Yhlee wanted to know my favourite German song. Well, I had to divide the answer(s) by genre, and even then I had a hard time narrowing them down. However, here are the results:
Song that started out as a composed Lied based on a poem and then became a folk song with a lot of people not knowing its origin anymore:
a) Das Wandern ist das Müllers Lust
Melody by Schubert, here sung by Jonas Kaufmann. The APs and I still sing this occasionally when we are hiking. (Well, Dad and I do, my mother says we are embarassing.) As cheerful songs go, this is indeed just asking to be sung when in a good mood and taking in beautiful scenery. No matter how little I'm able to carry a tune.
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b) Ich weiß nicht, was soll es bedeuten/ The Loreley Song
Melody by Friedrich Sibert, original poem by Heinrich Heine. Like many of Heine's poems, this was quickly set to music and Sibert's version was only one of many, but it's the one which stuck. It became one of the most popular folk songs and was very appealing especially to my teenage self for its moodiness. A sad and infamous part of the song's story is that when the Nazis came to power, this song was so popular that they couldn't eradicate it from the national consciousness, but what they did was print it with "Text: Unknown poet" from this point onwards in every collection of popular German songs. This was kept up well into the 50s and 60s. Thankfully, when I just checked YouTube for versions I saw that Heinrich Heine was credited in every single one of them. Have one presented by Pam Kappis and Paul Bratfisch.
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Because the song had become so incredibly popular in the 19th century, there were any number of parodies in the 20th (including one by Kästner), and because it's that well known, you can even do parodies in children's tv and bet on the kids knowing what is being parodied. Like here:
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Songs from operas and operettas
Two very different ones. For sheer romance, there's Dein ist mein ganzes Herz, here sung by Jonas Kaufmann again. From the operetta Das Land des Lächelns by Franz Lehar. Which was in fact the first operetta I ever saw and heard, and I fell in love with the song.
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And then there's the ultimate female revenge song, Seeräuber Jenny, from the Three Penny Opera, composed by Kurt Weill, lyrics by Bert Brecht (and friends). Here sung by the very first Jenny, Lotte Lenya:
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Pop and Rock Songs
Unsurprisingly, these are songs from the 1980s, because that's when yours truly was a teenager. First, there's Sonderzug nach Pankow by Udo Lindenberg, here presented in 1983. Erich Honecker, who's adressed and made fun of in the song was the head of the GDR at the time. I grew up not that far away from the border.
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Then I moved to Munich to go to the university, and there's no band like the Spider Murphy Gang when comes to capturing Munich in the 1980s. For two very different aspects, between I can't decide, have first "Schikaria", which makes fun of the Yuppies in general and the Schwabing crowd in particular:
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And then there's Sommer in der Stadt. Still applicable. Let me add that Spider Murphy Gang sings in Bavarian dialect, so if you know a bit German and are still not understanding a single word, that's why.
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Modern folk song
Just once choice in this category. Über den Wolken by Reinhard Mey. No other song has managed to capture that well what it means that we earthbound creatures are able to fly. BTW, if I have to narrow down my selection of songs to just one because there's a gun at my head, this would be it.
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Songs for children
The various series I watched as a child came with songs, as did, btw, the dubbed Disney movies. (And they employed the best available, for example Reinhard Mey for the German version of Robin Hood. Also, I like the German version of Bare Necessities from The Jungle Book - Probier's mal mit Gemütlilchkeit - better than the English original.) But the question was for German songs, and for sheer nostalgia and adorable silliness, there's none like the Lummerland song from Jim Knopf und Lukas der Lokomotivführer:
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The other days