Create a musically diverse and musically interesting Prince playlist

My father-in-law is a musically-literate classical music buff whose popular music knowledge is mainly in the area of '60s/'70s singer-songwriter types. His curiosity has been piqued regarding Prince, however; I’ve been a fan for 30+ years, but I feel ill-equipped to construct a playlist to impress him, given his background.

So, what are some suggestions?

From Billboard Top 100 (may not be accurate) The asterisk is for songs I like…

1980
95. I Wanna Be Your Lover

1983
41. 1999 *

1984

  1. When Doves Cry
  2. Let’s Go Crazy
  3. Little Red Corvette

1985
51. Raspberry Beret *

1986
19. Kiss *

1987
38. U Got The Look
60. Sign ‘O’ The Times

1989
44. Batdance

1990
98. Thieves In The Temple

1991
66. Cream *

1992
25. Diamonds and Pearls *

1993
52. 7

1994
19. The Most Beautiful Girl In The World *

I bought the Diamonds and Pearls album when it came out…

It has a lot of variety - some of the songs were funny… then there’s this:
Gett Off - more sexual than “Cream”

Insatiable - sexual and intimate

Thanks. I’ve got a heap of his albums (about 12, not including compilations), but I need to really ponder the breadth of his music. Around the World in a Day is also quite varied.

I’d add “Lady Cab Driver” – a funky number from 1982’s 1999 – plus maybe “Housequake” from Sign o’ the Times and/or “Raspberry Beret” (1985).

ETA: I see Raspberry Beret was already mentioned.

Also add “Bambi” from Prince (1979) to showcase some of Prince’s rock guitar shredding.

How about "Erotic City"? - YouTube

Thanks, everyone. These are all great suggestions.

I’d have to include some tracks off Dirty Mind. It’s hard to figure out which–they’re all so good and different–but I’d go with “When You Were Mine” for it’s melodic, earwormy New Wave goodness and, perhaps somewhat under-rated, the bouncy “Do It All Night” for its infectious groove and bassline. For me, those are the two catchiest songs on that album. If you want to hear punk/post-punk as interpreted by Prince, you might want to try the raunchy ode to incest, “Sister.” I’m not entirely sure I’m a big fan of that song, but it shows his stylistic diversity. The title track also is a nice New Wave number that calls to mind something more like the B-52s than the R&B/funk type of music many people associate with Prince.

I would start with The Hits/The B-Sides: http://www.amazon.com/dp/B000002MNF/?tag=googhydr-20&hvadid=106024196844&hvpos=1t1&hvexid=&hvnetw=g&hvrand=17364165502182155086&hvpone=16.49&hvptwo=&hvqmt=b&hvdev=t&ref=pd_sl_3mzex9i4md_b

Add Sign o’ The Times

And the song, She Spoke to Me: https://www.amazon.com/gp/product/B002C7C29Q?ie=UTF8&keywords=prince%20she%20spoke%20to%20me&qid=1461930540&ref_=sr_1_fkmr0_1&s=music&sr=8-1-fkmr0

Start with How Come You Don’t Call Me Anymore (B-sides), When You were Mine, a hit like 1999 or Little Red Corvette, then Raspberry Beret, then The Cross off Sign and end on She Spoke to Me for Brazilian pop and Coltrane jazz.

6 songs with great coverage.

Solid options so far. I would say you need to include Strollin and probably The Truth to add to the diversity of style.

Edit; also soft and wet for chronological range

These are good suggestions but any serious understanding needs to be rooted in their legacy. Throwing a few songs will not provide the rich understanding of this mans’ accomplishments and what he meant.
Just as i attacked the music that came before me by listening to the core albums that is how it should be done or they’ll be left wanting…so
Dirty Mind
Controversy
1999
Purple Rain
ATWIAD
Parade
Lovesexy
B-Sides on the Hits release
SOTT (though it badly needs a remaster…sounds like garbage)
Lovesexy
SOTT LIVE- very important
Madhouse
The Time all 3 albums
Then you can start to branch out to the later stuff
Gold, Symbol, Rainbow children, lotus flower, Musicology, 3121-

I doubt that the OP’s dad is going to start by listening to 15+ complete albums. You gotta get him to want to do that.