Diamonds and Pearls (1991)
There’s a handful of placings on these pages that I feel compelled to justify as their ranking swims against the tide of popular opinion. Money Don’t Matter 2 Night is one such song and didn’t even feature in an early version of this list which may appal all those with it in their top 10. It certainly caused an outcry from a friend of mine who’s only familiar with the singles and partly due to their reaction it’s barged its way back in, ousting out the Stop The Cavalry bugles of Man in a Uniform. It’s not that I don’t think the music isn’t great – it is – it’s just that hearing someone with money sing about the unimportance of it all seems a little unseemly. The three verses are pitched to a gambler, an investor and the US Government in the midst of the Gulf War, but the tone, like the later Rich Friends or even the earlier Pop Life chimes as off-key, not helped by an accompanying Spike Lee video that pounds the poverty angle low and hard. But like Prince himself once said: “musical excellence, like beauty, is in the eye of the beholder” and when held in the right light Money Don’t Matter 2 Night is a joy to behold. A smooth pop back-rub, with enough vocal and chord idiosyncrasies to work its fingers in deep. If I was only limited to just one Prince song a day then I couldn’t go a complete calendar year without hearing it, so it creeps back into the list at #365 to be listened to on New Years’ Eve. And if that offends your sensibilities, wait to you hear where its oft-despised, album-mate Jughead ranks (trigger warning: higher).

I agree with your easily offended friend. Should be in the top 150 at least. If there is a hell, and i am not sure there is, Jughead may be playing on a loop there with Life of the Party, Strays of the World, and most of the Rave album.
Nah surely it’d be a ‘Purple and Gold’, ‘Graffiti Bridge’, ‘All the Midnights in the World’ mega-mix on eternal loop.
Actually no – my daughter loved purple and gold (albeit at the unrefined age of 3) – and so it will always have a fondness in my heart.
Hey, “Graffiti Bridge” is a perfectly okay piece of cheesy fluff. Certainly not the worst thing ever. Try listening to it on Christmas Eve, watching snowflakes and taking a break from listening to other Christmas so-called “classics” on the radio, and it will suddenly sound pretty okay.