Lindsay Lohan - General Discussion

I think also, something to take into consideration is that Lindsay is extremely close to Cody and Ali since she basically helped raise them. Even when she was out here getting into all sorts of trouble she was still having to be kind of a parental figure for them. And lord knows what growing up in that household was like. So maybe Ali really does want to do the whole music and Lindsay is supporting her because that's what she does.

Maybe Ali felt some type of way about Lindsay going to Cascablanca / Universal too get her a deal only to be told "um not thanks but btw you still owe us an album and we want that" then Lindsay started getting acting gigs again so I guess it worked out.

I do still want the album tho. She has one of my favourite voices and her material is extremely strong.
I think her voice was good, not great technically, but emotive and a perfect fit for the music she was making at the time. But that sound is over now, and I don't trust that any studio hookup would recreate that magic for her. She's doing acting because she's good at it and it's way more lucrative. There's basically no risk compared to being in music. Other than a few thousand nostalgic gays and girlies she doesn't have the fanbase to make it worth it.
… But hadn’t Lindsay already released the song by the time My December was out? That would have been asking for unwanted press comparisons.
I don't blame Kelly at all for passing on that song, My December was pretty clearly a very personal album for her (probably her most fully personal/thought out ~body of work~ alongside a couple of others) and it all came from a specific time of her life. Adding a Lindsay Lohan cover would have been super out of place as far as the intention behind the album goes, and it would have watered down the vision for what the album was. On an album like All I Ever Wanted, sure, but My December was meant to be what it was (although it could have had better mixing, but I digress).
I honestly don't think Lindsay is (or should still be) thinking about a pop career anymore at this point in her life (and it's not just because of Aliana), it made sense in 2019/2020 to give it another go but (pandemic messing up their plans or not enough interest aside) clearly more people care about her movies and that's where the money and potential future career highs might be for her so that should be her priority. She can always sing a song or two for a soundtrack (like the Freaky Friday sequel will be a great opportunity for that), maybe collaborations with other people if that comes about, with the possibility of a musical happening as well as she mentioned so the music stans still get something. I mean I know it's just a Christmas song but her Jingle Bell Rock cover hasn't even hit a million streams on either Spotify or Youtube yet, she didn't tour back when she was at her peak either so besides doing it for fun I can't imagine they'd be seeing a lot of ROI. Maybe down the line if she's really passionate about it I can see her releasing a covers album or a compilation with the inclusion of unreleased and/or new original stuff but that's about it now.
Flop? It was a top 20 hit and a top 10 airplay hit. Y’all keep rewriting the success of that song!
Flop might be harsh, but it was barely Top 20 and I recall it falling like a rock after its peak. It also really struggled internationally, which was unfortunate after “Suck” got her back on track.
I remember when I was 15 (I'm 31 now!!) and being so buzzing for Spirit in the Dark.

I always remember her mum on "Living Lohan" on E! saying the album was coming soon etc.

When we got Bossy, I got even more excited. To think, I'm 31 now and still no sign of it ever happening.