You know how some songs were just meant for rainy days? I started this list and it had a few songs with ”rain” in the title, but I thought that was kind of cheating. Leaving that out made things more interesting. This is a good mix to sit on your front porch (under cover, of course) and watch the rain as you listen to some cool tunes.
“Jane,” Ben Folds Five (The Unauthorized Biography of Reinhold Messner)
Ben has a lot of songs that could have wound up on this list, but “Jane” earns that distinction with its minor key and somewhat somber mood.
“So at Last,” Butch Walker (Letters)
Butch is singing about Southern California in this song, but there is no denying the rainy day feel of it. I’d be really surprised if Butch wasn’t in Minneapolis on a crappy day when he wrote it.
“Let It Die,” Feist (Let It Die)
The aching beauty of this song can practically inflict wounds on the human body. This is Leslie Feist at her best.
“Cold Again,” Freedy Johnston (This Perfect World)
You can almost feel the chilly air as Mr. Johnston sings about walking over the Brooklyn Bridge. You can also probably taste the half-burnt, half-frozen pretzel from a New York City street vendor.
“Flair,” Josh Rouse (Dressed Up Like Nebraska)
This album is full of up-tempo jangly acoustic rock songs. But this one is dark and somber and awesome all at the same time.
“After Tomorrow,” LUCE (LUCE)
This track is more optimistic than sad lyrically, but the overall vibe is perfect for gray skies.
“Jen Is Bringin’ the Drugs,” Margot and the Nuclear So and So’s (The Dust of Retreat)
Here is how the lyrics start: “Jen is bringin’ the drugs / She wants to get real fucked up.” I mean, it’s not a bad idea on a rainy day.
“Don’t Believe,” Marjorie Fair (Self Help Serenade)
Most of the debut album from this band has that dreamy, underwater feel to it. And it’s bordering on brilliant.
“Suburbia,” Matthew Good (Beautiful Midnight)
One of the best under-the-radar albums of the last 10 years, Matthew Good must have written this entire album when he was in a real funk. And, you know, that always makes for the best music.
“You Just Forgot,” Mindy Smith (Long Island Shores)
This one was released maybe a month ago. Being fresh in my mind may have helped the song land here, but I think maybe it will still be a great rainy day track 10 years from now. What a voice on this chick.
“You Are Mine,” Mute Math (Mute Math)
A stunning song from a stunning debut. This is movie soundtrack material.
“Things behind the Sun,” Nick Drake (Pink Moon)
Quite honestly, you could put this song on the list 15 times and forget about the other 14. But that would be way less fun.
“Salesman at the Day of the Parade,” Rogue Wave (Descended Like Vultures)
Does Sub Pop sign any acts that don’t make rainy day songs? Not really.
“God of Wine,” Third Eye Blind (Third Eye Blind)
The last four tracks on the band’s debut album are so depressing yet somehow so compelling. Pass me the bottle.
“Windmills,” Toad the Wet Sprocket (Dulcinea)
This track will make you remember why you fell in love with Toad in the first place. Glen Phillips is my freaking hero, and this incredible song is one of his best.
