The most poignant song for me is probably "Sometimes It Snows in April" but that's pretty self-explanatory if you listen to it (the last song in the acoustic guitar clip I posted). Prince constantly sung about becoming a better person, life/death, and getting to heaven so perhaps it's fitting he passed away in April.
In terms of lyrical depth, his songs were full of multiple layers of meaning in terms of politics, religion, humanity, love, sex, etc. You just have to pay attention.
Let's Go Crazy is not about having fun, going partying, letting people get you down and off the dance floor etc. It's a song about fighting for more than just every day pleasures because your soul is immortal and there is heaven and hell. The "de-elevator" bringing people down is actually "the devil" and he encourages you to "punch a higher floor" if your soul is being dragged downward immorally. His 1980s manager Alan Leeds (who also managed James Brown) mentioned the tragic absurdity that Prince passed away in his own elevator.
I didn't agree with his religion but Prince's lyrics are full of double meanings and layers and layers of depth. It's actually all very apocalyptic. "Party like it's 1999" is not just a song about partying and fun. Read the lyrics. It means party like it's the end of the world. It's a song about nuclear war and the year is significant because it's a post-millennialist/cold-war theology in terms of people believing the end times would come with the millennium.
It perfectly demonstrates the dichotomy between the hedonistic/party lifestyle he seemed to advocate and embody on the outside, and his inner conflict with his moral soul. That followed him his whole life.
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