Moonbeam said:

Sorry, but that's not possible.

Bracket #3:
Soft and Wet
v.
She's Always In My Hair

D.M.S.R.
v.
Bob George

Uptown
v.
Wasted Kisses

Head
v.
Bambi

When You Were Mine
v.
Dolphin

Electric Chair
v.
Automatic

Dirty Mind
v.
Cream

The One U Wanna C
v.
Girls and Boys

Bracket #4:
The Beautiful Ones
v.
I'm Yours

My Name is Prince
v.
Letitgo

The One
v.
Let's Work

Cindy C.
v.
The Dance

Old Friends 4 Sale
v.
I Wish U Heaven

Paisley Park
v.
When Doves Cry

1+1+1=3
v.
Raspberry Beret

Anna Stesia
v.
Diamonds and Pearls

In the interest of expediting the process, here are Brackets 3 and 4 together. Two days of voting on these two, and then we'll be ready for the second round.

Bracket #3:
She's Always In My Hair--Soft and Wet was really a really nice R&B jam for its time, but all in all, a little formulaic. She's Always In My Hair, on the other hand, just plugged in the guitar and rocked it.

D.M.S.R.--Was jamming out to this one on the way home last night, in fact.

Uptown--Wasted Kisses was pretty underwhelming for a hidden track that I had to wait umpteen minutes for.

Head--Having Lisa sing...er, well, speak, I guess, on that song was genius. This wasn't as tough as I thought it would be when I first looked at the matchup.

When You Were Mine--Dolphin weighs in well in the "anthem" category, but When You Were Mine is just one of his most fun songs...even though the subject matter's a little depressing when you really digest the lyrics.

Automatic--I kinda only recently really embraced Automatic, and now it's become one of my favorite jams off of any album, let alone 1999.

Dirty Mind--This one kinda split the difference between New Wave, funk, and punk. Really should get even more props than it does. Cream is a great song, and it'll be remembered for being successful, but is it an event? Dirty Mind was an event.

Girls and Boys--The One U Wanna C is a great, fun song, but so is Girls and Boys, and it has a richer sonic palette with the horns. Probably my closest matchup in this bracket.


Bracket #4:
The Beautiful Ones--Yeah, a lot of you were perfectly right. This one's not close, even though I'm Yours was like a kick in the head at the end of a pretty formula R&B album like For You.

My Name is Prince--As I've said, it was the first song that really kicked open the doors to Prince's music for me. I'm very sad, though, that Letitgo ended up drawing this matchup, because I think it could have done well here.

Let's Work--Dirty funk wins again over smoothed-out ballad...

The Dance--...but smoothed-out ballad gets one back here.

I Wish U Heaven--Just gorgeous.

Paisley Park--When Doves Cry deserves every bit of praise it gets, but Paisley Park deserves a lot more than it gets.

Raspberry Beret--All-time Top 5.

Anna Stesia--Diamonds and Pearls, for me, is the definition of overplayed. Like it a lot, but got tired of hearing it.