Old English sang "voice, song, art of singing; metrical composition adapted for singing, psalm, poem," from Proto-Germanic *songwho- (source also of Old Norse söngr, Norwegian song, Swedish sång, Old Saxon, Danish, Old Frisian, Old High German, German sang, Middle Dutch sanc, Dutch zang, Gothic saggws), from PIE *songwh-o- "singing, song," from *sengwh- "to sing, make an incantation" (see sing (v.)).
Phrase for a song "for a trifle, for little or nothing" is from "All's Well" III.ii.9 (the identical image, por du son, is in Old French. With a song in (one's) heart "feeling joy" is first attested 1930 in Lorenz Hart's lyric. Song and dance as a form of vaudeville act is attested from 1872; figurative sense of "rigmarole" is from 1895.
Old English -istre, from Proto-Germanic *-istrijon, feminine agent suffix used as the equivalent of masculine -ere (see -er (1)). Also used in Middle English to form nouns of action (meaning "a person who ...") without regard for gender.
The genderless agent noun use apparently was a broader application of the original feminine suffix, beginning in the north of England, but linguists disagree over whether this indicates female domination of weaving and baking trades, as represented in surnames such as Webster, Baxter, Brewster, etc. (though spinster probably carries an originally female ending). Also whitester "one who bleaches cloth;" kempster (c. 1400; Halliwell has it as kembster) "woman who cleans wool." Chaucer ("Merchant's Tale") has chidester "an angry woman." In Modern English, the suffix has been productive in forming derivative nouns (gamester, punster, rodster "angler," etc.).