He thought about how he could put such complicated lyrics(contents) into a pop song.
He thought carefully about how to include such complicated lyrics (contents) in a pop song.
「複雑な内容の曲をいかにポップに歌うか考えた」= He thought about how he could put such complicated lyrics(contents) into a pop song. / He thought carefully about how to include such complicated lyrics (contents) in a pop song.
ボキャブラリー
thought about = 考えた
how = いかに
put = 入れる、含める
such = そんな
complicated = 複雑
contents/lyrics = 内容
pop song = ポップの歌
carefully = 慎重に