送别曲调取自约翰·P·奥德威John Pond Ordway(1824-1880)作曲的美国歌曲《梦见家和母亲》。《梦见家和母亲》是首“艺人歌曲”，这种歌曲19世纪后期盛行于美国，由涂黑了脸扮演黑人的白人演员领唱，音乐也仿照黑人歌曲的格调创作而成。奥德威是“奥德威艺人团”的领导人，曾写过不少艺人歌曲。李叔同在日本留学时，日本歌词作家犬童球溪采用《梦见家和母亲》的旋律填写了一首名为《旅愁》的歌词。而李叔同作的《送别》，则取调于犬童球溪的《旅愁》。《送别》不涉教化，意蕴悠长，音乐与文学的结合堪称完美。歌词以长短句结构写成，语言精练，感情真挚，意境深邃。歌曲为单三部曲式结构，每个乐段由两个乐句构成。第一、三乐段完全相同，音乐起伏平缓，描绘了长亭、古道、夕阳、笛声等晚景，衬托也寂静冷落的气氛。第二乐段第一乐句与前形成鲜明对比，情绪变成激动，似为深沉的感叹。第二乐句略有变化地再现了第一乐段的第二乐句，恰当地表现了告别友人的离愁情绪。这些相近甚至重复的乐句在歌曲中并未给人以繁琐、絮叨的印象，反而加强了作品的完整性和统一性，赋予它一种特别的美感。“长亭外，古道边，芳草碧连天。晚风拂柳笛声残，夕阳山外山……”淡淡的笛音吹出了离愁，幽美的歌词写出了别绪，听来让人百感交集。首尾呼应，诗人的感悟：看破红尘。
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