Michael Moore is a filmmaker I associate with high school, the same way members of the previous generation like to namedrop John Hughes and then never shut up about him. The major events of my teenage years were the Columbine shooting in 1999, and the September 11 attacks in 2001, and wow, that's depressing. The films Moore made in response to those events—2002's Bowling for Columbine, and 2004's Fahrenheit 9/11—were, at the time, huge deals. Not just for ticket sales or award nominations, but in terms of what people actually talked about in those pre-social media caveman times. I wasn't even a huge fan of Moore's confrontational edutainment shtick, but he dominated the conversation in a way that few documentarians have before or since. It's worth remembering that Fahrenheit is still the highest-grossing theatrical documentary, and Columbine is in the top 15.
That said, I haven't paid much attention to Moore in the last decade, despite his pretty steady output of issue-driven work. His latest, Where to Invade Next, walks a sometimes awkward line between his articulate political convictions and his distracting antics, but he's still working with the solid toolkit that served him so well in the early aughts. Structurally, Invade isn't as laser-focused as something like Columbine or Fahrenheit, which is both a blessing and a curse.