Best political documentary

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Primary is a 1960 Direct Cinema documentary film about the 1960 Wisconsin primary election between John F. Kennedy and Hubert Humphrey for the United States Democratic Party nomination for President of the United States.

Produced by Robert Drew, shot by Richard Leacock and Albert Maysles, and edited by D. A. Pennebaker, the film was a breakthrough in documentary film style. Most importantly, through the use of mobile cameras and lighter sound equipment, the filmmakers were able to follow the candidates as they wound their way through cheering crowds, cram with them into crowded hotel rooms, and to hover around their faces as they awaited polling results. This resulted in a greater intimacy than was possible with the older, more classical techniques of documentary filmmaking; and it established what has since become the standard style of video reporting.

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Recount

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Point of Order! is a 1964 documentary film by Emile de Antonio, about the Senate Army–McCarthy hearings of 1954.

The Army–McCarthy hearings came about when the Army accused Senator Joseph McCarthy of improperly pressuring the Army for special privileges for Private G. David Schine, formerly of McCarthy's investigative staff. McCarthy counter-charged that the Army was holding Schine hostage to keep him from searching for Communists in the Army. The hearings were broadcast live on television in their entirety and also recorded via kinescope. This film was created from those kinescope recordings.

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Point of Order

I don't know where it stacks up but there's a great documentary about Anthony Weiner that came out within the past few months. I haven't seen it but I've heard very good things. I heard an interview with the film makers and they had access to things they were embarrassed to.

It's called Weiner:

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The 41st President of the United States, George H. W. Bush reflects on the highs and lows of his life, sharing personal anecdotes from his childhood, his family, serving in WWII, his political career, and more.

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Dinosaur 13.

probably not the best, but one of the best recent ones is Best of Enemies

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Best of Enemies is a 2015 American documentary film co-directed by Robert Gordon and Morgan Neville about the 1968 televised debates between intellectuals Gore Vidal and William F. Buckley, Jr., and their aftermath

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Though only a little bit about politics Journeys with George was an interesting look in how politics are covered by the media.

Granted what was on display most of all in the movie was how petty and ill tempered the press tends to be.

Feed (1992)

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nytimes.com
JANET MASLIN
Published: October 7, 1992

"Feed," a compendium of candid glimpses at this year's Presidential candidates, is as cruel a film as you may ever see. The contenders are caught unawares, some during seemingly private moments just before their televised satellite feeds are scheduled to begin. This is the time for throat-clearing, for smile-practicing, for working on the handclasps or upbeat gazes or other reassuring touches that make up a public demeanor. "Feed" observes these studied politicians both before and after they become their familiar selves.

The result is a revealing look at these specific candidates and the political process itself, at least as it manifests itself on television. This film, like C-Span's "Road to the White House" series, presents the Andy Warhol version of campaign posturing. Some minor but fascinating aspect of a candidate's nature is inevitably exposed when that candidate is shown glad-handing strangers or struggling to understand the quirks of high-tech equipment that doesn't work (Senator Bob Kerrey trying to answer questions posed by an interviewer he cannot hear). Jerry Brown, viewers of "Feed" learn, is a guy who can pick a fight over whether his necktie looks straight.

This film's spy tactics are at their most merciless in using the warm-up material that precedes live broadcasts. President Bush is seen sitting looking vacant for a very long time; Gov. Bill Clinton coughs badly and curses himself for getting teary-eyed; Ross Perot tells what he thinks is a corker of a racy story. Anyone, it might be argued, could be made to look foolish in such a context, and the glimpses seen here appear deliberately unkind. They are riveting in spite of that, and so are the film's campaign sequences, which are fairer since most of them take place in public. One quality worth studying is how a candidate responds to endless petty ambushes along the campaign trail.

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Ken Burn's The Roosevelts (TR and FDR) on Amazon
Inside Job
Ken Burn's Prohibition