It Out. I'm actually listening to it right now as I type this.
Franklin: Miles of Smiles. Kind of just the title that gives me this. Franklin is a passenger car worker, all smiles on his face, but in misery over the ingrained racism that put him in this situation. This song is pretty good, but not quite as much as the two above.
Ray: White Rider. He's the only character with a horse, and can be found in the Southwestern portion of the U.S. It's actually not that bad of a song. The singer and tone remind me of Johnny Cash, bless his soul.
Jimmy: Dust to Dust. He's a pastor traveling, giving eulogies and sermons. Dust to dust is a line in traditional Christian eulogies. Another alternative is Tear it Down, but feels too...angry.
Dehaaya: The Road Remembers. You can definitely tell it's her song just by listening to it. Which makes me sad. Ryan Ike (the composer) was definitely trying to make a "Native American" song, but it just feels generically non-European (or generically non-Eastern American). I feel like if this was a traditional Native American song, then it could easily be one of the best in the soundtrack, but...it's frustrating. The song itself, without any context if fine, I guess.
Rocio: Root and Rise. The chord progression sounds like generic Mexican guitar music. It's good, but the character's story is far better than the music.
Bertha: From This Field I Wish To Rise, I guess? I'm scarping the bottom of the barrel here. Bertha just might not get a song. She's really generic anyways.
Shaw: Tear It Down. This is sung by Althea, but both Shaw and Althea were written by the same person (Gita Jackson), so maybe there's a connection here? I don't really have any convincing connection there other than that. These three of Bertha, Shaw, and Cassady are all really difficult to determine.
Cassady: He's the easiest of the hard ones, as I call the trio. Probably Rail Hoppin' and/or From This Field I Wish To Rise. Rail Hoppin' because of his history travelling across the country, but also This Field I Wish To Rise, because of its reflective properties? Both of these songs are really good, by the way.
Rose: At both last and least, we have Rainbow on Wheels. A terrible song for a terrible character. It's an electric guitar in the 1930s-40s. What the heck, Ryan.