Rain by the Beatles comes to mind first, with John's acerbic commentary and Paul's high bass part. Sweet pre-Pepper Fab Four.
Listen to the Rhythm of the Falling Rain.... by the Cascades--a pretty early sixties song of regret that still gets a lot of (oldies station) airplay.
How I Wish it Would Rain by the Temptations is the old story about how men aren't supposed to cry so to avoid cabin fever, the poor guy wishes it would rain so no one would see his tears when he goes outside.
Who'll Stop the Rain by Creedence Clearwater Revival. Long as he remembers the rain's been pouring down. With John Fogerty it's all symbolic too, of course. It was the late 1960's--nuff said.
The Rain, the Park and Other Things by the Cowsills is a soft psychedelic song by the talented but pop-oriented family group. I loved it, but the "I knew I knew I knew I knew" part was a little annoying.
Box of Rain by the Grateful Dead. I really like this song but don't really understand it. I heard that Phil Lesh wrote it for his dad. It's one of the rare Dead songs by Phil with him singing lead. This link goes to a much later live performance. Oh--I forgot--Happy Birthday Phil! (3/15).
Yellow Balloon by Yellow Balloon. I love this little 1967 pop hit by the mysterious one hit wonders. It contains "it's raining it's pouring" in the middle. With the vocal harmonies and meter changes, it sounds like Brian Wilson could have written and produced it.
There are many more. How about Don't Let the Rain Come Down by the Serendipity Singers? Group folk music at it's most poppy.
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