Sometimes I'm serious.
As a documentary filmmaker Michael Moore is possibly the most famous, successful, and wealthiest of all-time. In both US and international grosses, he directed the all-time record money making movie with Fahrenheit 911. He has more entries in the top 50 highest grossing films than anyone else. The only documentary filmmaker who might be more well known than Moore is Leni Riefenstahl, and she made propaganda flicks for Hitler to be in the running. Moore was divorced a few years ago, but he was worth 50 million dollars before divorce. Moore gets to make films on serious issues, spends more time on camera than anyone else in his movies, and gets to interject as much comedy into his movies as he wants. He'd be wise to stick with making documentaries over his acting career.
Is he a fraud playing a character or is he totally himself in the movies? I don't know for sure. I'd guess it's mostly an exaggerated version of himself on camera most of the time. I'm guessing he supports the Democratic party, would rather not have common people crushed like bugs by corrupt authorities, and would rather support sane policies like letting gay people live instead of being burned at the stake. He is probably motivated by personal interest just like most are. Moore presents biased information in favor of his beliefs often. He grandstands in a pompous way at times. He lives well in nice homes and eats like a king despite looking like a slob.
Moore almost always writes, directs, and appears as the lead journalistic documentary character/himself in all of his movies. He has dabbled in acting, but never made much effort outside of his own projects.
I have seen every movie of his and his TV series TV Nation and The Awful Truth. My reviews of his directing work:
Roger and Me- Put him on the map. An expose of him trying to meet the CEO of GM. A personal touch since many of his friends and family were negatively impacted by GM closing in his "hometown" of Flint, Michigan. A bit funny at times. A bit dry at times. A bit dated now? Maybe. But this one sets the tone for all of his later work- it makes obvious points though targeted confrontations, sarcasm, and one sided facts.
Pets or Meat- A bit more gruesome extension of the negative effects of GM in Flint, Michigan. Just a short film.
Canadian Bacon- Moore's most active attempt in a feature film, non-documentary style. The notion of a fake war between USA and Canada is a good idea, but not executed as well as maybe it should have been. Not a great movie, but has some good parts. One of the last movies for John Candy. Rip Torn is enjoyable in the movie too.
TV Nation and The Awful Truth- Similar themes with his TV shows and movies: Moore goes after big government and corporate fat cats that systematically harm the working class and minorities of America. The Awful Truth came later, probably had a bigger budget, and was probably slightly better.
The Big One- Probably the most forgettable Moore movie in my opinion. Not bad, but doesn't stand out in any way among his other movies. He comes hard at Nike, but this seems like a relatively easy target.
Bowling for Columbine- At least in the running for his best movie. Probably his funniest movie and definitely the funniest one at the time he made it. Had funny cartoons, fantastic use of music, and drove home obnoxious points about the NRA and gun control. Best moment: An interview segment with Marilyn Mason- who was being blamed by many in the media and the country as a whole for the Columbine incident. Manson spoke eloquently and brought up several intelligent points about why that was absurd. The worst moment was when Moore confronted Charlton Heston. I'm almost positive Moore lied to get the interview and seemed to take advantage of an old guy. To be fair, that old guy was the head of the NRA and said some fake brash things in public to defend guns.
Fahrenheit 911- Probably the biggest movie Moore made, about the subject that defined the biggest news event of that time most directly. Funny and challenging, even if quite one sided at times. I think it will be what he's most remembered for. If you only get to pick one to watch from Moore, this should probably be the one.
Sicko- Even though this had good moments, it was mostly disappointing. Moore's most boring film. Health care often is less than a glamorous issue. The most noteworthy moment of the film was when he controversially (illegally?) went to Cuba to see how their health care actually was.
Slacker Uprising- A movie mostly about getting young people to vote, and vote for the Democratic party. Had funny moments, but not as good as his best.
Capitalism: A Love Story- Not as much humor injected into this one, but it consistently brought up interesting info about finances. Preachy, but his "facts" made more sense than in some of his other films.
Where to Invade Next- Enjoyable and funny. It had some excellent points and mostly praised specific foreign policies that work well on location in those lands. The film points out that these ideas are not new, but are based on ideas and principles that were originally created in the USA.