13 Best Classic Movies on Prime Video (September 2026): ‘The Great Escape’ and More

No one escapes the Stalag Luft III prisoner-of-war camp — at least, that’s how the Germans intended it to be. But their Allied prisoners have other things in mind. Led by Captain Virgil Hilts (Steve McQueen), a motley crew of American, British, and Australian prisoners band together to dig three tunnels underneath the prison and escape in the dead of night. But things don’t go according to plan, and Hilts and the rest of his men will have to readjust quickly if they want to pull off their great escape.

One of the greatest World War II movies of all time, The Great Escape is based on fact … kinda. There really was a daring escape at Stalag Luft III in 1943, although it was executed with less panache than the one in the film version. That doesn’t diminish the film’s entertainment value, which still packs a punch after all these years. McQueen became an international star with the film, and it’s easy to see why. If you had to be locked up with anyone in this world, it might as well be him.

Kate Miller (Angie Dickinson) loves her husband, but he’s bad in bed, and she’s hot to trot. That’s why she does something wild – she has sex with a stranger after a solo holiday visit at a NYC museum. But Kate’s dalliance proves costly as she’s brutally murdered by a strange woman in a black trench coat. Who killed Kate? Her dorky teenage son, Peter (Keith Gordon) and savvy sex worker Liz (Nancy Allen) want to find out, and the answer may lie with Kate’s psychiatrist, Dr. Robert Elliott (Michael Caine).

One of the defining thrillers of the 1980s, Dressed to Kill is violent, explicit and surprisingly funny. Only director Brian De Palma could blend all those disparate elements and make it work, crafting a stylish suspense flick that’s delightfully titillating – and shocking for all the right reasons. Caine’s great as the cagey shrink, but it’s Allen and Gordon who steal the show as the most unlikely crime-solving duo ever.

J.C. Wiatt (Diane Keaton) has it all – a great job, a nice NYC department and a partner who is just as much of a workaholic as she is. But when she inherits her dead cousin’s baby, Elizabeth (Kristina and Michelle Kennedy), she experiences a crash course in a role she never imagined for herself – a mommy. The career-obsessed J.C. can do almost anything, but can she balance fine-tuning her corporate spreadsheet with changing Elizabeth’s dirty diapers?

Yes and no. Baby Boom is a comedy about a career woman who becomes humbled by motherhood, but it never feels retrograde. J.C. discovers she can have it all, but her cutthroat job won’t let. Instead, she finds inspiration – and love – in the Vermont countryside, where she comes into her own as a single mother. Baby Boom isn’t all that realistic – a woman like J.C. would be too addicted to the hustle and bustle of NYC to ever truly leave it – but it offers a fantasy a lot of people want and can’t have: being your own boss and owning a fabulous house in the country. Now that’s a dream worth having a baby for.

Middle-aged widowers Frank (Henry Fonda) and Helen (Lucille Ball) weren’t looking for love, but they found it with each other, even though they both share the same secret – they both have children. Lots of them. As their romance becomes more serious, they both have to decide if it’s worth risking the ire of their combined 18 (!) children to marry and become one big, unhappy family. How will a family that large work? And is there a house big enough to fit them all?

Later remade with Steve Martin and Bonnie Hunt in 2005, Yours, Mine and Ours makes the most out of its exaggerated concept. Fonda and Ball are sweet together as late-in-life lovers who want a second chance at happiness, even if their children aren’t all that accepting of their relationship. Believe it or not, the film is based on a true story; there really was a blended family of 18, and the real Helen had two more kids after her marriage to Frank.

When his wife and son leave him all alone in his New York City apartment for a couple of weeks, middle-aged executive Richard Sherman (Tom Ewell) at first doesn’t know what to do with himself. That quickly changes when he encounters The Girl (Marilyn Monroe), an unnamed actress and model who just moved into the apartment above Richard’s. He becomes so enamored with her that he plots to befriend and seduce her before his family comes back. Richard has a nasty case of the seven-year itch, and he’s too weak not to scratch it while he has the chance.

While outdated, The Seven Year Itch is a fun comedy about temptation, both carnal and comedic. This is the film that contains the iconic scene of Monroe’s white dress being raised by a passing subway below her, but she’s more than just a sex object – she’s also an adept physical comedienne. It’s hard to play dumb, but Monroe is effortlessly appealing as an object of desire who just wants to talk to men instead of sleep with them.  

To life! The Oscar-winning classic Fiddler on the Roof fiddles its way onto Prime Video this month, and it’s always a great time to watch or rewatch one of the best movie musicals of all time. In turn-of-the-20th-century Russia (now Ukraine), Tevye (Topol) is a simple Jewish milkman with a loving wife, Golde (Norma Crane), and five daughters. Things get complicated when several of his daughters fall in love, and Teyve, as custom dictates, must either bless their unions or forbid them from happening. But the old ways are slipping away, and soon, the entire family must reckon with changes that could separate them forever.

Based on the hit 1964 Broadway musical, this film adaptation of Fiddler on the Roof doesn’t feel stagey at all – in fact, you wonder how they even set this epic story of faith, family and Jewish identity in a theater in the first place. Credit cinematographer Oswald Morris, who won an Oscar for his efforts, and director Norman Jewison for giving this simple tale the grand, historical canvas it deserves. As Tevye, Topol is unforgettable, depicting a man too stubborn to change but too sympathetic to be stuck permanently in the past. The songs are still catchy, with gems like “If I Were a Rich Man” and “Sunrise, Sunset” still toe-tappingly good after all these years.

Harry Caul (Gene Hackman) is good at his job. As a surveillance expert working in San Francisco, he’s the best there is at spying on others who don’t want to be spied on. When he accepts a job to record an adulterous couple who meet at a crowded park, he thinks it’s just another routine cheating spouse gig. But when he starts to suspect his subjects could meet a grisly end, he tries to stop the tapes from getting in the wrong hands. Much to his dismay, Harry discovers he may be too late to save them — or himself.

A classic paranoid thriller made at the height of the Watergate scandal, The Conversation is simple yet unsettling. Its sole focus is on Harry and his growing obsession that someone is listening to him as he listens to others. Is it all in his head? Or are there really people out there in the dark tracking his movements? Director Francis Ford Coppola creates a vivid and tense mood of fear and suspicion, one that feels of its time yet also strangely relevant for today’s conspiracy-obsessed populace.

If you ask someone what one of the funniest movies ever made is, chances are they’ll mention A Fish Called Wanda. And with good reason – the 1988 film remains a laugh riot today, and it’s a terrific heist picture to boot.

Jamie Lee Curtis stars as Wanda Gershwitz, an American con artist who helps her boyfriend Georges (Tom Georgeson), Otto (Kevin Kline) and Ken (Michael Palin) rob a bank. They succeed, but when Georges is arrested, Wanda has to seduce a barrister, Archie (John Cleese), to free him – or at least find out where he stashed the loot so she can ditch him and take the money for herself. Nothing goes according to plan since Wanda falls in love with Archie, which enrages Otto, who is in love with her.

In 1947, four German judges stand accused of crimes against humanity. Their crimes? They willingly assisted the Nazis in carrying out laws that targeted Jewish people and anyone who helped them avoid capture. American prosecutor Tad Lawson (Richard Widmark) wants to send them all behind bars for life, convinced their guilt is plain to see. But the trial’s presiding judge, Dan Haywood (Spencer Tracy), isn’t so sure anyone wants to acknowledge what’s plainly evident to him — that many Germans turned a blind eye to the horrors around them, with many actively participating in Adolph Hitler’s quest to conquer Europe. As he gets to know Madame Bertholt (Marlene Dietrich), the widow of a German general and owner of the home he’s staying in, he begins to understand how a civilized nation like Germany could let the Holocaust take place, and what must be done to prevent it from happening again. 

A fictionalized account of the Nuremberg trials, Judgment at Nuremberg presents a somber post-WWII accounting of an event the world was still trying to process a mere 16 years after it officially ended. Director Stanley Kramer isn’t known as a cinema stylist, so expect a lot of stagey scenes with little camera movement and quick editing, but the subject matter is resonant enough to keep you watching. The film boasts an all-star cast, with the two stand-outs being Oscar nominees Judy Garland and Montgomery Clift as victims of Nazi war crimes. 

Did you know that every time a bell rings, an angel gets its wings? If you don’t, then you haven’t watched It’s a Wonderful Life. The 1946 movie is still a holiday movie staple nearly 80 years later, and that’s due to the timeless nature of its story.

It’s Christmas Eve in the idyllic small town of Bedford Falls, but George Bailey’s (James Stewart) life is far from perfect. He’s spent most of it sacrificing his happiness to help others, and all he’s received in return is one misfortune after another. He thinks suicide is his only option left, but a mysterious man named Clarence is determined to show him what a wonderful life he has and how much he’ll be missed if he dies.

It’s a Wonderful Life is a surprisingly dark Christmas tale — after all, Home Alone and Love Actually don’t have suicide as a major plot point. But that’s the key to Frank Capra’s classic: it shows George at his lowest so that his redemption at the end is all the more impactful. The movie also contains one of legendary actor James Stewart’s finest performances. Simultaneously hopeful and cynical, his George is an American Everyman constantly weighed down by life, but never beaten by it.

Joe Buck (Jon Voight) is a dreamer. As a dirt-poor cowboy with no money and a poor education, dreams are all he has. He treks to New York City to become a well-paid gigolo for high-class Manhattanites, but all he finds are other people like him – delusional, desperate and lost. He eventually meets and befriends someone worse off than him – Ratso Rizzo (Dustin Hoffman), a con man with a bad limp and an even worse cough. Together, they find reluctant comfort in a city that keeps on rejecting them. Ratso thinks they can make it big in sunny Miami, but can they scrape enough money together to leave a Big Apple that’s rotten to the core?

It’s astonishing to look back and wonder how an X-rated movie about a male hooker and his sleazy pimp won Best Picture at the Oscars in 1970. That just wouldn’t happen now, nor would any major studio release a film as unsparing and bleak as Midnight Cowboy. But it’s one of the great American films of the century, an almost perfect depiction of friendship between two men who have no one else but each other. Voight is terrific as a sensitive stud who gets destroyed by the real world, and Hoffman is equally great as a lowlife who hates everyone he meets, himself included. If you’re not devastated by the last scene, you should check your pulse to see if you’re still alive.

Who needs Jacob Elordi when you have Laurence Olivier? Both actors played Heathcliff in wildly different adaptations of Emily Brontë’s novel, Wuthering Heights, but it’s Olivier who made the character an object of envy for men and desire for women. He’s a hunk with something to say and someone to die for.

Told in flashback, Wuthering Heights chronicles the doomed romance between Heathcliff and Cathy Earnshaw (Merle Oberon), who began as childhood friends before becoming teenage sweethearts. But Heathcliffe is an orphan from the lower class, and high-class women like Cathy are supposed to marry men like the stiff and boring Edgar Linton (David Niven). Is Cathy and Heathcliff’s love for each other strong enough to cross Britain’s rigid 19th-century social divides?

If you’re looking for a faithful adaptation of Brontë’s novel, look elsewhere. But if gothic romance is your vibe, then this Wuthering Heights will make you wither in delight. Olivier nabbed his first Oscar nomination for his charismatic, matinee idol performance, while Oberon is suitably pale and tragic as the constantly near-death Cathy. 

Right from the get-go, you know novelist Janet Frobisher (Bette Davis) is no good — she confesses to killing her deadbeat husband to his partner-in-crime, George Bates (Gary Merrill). But she’s still the least despicable person in Another Man’s Poison, an unusual noir set in the English countryside. She wants to get rid of George, too, but he’s smarter and deadlier than her now-deceased husband. She’ll have to use her imagination, plus some very convenient poison lying around, to dispose of George so she can be with her younger lover. But the best laid plans often go awry, and in Janet’s case, have fatal results.

Another Man’s Poison isn’t a top-notch thriller — its overcomplicated plot weighs it down just as much as a dead body in a lake. But what it does have is Davis, who acts and acts and acts some more, and leaves no pause silent and no glance unsubtle. She’s a force of nature, and she single-handedly makes this movie electric. Stay tuned for the finale, which involves one of the great switcheroos in the genre.