The Beatles - Dear PrudenceThe sun is up, the sky is blue, it's beautiful and so are you. This song was written by John Lennon while the Beatles were studying Transcendental Meditation in India with the Maharishi Mahesh Yogi. It appears on the Beatles 1968 album
The Beatles (a/k/a The White Album). The Prudence in the song is the sister of actress Mia Farrow. Both were on the trip to India with The Beatles, which also included people like Donovan and Mike Love. Prudence immersed herself so totally in meditation, that she locked herself in her room for hours "trying to reach God quicker than anyone else", meditating alone. Concerned about her, John and George were enlisted to draw her out of her room and back out amongst everyone again, so they did so by singing her this song. The finger picking guitar technique used by John in the song was taught to him by Donovan.
Runners up:
Layla (Derek and the Dominoes). I'll say one thing. Pattie Boyd was a lucky woman to have such beautiful songs written for her. This one, by Eric Clapton (who also wrote "Wonderful Tonight" for her), and George Harrison's "Something".
Angie (The Rolling Stones). A big assumption made about this song was that it was written by Mick Jagger about David Bowie's then wife Angela, who supposedly walked in on Jagger in bed with her husband, a story Jagger denies. Here's what Mick says about the song: "People began to say that song was written about David Bowie's wife but the truth is that Keith wrote the title. He said, 'Angie,' and I think it was to do with his daughter. She's called Angela. And then I just wrote the rest of it."
Vincent (Don McLean). This song and its imagery reflect the life, death, and work of the artist Vincent Van Gogh. The prominent painting in this song is "Starry Night", a piece that Van Gogh painted after having committed himself to an asylum. Not able to see the night while committed, he painted the starry night sky from memory. It's a touching and beautiful song that always brings my emotions to the surface.
Eleanor Rigby (The Beatles). Ah, look at all the lonely people... Not much needs to be said about this song, it just captures the feeling of the people it invokes (Eleanor, Father McKenzie). The string section weeps. There are other name songs from the Beatles, I'm sure you can pick them out, so I'll leave it with Prudence and Eleanor.
Daniel (Elton John). I'll let the song's writer, Bernie Taupin, explain: "I'd seen this article in Time magazine on the Tet Offensive. And there was a sidebar next to it with a story about how many of the soldiers that were coming back from 'Nam were these simple sort of down home country guys who were generally embarrassed by both the adulation and, depending on what part of the country you came from, the animosity that they were greeted by. For the most part, they just wanted to get back to a normal life, but found it hard, what with all the looky loos and the monkeys of war that they carried on their backs. I just took it from there and wrote it from a younger brother's perspective; made him disabled and wanting to get away. I made it Spain, basically, because it rhymes with plane."
Cecilia (Simon & Garfunkel). Not much should be read into this one. As Paul Simon explained to Rolling Stone Magazine: "Every day I'd come back from the studio, working on whatever we were working on, and I'd play this pounding thing. So then I said, 'Let's make a record out of that.' So we copied it over and extended it double the amount, so now we have three minutes of track, and the track is great. So now I pick up the guitar and I start to go, 'Well, this will be like the guitar part' - dung chicka dung chicka dung, and lyrics were virtually the first lines I said: 'You're breakin' my heart, I'm down on my knees.' They're not lines at all, but it was right for that song, and I like that. It was like a little piece of magical fluff, but it works."
I know there are many more, but I'll leave it here.