I Love You, Now Die: The Commonwealth Vs. Michelle Carter (2019)
Broken up into two parts -- the prosecution and the defense -- this documentary walks through the highly publicized trial of Michelle Carter, on trial for encouraging her long-distance boyfriend over text messages to kill himself in 2014. Carter was an easy villain: She represented everything that society hates and fears about teenage girls, a "manipulative" and "crazy" petite, blonde white girl with cartoonishly expressive drawn-on eyebrows. While I Love You, Now Die acknowledges as much, it also upends the assumptions a casual follower of the case might have harbored. Carter had met her boyfriend, Conrad Roy, only a handful of times over their two-year relationship that existed primary over text messages and Gchats; Roy was incredibly depressed, and Carter, prescribed SSRIs herself, was a horribly lonely person convinced she was helping Roy by badgering him to take his own life. The binary presentation leaves a few gaps that could have been plugged up, but at its core, I Love You, Now Die is a thoroughly modern and messy story about teenagers, technology, mental health, and our justice system that's ill-prepared to juggle it all.