Winston Churchill has been portrayed hundreds of times in various films and television shows, yet he still remains, in the visual medium anyway, very much an enigma. Here's a man who was not trusted nor respected (he had a tendency to change political parties seemingly on a whim and then change back again), yet it is not overstating it that without him we would not have won World War II. To defeat someone like Hitler you needed somebody as single-minded and stubborn as he was. No one else in England's power elite, except Churchill, could have achieved that. Lord Halifax -- who was considered Neville Chamberlain's replacement when he stepped down -- was passed over in favour of Churchill to become PM. Based on Halifax's desire to offer further accommodations to Hitler, thank God that Churchill was chosen.
In over 100 film and TV shows, beginning in 1935 in something called Royal Cavalcade, Churchill has been portrayed by actors both famous (Rod Taylor, Richard Burton, Joss Ackland, Christian Slater (!), Bob Hoskins, Donald Pleasance, John Houseman, John Cleese (!), etc.), and not. Yet it wasn't until Albert Finney essayed him in the HBO docudrama The Gathering Storm (2002), and Brendan Gleeson in its sequel Into the Storm (2009) -- Hugh Whitmore wrote them both -- has anybody come close to giving us an intimate glimpse into the enigma who saved Europe.
Of the two, The Gathering Storm is the stronger. It tells the rather compact story of Churchill in the mid-1930s when he was out of favour and out of power. He was considered the lone voice in the wilderness for his dislike of what he saw coming. Ridiculed and practically exiled from government, he retreated to his family home to try to launch his return to power. Helped by his devoted, but exasperated wife, Clementine (played with layers of emotion by Vanessa Redgrave), Churchill rallies a small, very small group of loyal men and women around him to build a case that would show England what Hitler truly represented. Finney is fantastic as Churchill, getting at his simultaneous strengths and petty, almost childish, attitude towards colleagues and loved ones (one subplot that doesn't quite work here is that he fears that Clementine is falling in love with someone else -- Redgrave as Clementine has such regard for Finney's Churchill that we as the viewer are never convinced there was any real fractures in their marriage, even though in real life there supposedly were).
Into the Storm, on the other hand, tries to cover too much. Set during the war years from 1940 to 1945 and then during the time just after the war when he was driven from power, the film attempts to cram acres of story into the scant 96 minutes. Gleeson is in many ways the equal to Finney as Churchill. Since there's always been a bit of the 'big kid' about Gleeson (see him as Mad-Eye Moony in the Harry Potterfilms, or Ken in In Bruges), it is almost effortless for him to get at Churchill's childish side. Yet he also easily embraces Churchill's cast-iron resolve in the face of resistance at home, little help from the US (Len Cariou is very good as FDR) until after 1941, and, of course, the constant threat Hitler represented. Janet McTeer as Clementine here is a more cerebral actress than Redgrave, so the layers of emotion that Redgrave brought, are missing, but this is a Clementine who you believe would leave Churchill finally if he doesn't stop steamrolling everything and everybody in his life.
Taken together (ideally they should be watched back to back on one night -- both films are only 96 minutes each), this offers a truly compelling look at Churchill played by two different actors. But even these two films only lift the very corner of the veil that is Winston Churchill. Perhaps we will never really understand him in ways other than this: to defeat Hitler he had to think and in some ways become him. Nothing on offer in either of these two docudramas achieves that, but they are getting closer.