I divide songs to three main categories: there are "easy", "challenging" and "too difficult" songs. Hence "a challenging song" means that I'm able learn it but I have to work on it.
The song may be challenging because of the range it requires (high notes and/or low notes) or because of its tessitura.
The language may be a challenge (Russian, Finnish...)
Then there are unusual rhythm patterns (syncopes are always a big challenge for me), interpretation-related issues, tonality, intervals...
In order to determine how challenging a song is you have to analyze the song and compare the results with your present skills. If you have all the notes, know the language, love the melody, understand the lyrics and keep on humming the melody all the day the learning process is probably very easy.
Still, learning "easy" songs becomes quickly boring. Nothing feels better than "conquering" a challenging song. (My latest "challenge" has been "Una voce poco fa" because of the coloratura and low and high notes. I never thought I could really do that!)
Enjoyable challenges!
-Marika
>I was thinking...what would be considered "challenging" in a song to sing? >What MAKES it challenging? Also....does it have to do with pitches, the >music, or the over-all song?
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