95 Years of Oscars: Ranking The Best Picture Winners Part Two – #75-51 (2023)

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Welcome to Part Two of our countdown of the greatest Best Picture winners of all time! In Part One, we delved into the assorted range of films that have won this coveted prize through the 95 years of Oscar. Measuring impact, enduring legacy, and overall quality of films, the first portion of the list revealed how some of Hollywood’s earliest ventures struggle to hold up all these years later.

In Part Two, we continue our journey through the annals of Oscar history to celebrate the classics that have captivated audiences and stood the test of time. From timeless films to groundbreaking works of art, these movies have left an indelible mark on the cinematic landscape. Part Two of the discussion highlights a recurring theme: the prevalence of good movies surpassing truly great ones. While there are certainly understandable and commendable winners, the list also sheds light on the Academy’s glaring omissions, where deserving films each year were overlooked.

So, grab your popcorn, settle into your seats, and join us as we unveil the next set of Best Picture winners that have taken their place among the titleholders.

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75. A Man for All Seasons (1966)
Summary: Like Gandhi and Chariots of Fire, A Man For All Seasons is another British history lesson. A tale of political corruption, the film stars Paul Scofield as Sir Thomas Moore who goes up against Robert Shaw as King Henry VIII. The former would win the Oscar for Best Actor. One could argue I am underrating Fred Zinneman’s film a bit here. Costume dramas have long been a tough watch for me – often buttoned up too tightly with overstuffed pageantry and an exhausting air of elitism – and it feels like more of the same with A Man for All Seasons.
What it beat: Alfie, The Russians Are Coming The Russians Are Coming, The Sand Pebbles, Who’s Afraid of Virginia Woolf?
Hindsight’s a bitch: While the performances in Who’s Afraid of Virginia Woolf? make it a fine choice for the best film of 1966, Sergio Leone’s western magnum opus, The Good, the Bad and the Ugly, is the film that will likely be celebrated longest.

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74. Nomadland (2020)
Summary: Frances McDormand stars as Fern, a woman living in her van after her husband’s death and a recession hits her town hard. Joshua James Richards’ masterful cinematography shines in this intimate film, which transcends the portrayal of the bleak nomad lifestyle and instead delves into a captivating character study. Through the lens of a free-spirited woman searching for her rightful place in a world that seems to have discarded her, the film gracefully captures her resilience and inner journey.
What it beat: The Father, Judas and the Black Messiah, Mank, Minari, Promising Young Woman, Sound of Metal, The Trial of the Chicago 7
Hindsight’s a bitch: At the time, I named Lee Isaac Chung’s Minari the best of 2020, which will always be remembered as the year of Covid. Since then, the two movies that seem to have hung around my mind the most are Judas and the Black Messiah and Sound of Metal. Take your pick among those three in what was a slightly below average year for film, during the peak of Covid-19 uncertainty.

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73. Braveheart (1995)
Summary: Braveheart, Mel Gibson’s tale of William Wallace – a 13th century warrior who united Scotland against the British for their independence – is a huge film with incredible action sequences, an emotional love story, and a few technical wonders. It’s a violent spectacle that hasn’t held up well with historians and critics alike and is often confused as a vanity project for Gibson.
What it beat: Apollo 13, Babe, The Postman, Sense and Sensibility
Hindsight’s a bitch: I might be in the minority that still thinks Braveheart was the best film of those five nominees. I understand the historical inaccuracies and the Mel Gibson factor, but Braveheart remains a thrilling and entertaining epic for me. How the Academy missed on Michael Mann’s Heat, however, is beyond me. One of the great crime dramas ever made, Heat gave us an incredible ensemble where each character is given depth and complexity that aid in the high-octane intensity of the onscreen narrative. Heat is a gritty and meticulous cat-and-mouse thriller that continues to find a new audience. This should have been an easy choice.

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72. Wings (1927)
Summary: The first Best Picture winner was also the only silent film to win the award until The Artist won 84 years later. Full of innovative flying scenes, dogfights, strung-out love triangles, and set against the backdrop of World War I, Wings still holds up well nearly a century later. The film rocketed “It-Girl” Clara Bow into household name status and helped lift Gary Cooper’s career off the ground.
What it beat: The Racket, 7th Heaven
Hindsight’s a bitch: Wings was a fine choice to represent the very first Academy Awards. Interestingly, the Academy sidestepped one of the most influential films ever made, The Jazz Singer. The first “talkie” did receive an honorary award for its pioneering, but – as depicted in Singin’ in the Rain years later – there was probably still a lot of hesitation around the advent of sound in films.

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71. The King’s Speech (2010)
Summary: Tom Hooper’s winner is an inspirational true story about how a speech therapist, Lionel Logue (Geoffrey Rush), helped England’s King George VI (Colin Firth) overcome a lifelong speech impediment. This is another Weinstein victory, as we will see happen several times throughout the countdown when the film most remembered loses out to a safe, traditional replacement. Still, not a bad winner. With impeccable period detail accompanied by a few great performances, The King’s Speech is a crowd-friendly, uncomplicated film with a big heart. Nothing wrong with that.
What it beat: Black Swan, The Fighter, Inception, The Kids Are All Right, 127 Hours, The Social Network, Toy Story 3, True Grit, Winter’s Bone
Hindsight’s a bitch: The King Speech is another respectable choice by the Academy, though not one I agree with. Several films from 2010 would rank ahead of the Best Picture winner on my own list. I would be between Inception – Christopher Nolan’s time bending adventure – and The Social Network – David Fincher’s masterpiece, with the latter being the era’s zeitgeistiest film.

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70. Rain Man (1988)
Summary: Featuring my personal favorite Tom Cruise performance, Rain Man is a delightful and sentimental film about two brothers reconnecting and reconciling. Dustin Hoffman gives an all-time virtuoso portrayal as an autistic man who learns to count cards, recollect his past, and discover that Kmart sucks on a road trip with his estranged and materialistic brother.
What it beat: The Accidental Tourist, Dangerous Liaisons, Mississippi Burning, Working Girl
Hindsight’s a bitch: The 1988 Oscars were the first that I remember watching, so Rain Man will always be a sentimental favorite of mine. Some other strong choices from 1988 include Bull Durham, Die Hard, and Big, but none of those seem up the Academy’s aisle (at least at that time). Rain Man is a moving and lighthearted buddy film with two outstanding performances from Dustin Hoffman and Tom Cruise. Their onscreen chemistry and the heartfelt, transformative journey they take together helps Rain Man hold up to this day.

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69. Argo (2012)
Summary: Argo was simply a good, old-fashion style of studio filmmaking that, like Braveheart, took plenty of liberties with fact and fiction to make for a more entertaining homage to Hollywood. Lines of historic moments are blurred in Ben Affleck’s dramatization of the rescue of diplomats during the Tehran hostage crisis of 1979. But who’s complaining? Argo swept the awards season like few have before and is an extremely rewatchable movie.
What it beat: Amour, Beasts of the Southern Wild, Django Unchained, Les Misérables, Life of Pi, Lincoln, Silver Linings Playbook, Zero Dark Thirty
Hindsight’s a bitch: Another very strong year for movies, I can’t fault the Academy for their choice here. Steven Spielberg’s Lincoln or Kathryn Bigelow’s Zero Dark Thirty would each have made for exceptional winners. Paul Thomas Anderson’s The Master is regrettably missing from the nominees above, as is a genre favorite of mine from 2012: Rian Johnson’s imaginative and sensational Looper.

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68. Terms of Endearment (1983)
Summary: Based on the Larry McMurtry book, Terms of Endearment is more than just the epitome of a tearjerker. It is an often-hilarious look at the love that prevails within a dysfunctional family. Shirley MacLaine and Debra Winger star as a mother and daughter who are consistently at odds with each other. Their polarizing relationship is amplified by the unstable men in their lives (Jack Nicholson, Jeff Daniels, John Lithgow) until the famously tragic plot twist changes everything.
What it beat: The Big Chill, The Dresser, The Right Stuff, Tender Mercies
Hindsight’s a bitch: Terms of Endearment is a good choice. You can’t fault Academy voters for how the film tugged at their heartstrings. My preference that year is The Right Stuff. With the same sense of dauntless grandeur that First Man would invoke 35 years later, The Right Stuff’s sheer magnitude, cinematic vision, and remarkable attention to detail would have been enough to secure my vote.

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67. Shakespeare in Love (1998)
Summary: As it was often the case with Best Picture winners of the late 1990s through early 2010s, the grip that Harvey Weinstein had on the Academy is now clear and obvious. It was never more apparent than in 1998.
What it beat: Elizabeth, Life Is Beautiful, Saving Private Ryan, The Thin Red Line
Hindsight’s a bitch: There are some tremendous choices in the lineup, so I won’t overly nitpick the Academy’s decision to go with the sweet and whimsical love story. Shakespeare in love is funny and intelligent. But either of the two war films would have been much stronger choices. The fact that they were up against each other might have been what sealed their fate, as I still have a hard time deciding which one I prefer over the other. For the harrowing opening sequence on Omaha Beach, I’d suppose I’d have given it to Saving Private Ryan.

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66. Gandhi (1982)
Summary: Richard Attenborough’s Gandhi is about as good a historical biopic as you will find, cemented by one of cinema’s all-time great performances by Ben Kingsley. And we all know how much the Academy loves their biopics.
What it beat: E.T. The Extra Terrestrial, Missing, Tootsie, The Verdict
Hindsight’s a bitch: I am a big fan of Richard Attenborough’s Gandhi, and an even bigger fan of Ben Kingsley’s performance as the Mahatma. But holy moly, what a year for science fiction! Perhaps no year better calls out the Academy’s past bias against the genre. First, you have an all-time great with E.T. losing Best Picture. But also wrap your head around two huge, classic sci-fi flicks that weren’t even nominated: Ridley Scott’s Blade Runner and John Carpenter’s The Thing. It would have been a great year to recognize the genre and to celebrate one of Hollywood’s brightest stars, Steven Spielberg.

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65. Million Dollar Baby (2004)
Summary: Clint Eastwood’s second Best Picture winner is a far more melancholy film than the movies he made earlier in his career. What starts off as a typical, underdog boxing narrative quickly takes a left turn into something entirely different. It’s an authentically earnest film about desperate and failed characters looking for humanity and salvation from each other, both inside and out of the ring.
What it beat: The Aviator, Finding Neverland, Ray, Sideways
Hindsight’s a bitch: I have no qualms with Million Dollar Baby winning Best Picture. As much as I enjoy Sideways, I think Clint Eastwood’s boxing flick is the best of the nominees. Here’s where I probably have a differing opinion than 99% of you: Mel Gibson’s The Passion of the Christ was the best movie of 2004. I’m sure I’ll take heat for saying this, but Gibson’s film inspired intense debates and stands out for its remarkable artistic and technical achievements. While the scenes we are witnessing are graphic and difficult to watch, there’s no denying the immersive experience that Passion brought to the screen. It’s as valid and visceral as any biblical story that’s ever been captured on film. Say what you will about Gibson as a person, I make no defense for the things he has said and done, but it’s hard for me to deny the outstanding filmmaker he became. Still with me?

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64. Ordinary People (1980)
Summary: Robert Redford’s Ordinary People is a restrained yet powerful film about how grief is handled differently by members of a family who experience an unimaginable tragedy. What makes Ordinary People special is how it treats mental illness and depression with sincerity and relatability. Donald Sutherland, Timothy Hutton, Mary Tyler Moore, and Judd Hirsch all give extraordinary and moving performances.
What it beat: Coal Miner’s Daughter, The Elephant Man, Raging Bull, Tess
Hindsight’s a bitch: Ordinary People is a fine choice for Best Picture in most years. The problem with giving it the prize in 1980 is that Martin Scorsese’s masterpiece – Raging Bull – was right there. Raging Bull not only should have won, but if it did, it would have been in the top 10 on this list.

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63. Mrs. Miniver (1942)
Summary: William Wyler’s Mrs. Miniver – set during the second World War – is the first Best Picture winner to be about the global tragedy. Greer Garson and Walter Pidgeon star as a middle-class English couple raising their family at the outset of the conflict, one of the few films to be about a war that was still going on at the time. Because of this (and due to some timely rewrites that seemed intent on increasing American support for the war) the film is regarded by some as light propaganda. It’s another sentimental – yet wholly effective – family drama.
What it beat: The Invaders, Kings Row, The Magnificent Ambersons, The Pied Piper, The Pride of the Yankees, Random Harvest, The Talk of the Town, Wake Island, Yankee Doodle Dandy
Hindsight’s a bitch: Who doesn’t love Mrs. Miniver? The film gets bonus points with me for having Teresa Wright in its cast. IYKYK. Mrs. Miniver is another fine choice that’s hard to argue with. My vote would have gone to Michael Curtiz’s biopic, Yankee Doodle Dandy, starring James Cagney in a career-best performance as musical composer, playwright, actor, dancer, and singer George M. Cohan.

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62. Hamlet (1948)
Summary: Hamlet sometimes feels like it won for its iconic Laurence Olivier performance more than anything else. The film lacks any kind of ingenuity or identity beyond the merits of Olivier’s accomplishments. However, many still consider this to be the categorical Hamlet.
What it beat: Johnny Belinda, The Red Shoes, The Snake Pit, The Treasure of the Sierra Madre
Hindsight’s a bitch: Laurence Olivier’s Hamlet might be the greatest Shakespearean adaptation ever made and is another good choice on the list of Best Picture winners. Like many others on this list, there is just a better option out there. John Huston’s Treasure of the Sierra Madre delivered legendary actor Humphrey Bogart’s greatest performance. The tale of greed and ambition still resonates today as a terrific film.

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61. Gentleman’s Agreement (1947)
Summary: Gregory Peck stars as a journalist who pretends to be Jewish to investigate anti-Semitism in Elia Kazan’s Gentleman’s Agreement. The film was a bit groundbreaking for its time by tackling social issues of racism, even if “message” films often win Best Picture nowadays. The façade adds to a narrative that is both complex and intelligent, and it is a well-meaning film with a big heart even if it comes off a bit puffed up and self-congratulatory today.
What it beat: The Bishop’s Wife, Crossfire, Great Expectations, Miracle on 34th Street
Hindsight’s a bitch: The Academy got it right.

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60. Grand Hotel (1931/1932)
Summary: One of the first star-studded episodic dramas to win Best Picture, Grand Hotel is headlined by silver screen legends Greta Garbo and John Barrymore. The adaptation of the Broadway hit remains the only film to win Best Picture without a single other nomination. That’s a distinction that will probably never be duplicated.
What it beat: Arrowsmith, Bad Girl, The Champ, Five Star Final, One Hour with You, Shanghai Express, The Smiling Lieutenant
Hindsight’s a bitch: The Academy got it right.

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59. Kramer vs Kramer (1979)
Summary: Meryl Streep and Dustin Hoffman are extraordinary in this timely tale of marital divorce and the problematic battles of child custody. The Baby Boomer generation was the first to really experience the cultural movements widespread divorce and reversal of gender roles in the nuclear family.
What it beat: All That Jazz, Apocalypse Now, Breaking Away, Norma Rae
Hindsight’s a bitch: This is a very similar situation to 1980’s Ordinary People beating Raging Bull in the sense that if Apocalypse Now had won, Francis Ford Coppola’s film would have been in my top ten of this list. Kramer vs Kramer is a really good movie, though.

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58. How Green Was My Valley (1941)
Summary: John Ford’s view of the working-class man over the passage of time is nostalgic and convincing. Core values, faith in God, and the importance of doing a good job well are at the center of this dreary and determined drama.
What it beat: Blossoms in the Dust, Citizen Kane, Here Comes Mr. Jordan, Hold Back the Dawn, The Little Foxes, The Maltese Falcon, One Foot in Heaven, Sergeant York, Suspicion
Hindsight’s a bitch: Man, what an incredible year for movies! The list of nominees doesn’t even include two Barbara Stanwyck romantic comedies – Ball of Fire and The Lady Eve – nor Sullivan’s Travels, all top-notch films at their time. As is the theme of Part Two, the winner, while good, beat out one (or in this case several) great films. How Green Was My Valley might best be remembered as the film that beat Citizen Kane, who many argue to be the greatest film ever made. Had Kane won, it might have topped this list. The Maltese Falcon is another enduring showpiece that would have landed much higher on this list, had it won. In their place is John Ford’s melodramatic tale of a coal-mining family, that while fine in its merits of sweeping cinematography, rich storytelling, and emotional depth, is a tad overly sentimental.

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57. All the King’s Men (1949)
Summary: Broderick Crawford stars as Willie Stark, a corrupt Southern politician who rises to the top by selling lies in the slick and powerful All The King’s Men. The character of Stark was based on real-life Louisiana governor and U.S. Senator Huey Long, though we might recognize traits of Stark in more modern-day politicians as well. The point is the song remains the same 75 years later. It’s a fascinating study on the type of firebrands that dominate politics.
What it beat: Battleground, The Heiress, A Letter to Three Wives, Twelve O’Clock High
Hindsight’s a bitch: All the King’s Men is the best of the nominees, but Carol Reed’s The Third Man is one of my personal favorite movies ever made, and the preeminent film noir of all time. How it managed to miss the nomination with a cast that includes Orson Welles, Joseph Cotten, and Valli – along with one of the greatest screenplays ever written (Graham Greene) – is beyond me.

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56. Chicago (2002)
Summary: One of the most fun movies to ever win Best Picture, Rob Marshall’s Chicago delivers all the goods. Renée Zellweger and Catherine Zeta-Jones are incredible as the murderous. pair imprisoned for their wrongdoings. Bob Fosse’s indelible sing-along musical numbers, stunning choreography, and wonderful satire on celebrity and our justice system helped make Chicago the first musical Best Picture winner since 1968’s Oliver, and the only one to do so since.
What it beat: Gangs of New York, The Hours, The Lord of the Rings: The Two Towers, The Pianist
Hindsight’s a bitch: This is a tricky year. The Academy was never going to give Best Picture to the middle installment of The Lord of the Rings, so Chicago is a perfectly fine choice. I am a big fan of Rob Marshall’s musical, even if it does seem hard to say that it is the better film to Roman Polanski’s The Pianist.

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55. My Fair Lady (1964)
Summary: Speaking of musicals, George Cukor’s My Fair Lady remains one of the greatest ever made. It is one of four musicals to win Best Picture in the 1960s. Audrey Hepburn is terrific, and Rex Harrison is incomparable. Adapted from the 1956 stage musical, it’s a “loverly” film.
What it beat: Beckett, Dr. Strangelove: Or How I Learned to Stop Worrying and Love the Bomb, Mary Poppins, Zorba the Greek
Hindsight’s a bitch: Like Chicago, My Fair Lady is a good choice. While the film doesn’t seem to be holding up well with younger generations, it’s hard to hate on Rex Harrison and Audrey Hepburn’s charming performances, Harry Stradling’s gorgeous cinematography, Cecil Beaton’s incredible costume design, and Gene Allen, Cecil Beaton, and George James Hopkins’ outstanding art direction. I would vote in favor of Stanley Kubrick’s Dr. Strangelove, my #1 comedy of all-time.

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54. Mutiny on the Bounty (1935)
Summary: Frank Lloyd’s Mutiny on the Bounty stars Clark Gable as first mate Fletcher Christian and Charles Laughton as the contemptible Captain William Bligh. The film was a huge hit at the box office, and was heavy on action, mysterious settings, clashing drama, and high-seas adventure. This is the first (and best) of several adaptations of the 1932 novel, and the first (and only) time that three actors for the same film were nominated for Best Actor. All three lost to Victor McLaglen (The Informer), and the very next year the Supporting Actor/Actress categories were installed.
What it beat: Alice Adams, Broadway Melody of 1936, Captain Blood, David Copperfield, The Informer, Les Misérables, The Lives of a Bengal Lancer, A Midsummer Night’s Dream, Naughty Marietta, Ruggles of the Red Gap, Top Hat
Hindsight’s a bitch: Literary adaptations were the theme of 1935. With variations of Charles Dickens, Victor Hugo, and William Shakespeare among the nominees, the Best Picture prize went to a film based on a 1932 novel by Charles Nordhoff and James Norman Hall. I agree with the Academy’s choice here, with Fred Astaire’s best film, Top Hat, being a close runner-up.

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53. The Shape of Water (2017)
Summary: Guillermo del Toro’s passion project is more than just a strange and quirky love story between a shy, mute girl and a merman. His avant-garde fairytale also pays homage to the early days of Hollywood, the Cold War, a shared loneliness, and the boundaries society often sets on romance. The meticulous craftsmanship is to be expected in any del Toro film and only adds to the magic spell he puts us under.
What it beat: Call Me By Your Name, Darkest Hour, Dunkirk, Get Out, Lady Bird, Phantom Thread, The Post, Three Billboards Outside of Ebbing, Missouri
Hindsight’s a bitch: The Academy got this right, and I am still kind of surprised by it. A romantic fairytale fantasy film beating out historical dramas (Darkest Hour and Dunkirk), quirky coming-of-age comedies (Lady Bird), and typical Oscar drama (Three Billboards)? Who’d have thought? The Shape of Water winning shows how far the Academy has come on sci-fi/fantasy films in the 21st century.

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52. Everything Everywhere All at Once (2022)
Summary: Our most recent winner is the most atypical and inventive film to win Oscars’ greatest prize in the 95-year history of the Academy Awards. Just about every aspect of the stirring film broke barriers in one way or another. From butt plugs to hot dog fingers to a mostly Asian cast, EEAAO is just a really cool and inspired choice. That alone is worth celebrating.
What it beat: All Quiet on the Western Front, Avatar: The Way of Water, The Banshees of Inisherin, Elvis, The Fabelmans, Tár, Top Gun: Maverick, Triangle of Sadness, Women Talking
Hindsight’s a bitch: Speaking of sci-fi films winning, Everything Everywhere All at Once might have been considered a bizarre choice a couple decade ago. The Academy certainly has diverged from its early days, mostly for the better. While I very slightly preferred All Quiet on the Western Front, EEAAO is a tremendous winner.

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51. The Lost Weekend (1945)
Summary: A somber and honest look at the effects of alcoholism, Ray Milland gives a noteworthy performance as a failed, postwar writer who locks himself in his apartment to try to kick the habit. Billy Wilder shows why he is one of the all-time great directors and screenwriters with one intense and desperate moment after the next. Filled with acerbic and biting dialogue, Wilder and co-writer Charles Brackett’s script is among the best of its time.
What it beat: Anchors Aweigh, The Bells of St. Mary’s, Mildred Pierce, Spellbound
Hindsight’s a bitch: What an incredible year for film noir! Along with Mildred Pierce and Spellbound, To Have and Have Not (my favorite film of the year) makes for an excellent trio in the genre. Billy Wilder’s Lost Weekend is yet another fine choice that is hard to complain about.

That wraps up Part Two in the series, which highlights the intriguing notion that sometimes good films have the power to surpass great films. This is oftentimes dependent of the era (or zeitgeist). As we delve deeper into the rankings of Best Picture winners, we are reminded that cinematic excellence goes beyond technical achievement and critical acclaim. It ultimately lies in the connection forged between the film and its audience, making even good films truly triumphant in their own right.

Get ready for an exciting week ahead as we crack the top 50 Best Picture winners down to 26th!

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