Eels - "Railroad Man", "The Other Shoe"
This one two combo was the first that popped into my mind. "Railroad Man" is all about how a man feels when he can't relate to the people around him or the life that they lead. It's a personal favorite of mine, as I can relate to sometimes feeling like everyone around me is living lives that are exciting or successful. It is also about contentment with yourself, which I really admire about the lyrics. They are smart and deep, while also being accessible and singable. And the instrumental backing is like the Piano coda in "Layla", being pure musical bliss with some very emotive slide guitar. "The Other Shoe" follows that up with a much darker and rebellious feel. It explores similar territory, however, and runs parallel with Dylan's "Like a Rolling Stone", in that it expresses the warning against pride and decadence. Plus, E explodes in high-pitched hoots towards the climax of the song. And I'm a sucker for explosions of emotion in music.
The Kinks - "Some Mother's Son", "Drivin'"
Part of their "Arthur" concept album, "Some Mother's Son" and "Drivin'" are a perfect contrast to each other. "Some Mother's Son" is a stirring song about war and death and memories and family. It explores the instinctual emotions that a son has for his mother and a mother for her son. A fantasticly written song with lyrics that couldn't be much better, it is a rather depressing and somber tune. Follow that with "Drivin'" a happy ditty about forgetting one's worries and taking the car out with some friends to enjoy the countryside. It plays beautifully after "Some Mother's Son", as it actually contains a subtle reference to war. This adds a dynamic tension to the song that would be lost if the songs were not played together. It would just be about driving instead of being about temporal distractions, universal truths of life and death, class differences, and ignorance.
Bruce Springsteen - "State Trooper", "Used Cars"
I couldn't find a clip of "Used Cars", but Youtube it and there're a few decent covers.
Originally split to sides A and B, "State Trooper" and "Used Cars" are exemplary together. While it may make more sense to try and pair "Highway Patrolman" and "State Trooper", since they are linked by the same themes of regret, law, and pursuit, while also being two opposite viewpoints on either side of the law, I think "Used Cars" really fits well with "State Trooper". "State Trooper" is about a man who has lived his whole life in regret and on the run, trying to forget the things that he's done while also getting away with his transgressions. It ends with some hoots. I love hoots. Especially surprise hoots that Bruce pushes out with great force. "Used Cars" is about a boy, or young man, who promises himself that he will never have to buy a used car when he grows up. There's a beautiful balance of pride and shame towards his family and you can see the repurcussions of being an outsider among more successful folks. Played together you have two stories that could work as one. A tremendously American album, "Nebraska" should be owned by every redblooded American.
So, there's three collections of songs that I love and find to be best when played side by side. What sort of songs do you think work the best together?