After years of only considering expensive superproductions to be the best film of the year, the Academy broke all the rules in 1960, ignoring impressive epics like Spartacus and Exodus for Best Picture and selecting a black and white comedy that performed only moderately at the box office. But for once the Best Picture really was the best picture, as Billy Wilder's melancholy tale of a nebbish junior executive lending out his bachelor apartment to his bosses for their extramarital escapades and finding love in the process is as entertaining and touching today as when it first premiered. The Academy's selections weren't universally discriminating in 1960 - their preferences for the mediocre work of Elizabeth Taylor in Butterfield 8 and Shirley Jones in Elmer Gantry for acting awards have been continually derided in the decades since, and they overlooked classics like Psycho, Spartacus, and Inherit the Wind for a Best Picture nomination in favor of John Wane's interminably self indulgent The Alamo - but naming The Apartment as Best Picture just might indicate that Oscar has a heart beating behind his golden chest. It features superb work by Jack Lemmon, Shirley MacLaine, and the under-appreciated Fred MacMurray (who gave unfogettable performances as villains for Wilder in this and Double Indemnity while spending the rest of his lucrative career playing bland nice guys for everyone else), and Wilder became the first person to take home three Oscar statuettes for the same film for his screenplay (with I.A.L. Diamond), production, and direction.

West Side Story did not do well at the 1957 Tony Awards, winning only one trophy for Jerome Robbins' landmark choreography (the big winner that year was The Music Man). The film did rather better, winning a near-record 10 Academy Awards including being the first of four musicals in the 1960s to be named Best Picture. West Side Story is far from perfect - the Jets are a rather timid bunch reminiscent of the Bowery Boys, whose idea of violence runs along the lines of throwing rocks and cans at their opponents (they wouldn't last five minutes in the world of Boyz N the Hood), and Richard Beymer's performance as Tony is as stiff as plywood. But the dancing is miraculous (despite the fact that Robbins was fired from the film with less than half the shooting done because of his costly perfectionism) and most of the performances are superb, particularly Russ Tamblyn as Riff, and Oscar winners Rita Moreno and George Chakiris as Anita and Bernardo. Chakiris is especially effective as a passionate and very dangerous angry young man, conjuring images of James Dean; it is a mystery that his subsequent film career amounted to nothing. Natalie Wood's performance of Maria is sometimes criticized for her vocal dubbing by Marni Nixon and her in-again out-again Puerto Rican accent, but her dancing is splendid in the "I Feel Pretty" number and she does a spectacular job in the dramatic scenes (although her character is strangely unmoved by the murder of her own brother), particularly the powerful final scene. For all its faults, West Side Story is a stunningly moving film, which is a rare accomplishment for a musical.

1962 was one of the more memorable years in film history, and the classic Best Picture nominees in To Kill a Mockingbird, The Longest Day and The Music Man might all be sure things in any other year (final nominee Mutiny on the Bounty was a mediocre entry that found a place in the final five only because of the deep pockets of the MGM PR department). The year also boasted such classic non-nominees as The Miracle Worker, David and Lisa, The Manchurian Candidate, Through A Glass Darkly and Lolita, any one of which might have taken the Oscar if they had been released in the far weaker 1963. But even against competition like this, there was no contest in the Best Picture race. David Lean’s compelling biography of soldier/author T. E. Lawrence was that rare epic that succeeded in dazzling the senses with pageantry while never losing sight of the intimate human story it told. The film is not perfect – it tiptoes around Lawrence’s homosexuality, and the casting of non-Arab actors like Alec Guinness and Anthony Quinn (who wears a prosthetic nose that is laughably phony) is no more believable than Paul Muni and Luise Rainer playing Chinese peasants in The Good Earth - but it is so skillfully made and so brilliantly acted (especially by nominees Peter O’Toole –who had the bad luck to give his greatest performance the same year that Gregory Peck had both sentiment on his side in addition to his own career-defining performance as Atticus Finch in To Kill a Mockingbird - and Omar Sharif as Sherif Ali ibn el Kharish - who had the bad luck to give his greatest performance in a year when the Academy showed appalling taste in the Best Supporting Actor Award) that one forgets its flaws and mammoth length (it is the second longest film to win Best Picture after Gone With the Wind) and is completely swept away by storytelling in the grandest of manners.

1963 was one of the worst years in film history, with very few films rising above the status of mediocre. In this weak mix, it’s not surprising that Tom Jones won almost all of the year-end awards. Based on Henry Fielding’s “classic” novel (a classic being, in Mark Twain’s definition, a book people praise but don’t read), the film was praised for its naughty-but-nice sexuality and inventive direction. But its status has fallen badly in the years since its initial release, and what seemed inventive in 1963 now comes off as merely gimmicky. It does boast a collection of madly entertaining performances (especially by Hugh Griffith and Edith Evans, whose Oscar chances were diminished by the fact that she was one of three actresses from the film who were nominated for Best Supporting Actress, a record that is still unequaled), but it is ultimately defeated by a mutually contradictory combination of 60’s pseudo-mod and Masterpiece Theatre stuffiness.

Almost completely overlooked in the nominations was one of the most popular escapist films ever made – literally. The Great Escape was the perfect war movie for a country soon to be embittered by Vietnam – fun, unchallenging, and nobody got killed if they had high enough billing. Even more than in the 50s, America longed for a time of easy answers and the further away we get from World War II, the more black and white that conflict seems (an interred Japanese American would probably take issue with that). The POW camp that The Great Escape took place in was a place of movie fantasy (at time when women living in London couldn’t get silk stockings, James Garner had no difficulty “scrounging” them from his cell; and whereas Alec Guinness was stuffed into a torturous tin box when he had solitary confinement in A Bridge on the River Kwai, Steve McQueen was allowed to play baseball in a relatively spacious, well-lit and airy barracks), but that’s part of the fun of the movie. Though far too unpretentious to be considered for the Academy Award, The Great Escape was certainly the most enduring film made that year and the one that is viewed with the most pleasure today.

My Fair Lady was the theatrical event of the 1950s, and its film version was one of the most anticipated openings since Gone With the Wind. The film didn't disappoint, being a smash hit (although it lost money in its initial release because Warner Bros. was forced to pay a record $5.5 million for the film rights) and still a delight today. With wonderful performances by Broadway originals Rex Harrison and Stanley Holloway (who were cast in the film only after Cary Grant and James Cagney turned the roles down) with equally fine work by Audrey Hepburn, Wilfrid Hyde-White, Gladys Cooper and a pre-Sherlock Holmes Jeremy Brett, director George Cukor brought Lerner & Lowe's musical adaptation of Bernard Shaw's Pygmalion to unforgettable life. But as good a film as My Fair Lady is, it is frequently derided as a terrible choice for Best Picture, because 1964 was one of those years that boasted an unusually large number of Oscar-worthy films. If A Hard Day's Night, The Servant, Goldfinger, The Pink Panther, The Americanization of Emily, The Night of the Iguana or Fail Safe been released in 1963, they all would have been likely nominees for Best Picture and might even have taken home the award. But none of them were nominated in this embarrassment of riches year, which saw Becket, Dr. Strangelove, Mary Poppins and Zorba the Greek compete with My Fair Lady for the top prize.

In the final analysis, any one of the five seems a reasonable choice for the Oscar (if any one of them had been released a year earlier or a year later, they would have swept the awards), but the strongest candidate is Stanley Kubrick's anti-war satire Dr. Strangelove: Or How I Learned to Stop Worrying and Love the Bomb. Nominated for four Oscars (including Peter Sellers' triple-threat performance as the United States President, an English air force officer serving on a US Marine base as part of the "International Officer Exchange Program," and the title role - a character that seems a disturbingly accurate prototype of Henry Kissinger; but not for the equally spectacular work of George C. Scott, Slim Pickins, or most memorably Sterling Hayden as an insane general who lives in fear of the communist infiltration of his "precious bodily fluids"), but failed to take any home. With the Vietnam war waging, some Academy voters might have felt that giving the Oscar to the antiwar Dr. Strangelove to be perceived as a statement on world events, and handing out the trophies to (brilliant) escapist fair like My Fair Lady and Mary Poppins less likely to rile up sensitive agitators. But whatever their rationale for handing out the awards in 1964, it was a helluva year for movies, with something for everyone.

It was back to earth in 1965, another mediocre year for movies that did yield one film that ranks as a genuine event: Robert Wise' mega-smash The Sound of Music, whose unprecedented success started an unfortunate trend for elephantine G-rated musicals that lasted five years (the trend that is, although some of the musicals seemed as though they lasted that long as well). Judging the artistic qualities of The Sound of Music is entirely dependent on each viewer's palette for saccharine-flavored optimism; it ranks as the favorite film to legions of devoted followers and as unwatchable pap to legions more (including madbeast.com). The other nominees for Best Picture were Darling, Dr. Zhivago, The Russians are Coming, The Russians are Coming, and Ship of Fools, all second string entries that can be safely described as rounding out the field. Without any landmark artistic achievements available, The Sound of Music's status as a social phenomenon can be reasonably acknowledged.

1966 was another bland year for films, although there were two legitimate contenders for Best Picture honors that were both based on Tony Award winning plays. Robert Bolt’s A Man for All Seasons first appeared on Broadway in November of 1961 to universal reverence and a respectful appreciation for the depiction of Sir Thomas More's refusal to endorse Henry VIII's divorce from Anne Bolyn by Paul Scofield and ran a successful 637 performances. Edward Albee’s Who’s Afraid of Virginia Woolf? made its debut on the Great White Way the following October and outraged New York theatre audiences with its four-letter vocabulary and contentious depiction of married life and ran for 664. The former seemed like a last gasp of the old vanguard that looked back to ancient history and legends so that the lessons it tried to teach wouldn’t cut too closely, and the latter created a sensation as the voice of a new breed of angry young men who picked up the ills of our contemporary society and stuck them firmly in the audience’s face.

There was no contest as to which would win Best Picture when the films went head to head: the impeccably made A Man for All Seasons was exactly the kind of safe, dull and dispassionate film that the Academy loves to honor, beginning with Cimarron and following through to The English Patient and A Beautiful Mind. It’s a well-made and magnificently acted film, but it is permeated with a high-mindedness which leaves the viewer with something of a detached feeling while watching it. Detached is hardly the feeling one gets when viewing Who’s Afraid of Virginia Woolf?, which carries us along a razor’s edge of marital tension throughout it’s 134 minutes. And while A Man for All Seasons is beautifully acted, the performances in Virginia Woolf are nothing short of explosive, especially by Richard Burton and Elizabeth Taylor doing the finest work of their film careers in roles they seem to have had no business playing. Taylor successfully buried her movie star looks to play the harridan Martha (unlike Grace Kelly in The Country Girl, who merely put on a loose sweater and a pair of glasses) to give a performance of sheer intensity, and the virile and powerful Burton submerged himself in the part of a castrated male trying desperately to put up one last fight (James Mason and Jack Lemmon were the original choices for the role). In a decade when the Academy was only making the safest of choices, Who’s Afraid of Virginia Woolf? was far too much of a ticking time bomb for them to anoint with their highest prize.

In The Heat of the Night was a terrific whodunit that was made important because of the racial aspect of the story that pitted a black Philadelphia homicide detective against a small-town Southern sheriff. The by-play between the two was compelling, and the film features a magnificent performance by Sidney Poitier and an Oscar-winning one by Rod Steiger. In another year, it would be an excellent selection for Best Picture. But 1967 was a year that saw the premiere of two of the most influential films ever made and continue to resonate to viewers while In The Heat of the Night has the musty air of a relic of the 60s about it, despite its message of tolerance that maintains its relevance today. Far more evergreen are Bonnie and Clyde, a classic gangster film made unique by the intricate depiction of its title characters and by its graphic violence and sexuality; and the definitive cinematic examination of youthful alienation, The Graduate. Based on Charles Webb's novel, The Graduate told the story of Benjamin Braddock, who's "a little worried about his future" and made a star out of Dustin Hoffman in the role of a 21 year old everyman who has no idea what direction he should take next (a guest at Benjamin's graduation party who suggests that his future is in plastics is of no help at all). Hoffman was actually a thirty year old Obie winner when he played Braddock, and to take the role he had to turn down another film that he'd already been cast in (The Producers, in which he was to have played the Nazi playwright Franz Liebkind). It's impossible to imagine another actor in the part now even though Robert Redford, Charles Grodin and a 19 year old Richard Dreyfuss were seriously considered for the role; and equally fine work is offered by Anne Bancroft as the infamous Mrs. Robinson, Katherine Ross as Elaine and William Daniels (who is actually only ten years older than Hoffman) as Ben's father. The Graduate won the Best Director Oscar for Mike Nichols (for only his second film after Who's Afraid of Virginia Woolf?), one of the few films to capture that trophy and nothing else. In retrospect, it also should have won for Calder Willingham and Buck Henry's clever and insightful screenplay, Dave Grusin and Paul Simon's unnominated musical score, and the Oscar for Best Picture.

1968 was one of the most tense years in American history, with the Vietnam war at its peak, the country reeling from the assassinations of Martin Luther King, Jr. and Robert Kennedy, and the violent demonstrations that culminated at the Democratic National Convention and Kent State. In such troubled times, it's not surprising that the nation craved escapist fare, and the Academy recognized their tastes, naming an unprecedented four musicals and two comedies as Best Picture in the decade. But they really got carried away in their preference for lumbering, overproduced musicals in 1968, selecting the lead-footed Oliver! as the best film of the year. Oliver!, which reduced Dickens' dark novel into a sugary extravaganza of gaudy production numbers, wasn't even the best musical of the year (that honor surely belonged to Funny Girl) and it now seems ridiculous that this tedious nonsense won the top prize when such memorable films as Planet of the Apes, The Producers, The Odd Couple, Rosemary's Baby and 2001: A Space Odyssey weren't even nominated.

Selecting a "best" from this diverse group is difficult (none of the actual nominees Funny Girl, The Lion in Winter, Rachel, Rachel and Romeo & Juliet would probably make the final five today, although all were markedly superior to Oliver!), but the award should have gone to the sublime and original 2001: A Space Odyssey. Stanley Kubrick's masterpiece received four nominations, including Best Director and Best Original Screenplay, but it was overlooked in the Best Picture race and wound up winning only a single award, for its groundbreaking special effects. The Academy never had much use for science fiction, nominating only Star Wars and E.T. for its top prize, but 2001: A Space Odyssey took a genre whose trademarks had been ray guns and hubcaps that passed for flying saucers and transformed it into something sublime. The American Film Institute ranked it number 22 of its 100 greatest films (no other film from this year made the list), and for the Academy to prefer the trivial Oliver! over this landmark film shows just how vapid the tastes of their membership were at the time.

After selecting a G-rated musical for Best Picture in 1968, the Academy did a 180º turn in 1969, awarding an X-rated drama about a New York street hustler. Midnight Cowboy was a brilliant film for its time, featuring remarkable performances by Jon Voight and Dustin Hoffman (who was robbed for the Best Actor Oscar as the Academy turned the award into a sentimental testimonial for John Wayne), but it now seems badly dated, in part because of the many derivative rip-offs it has spawned over the years. Far fresher and more watchable is Butch Cassidy and the Sundance Kid, George Roy Hill's deconstructionist western that began the trend for "buddy" movies that continues to this day. Paul Newman and Robert Redford's chemistry is so easy that it's surprising to learn that the role of the Sundance Kid was originally offered to Warren Beatty and Marlon Brando, neither of whom wanted to accept second billing to Newman. It's doubtful that the film would have succeeded as well with that casting, since anyone who's seen Ishtar or The Countess from Hong Kong know that comedy is not either of those actor's forte.