
Sometimes life just rains on your parade (or Farmers Market, in my case), and sometimes the best thing to do is just let it happen. And an easy way to revel in a rainy day is some good rainy day music. Because, let’s be honest, nobody feels like listening to Pheonix on those blue, rainy days. These days call for something special, something down and out, something low-key, something sad. Here’s a good place to start, and just remember too much rainy day music on a sunny day just isn’t healthy. So sit down with a good book, cancel your trip to the beach and listen to these high lonesome sounds|
10. 3rd Planet | Modest Mouse
Modest Mouse are masters of melancholy, the majority of their (earlier) music seems to have the heartache of their generation on its back. This song starts off with a low-key melancholy, and as it progresses and picks up in tempo and volume, the music keeps the original feel of sadness. One of my favorite MM songs off of the pretty good album “The Moon & Antarctica”. I especially enjoy this live version from Austin City Limits.
9. Sister | Sufjan Stevens
Off of his masterpiece, “Seven Swans”, this song is sprawling and pretty. The soothing electric guitar, lack of vocals for 85% of the track and signature Sufjan backup vocals make this a song that promotes serious rainy-day introspection. It’s somewhat lonely yet somewhat hopeful. This is a rare track that can double as a sunny day, windows down song because it sort of adapts to its atmosphere. Yet the low, soft, poetic vocals that sort of come out nowhere bring the sadness. I mean seriously “what the water wants is hurricanes, and sailboats to ride on its back” sung by Sufjan; that will set the rainy-day mood real fast.
8. Moonshiner | Uncle Tupelo
Alt-Country artists know how to make sad songs, and so it figures that the fathers of Alt-Country could make a track this down-and-out. You can hear the longing in Jay Farrar’s voice and can empathize with his brokenness. A cover of the legendary folk song from the 1930′s, “Moonshiner” has been recorded by giants such as Bob Dylan, Elliott Smith and others, but none have captured the rainy day sound like the boys from Belleville, Illinois
7. Impossible Germany | Wilco
There is so much I could say about this song. The vocals, the guitar, the freaking guitar, the lyrics, all blend together to make this one of the most introspective, powerful songs in Wilco’s vastly introspective, low-key indie rock catalog. Also, just a note, Nels Cline’s guitar solo is my favorite guitar solo of all time, it actually gives me goosebumps every single time I hear it. This song reminds me why Wilco is my favorite band.
6. Oliver James | Fleet Foxes
The Fleet Foxes, despite being a relatively new band, have the soul of many an old-timey folk singer before them. Their songs conjure up beautiful and emotional imagery. Sometimes their songs are somewhat cheery, or at least take you to somewhere quite pleasant. But “Oliver James” is a bit different, it is still pleasant, but the sadness in the air is unescapable, and for some reason you don’t want to escape it, but simmer in it. It is a song that lends itself to silence after listening (which is probably why it is the last track on the CD) because it gradually takes you into silence, and subsequently, introspection.
5. Devil Got My Woman | Skip James
Nothing is more melancholy than the blues, and nobody is more blues than the great Skip James. This is the flagship Skip James song, first recorded in the late 20′s, and again upon Jame’s rediscovery in the late 60′s. This track reeks of hard times, and sings of living a life conducive to melancholy in the Old South. This song isn’t dark at all, but gritty and lonesome. It’s hard to put a finger on the Delta Blues, and the only way to really understand it is to listen to it.
4. Angel Band | Ralph Stanley
Ralph Stanley is a bluegrass legend, actually no, he is just an overall legend. His voice is literally chilling and his old timey spirituals are beautiful. Stanley’s voice can make me cry almost every time I listen to it. It really is that high and lonesome sound.
3. Jacksonville Skyline | Whiskeytown
Americana is sort of the rain-day genre in my book. The sound is lonesome and down-to earth and the instrumentation is emotion inducing. I love everything (for the most part) that Ryan Adams comes out with, and he is a modern-day master of melancholy in the footsteps of greats like Hank Williams, Buck Owens and Johnny Cash. This is an early Adams track off of “Pneumonia” (2001) but stays a personal favorite sad country song.
2. Sinnerman | 16 Horsepower
Another cover of a classic folk spiritual (there’s some real melancholy in those old tunes) that just brings the rain clouds with it (as any song called ‘Sinnerman’ appropriately should…). This is overall just a wonderful song, thanks to the ridiculously talented David Eugene Edwards.
1. Christmas Day | Jim White
Jim White is A.) one of the best kept secrets in music and B.) one of the best storytellers in all of Americana music. This song is straight up sad. It’s a sprawling epic in the traditional sense, detailing the unlikely reopening of a wound supposedly healed. This song carries some personal circumstantial weight for me, but all of that aside, it is my definition of rainy day music. Allow yourself the time to invest in this song, like a good novel, and you’ll get what White is trying to convey; possibly at a level that is uncomfortable and sorrowful
note: It was difficult cutting this list down to only 10, feel free to link and suggest others that I missed. I know I left out some great/sad stuff.


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