It occurred to me recently that in my survey of philosophical music I had too long overlooked perhaps the premiere philosopher of transcendent pop music, Mr. Stevland Wonder (an artist I had the exquisite pleasure of hearing perform live in 2016).
Perhaps the most unique aspect of Stevie Wonder is the way he combines great spiritual, emotional and intellectual depth with funky-yet-tuneful harmonies. So many artists are either deep/challenging OR listenable/danceable so getting both in one package is no slight feat.
His catalog of philosophical songs is long, but here are a few to get you started:
Stevie on GOD/Religion
Stevie on Ignorant Beliefs
Stevie on Social Inequities
Stevie on Race and the Oneness of Humanity
Stevie on Love
Stevie on Reincarnation/Oneness with the Universe
Stevie on Politics and Hypocritical Politicians (Nixon)