I used to follow Britney so closely in 2007 as a teenager, sort of like watching a car accident. I felt awful for her but couldn't tear myself away. In hindsight I was definitely a huge part of the problem and helped fund the horrible tabloids and paparazzi. Anyway, I was so relieved of course when it seemed like Britney was out of the woods and "saved" by her family (this was before people realized how cruel the conservatorship was), but I felt like I had to fill some sort of hole with worrying about a celebrity, and LiLo's drama definitely filled it.
It's so funny now looking back that I used to conflate LiLo's relationship with Sam Ronson and her not being straight with how "bad" she was or with her drug use. I used to think that if I could just be friends with Lindsay I could save her from all the bad influences including her gayness. Now of course I realize I'm queer myself and that I actually just had a huge crush on Lindsay.
I also wonder sometimes about her career... It's basically completely dead, I cannot imaging Lindsay ever making a significant impact acting again. But at the time, people saw her fall the same as Britney's, she was considered such a promising actress, destined to win many Oscars; she really was the equivalent of Britney in the acting space. If Lou et al had succeeded in putting her under a conservatorship, do y'all think she would have made a comeback in her acting career the way Britney did on the Circus and FF tours? And if so, looking at Britney, at what cost. Would Britney be happier now fading into relative obscurity like LiLo? LiLo did always seem to thrive off of attention more than Britney...
Anyway, just some disjointed thoughts.