I cannot pick a favorite. For one thing, it has been ages since I listened to anything all the way through. But also, each one I like has some things about it that glares with flaws. It's almost like each of them exists in their own 'timespace' for me. And yes, I want to slap the **** out of myself for that sentence, so I will save you all the trouble. SLAP !
I know that SA and OSOTM are last and next to last. But BD, WH, RAL, and TISL are all a bit neck and neck, depending on the day and what I want. BD has the best consistency in quality of songs. But I find L&L and Highwayman to be almost unlistenable. And the sameness of the production almost feels flat to me now. It took years for me to comprehend the criticism upon it's release about the "LA creme de la creme studio musician" sound it was slagged for. But now I hear it. Her voice is great on the title track and Edge is epic, vocally.
WH is a lot of fun to listen to. But it suffers from production too in parts. The keyboards sound super cheesy and dated. On the other hand, the only song I absolutely cannot stomach is 'Gate and Garden', with IAF as a runner up. The rest I still enjoy. Of course, WH is the big epic here - a true crowning achievement in her career even with the audible strain in her voice. There are other great moments too.
RAL is a brilliant mess. Parts of it are downright embarrassing to listen to, but I like them anyway. It lacks the cohesion of BD and WH, but the things I love about it: ICW, NSW, SBS, and others, are so much fun. Even The Nightmare, which I consider to be her quintessential "post it" song, is an oddly entertaining diversion. This is the only record I don't feel compelled to skip songs on, strangely enough. Although I far prefer the outtake of RAL to the one on the record, and HAEWAFY is a larger and more powerful animal now than it was on that record.
TISL was my favorite for a looong time. But, with time, I find that I always skip Everyday (HATE IT, so beneath her, worse than SIAB and barely above LAHGT), TMMS, LC, and Love Is. That's a lot to skip. But I shiver in wonder at TISL. I love that track. It is brilliant. As good as anything she ever did. I also still gape at the falsetto in Sorcerer, and think JS did a bang up job with FFG and Planets. I am in the minority loving TFFT and IOL - but I love both of those songs. As far as IOL goes, she is just not capable of writing such a straightforward, simple song with a beautiful melody like that anymore, and it was a great gift, as far as I am concerned, from Sheryl. TFFT is just hella fun to sing.
TISL has great highs, and wretched lows.
I guess, after writing this, it might be RAL by the tail end of a ribbon on a tambourine. A tambourine, it must be noted, that is stained with brandy, dusted with coke she sneezed out, and headed straight for Betty Ford. Ah, the beauty of a supernova collapsing on itself.