By the way, I am treating the Sixties as taking place from 1961 to 1970. In the Gregorian calendar there was no year 0. This is why The Apartment (1960), which is my second favourite film of all time, does not appear on this list (it appeared in last year's National Classic Movie Day post, for the Fifties). While no movies from 1970 made this list, it is fully possible that they could have by my reckoning (Catch-22 numbers among my favourites).
Anyway, without further ado, here are my six favourite films from the Sixties. For simplicity's sake, I am listing them by year of release.
To Kill a Mockingbird (1962): To Kill a Mockingbird was the first film I saw in a theatre that would later be considered a classic. In 1973, when I was 10 years old and in third grade, we took a tour of the 4th Street Cinema, which included getting to watch a movie. At 10 years old there were parts of the plot I didn't yet understand, so I didn't quite appreciate the movie at that age. Fortunately, I would see To Kill a Mockingbird again when I was a teen and I would realise just how truly great the movie is. It has numbered among my favourite movies ever since.
Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964): I have to confess that ever since I was a kid I have had a somewhat twisted sense of humour. Of course, the Sixties produced a number of comedies that would naturally appeal to someone with a sense of humour like mine. Possibly the best black comedy the decade ever produced was Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (hereafter simply Dr. Strnagelove for brevity's sake). Let's face it, one cannot get much darker or much more twisted than a comedy based around nuclear annihilation! The laughs come non-stop in Dr. Strangelove, with bravura performances from the entire cast.
The Great Escape (1963): When I think of the Sixties, I often think of the many epic World War II movies released during the decade. Possibly the best of the World War II epics of the Sixties is The Great Escape. Loosely based on the real life escape from German POW camp Stalag Luft III in 1944, The Great Escape details an escape from a POW camp. The Great Escape features an all-star cast including Richard Attenborough, Charles Bronson, James Coburn, James Garner, Steve McQueen, Donald Pleasence, and yet others. What is more, each and every member of the cast gives a great performance. The Great Escape is not merely an action film, but a tale of heroism with a good deal of depth to it.
A Hard Day's Night (1964): I have been a fan of The Beatles since childhood. In fact, not only cannot I remember the first time I ever heard The Beatles, but I cannot remember the first time I saw A Hard Day's Night. I am guessing it was probably when it first aired on NBC Tuesday Night at the Movies in 1967, although I cannot be certain (I would have only been four at the time). Regardless, there has never been a time that I have not loved this movie and it has always numbered among my absolute favourites. I have seen it numerous times and hosted numerous TCMParties for it on Twitter. As part of Turner Classic Movies' Fan Favourites series, I even introduced it with Ben Mankiewicz in April 2015.
The Loved One (1965): As I mentioned earlier, I have always had a twisted sense of humour, and one cannot get more twisted than The Loved One. Loosely based on Evelyn Waugh's 1948 satirical novel of the same name, the tag line for The Loved One was "the motion picture with something to offend everyone!" And that is just about true. The Loved One lampoons the American funeral industry (much as Evelyn Waugh's original novel did), Hollywood (much as Evelyn Waugh's original novel did), religion, Oedipal complexes, overeating, the rich, the military, the space programme, television, and yet more. Along with Dr. Strangelove and The President's Analyst (1967), it is among the most outrageous comedies of the Sixties.
To Sir, with Love (1967): I have a confession to make. I absolutely hated school. I simply did not like having to stay in a room all day, often studying some subjects in which I had little interest (to this day I am not a big fan of mathematics). Strangely enough, the "inspirational teacher" genre is one of my favourite genres. Perhaps the first movie I ever saw in the genre was To Sir, with Love and, except for Stand and Deliver (1988), it is still my favourite. To Sir, with Love works on multiple levels. At its most basic level it is about a teacher trying to get students in a school in the East End of London to improve themselves. On another level it is about a black teacher facing such obstacles as racism in mid-Sixties London. On yet another level it is about the students, most of who live in poverty, and the obstacles they face. This makes To Sir, with Love among the most complex of the "inspirational teacher" movies.
The President's Analyst (1967): Like Dr. Strangelove and The Loved One, The President's Analyst is another one of the Sixties' outrageous comedies. Released at the tail end of the Sixties spy craze, on the surface The President's Analyst is yet another spy spoof. What sets it apart from the many spy spoofs of the era is that it is also a social and political satire that sends up everything from the United States government to middle class suburbanites to, well, the phone company. In fact, the only people that seem to be treated sympathetically in the movie are either spies or hippies! The President's Analyst certainly deserves to be better known than it is.