As the old saying goes, “they don’t make them like they used to.” There’s just something extremely special about classic movies. I wouldn’t go as far as to say that movies were better back then (I love plenty of modern films), but I adore watching films released decades before I was even born.
When it comes to classic movies (and I do mean classic here), Prime Video has always been one of the best streaming services for finding legendary flicks from the Hollywood of yesteryear. Case in point, the platform’s June 2026 slate includes some truly legendary movies. I’m taking films that have influenced generations of filmmakers and still do even today.
If you also have an appreciation for classic movies, and find anything presented in stunning black-and-white very much a positive rather than a stumbling block. Here are the five classics to watch on Prime Video now.
‘12 Angry Men’ (1957)
Forget daredevil stunts or special effects. Director Sidney Lumet proves that all you need to craft an enthralling movie is an incredible script and magnetic performances. “12 Angry Men” is as riveting as it is simplistic in setup, but to quote another old saying, “the simplest ideas are often the best.” This legal drama will have you hooked on every word as its cast of jurors debate whether a young boy committed the murder of his father.
At the heart of the debate is Henry Fonda’s Juror #8 (none of the characters are named, bar two at the very end); initially, he's the sole dissenting voice. His fellow jurors are convinced of the boy’s guilt without need for discussion, and it’s Fonda’s job to convince them to at least consider the fact before sending the defendant to the electric chair. Set in a sweltering New York City courthouse, “12 Angry Men” is more engrossing than basically any modern crime drama. It’s a true cinematic masterpiece.
Watch "12 Angry Men" on Prime Video now
‘Paths of Glory’ (1957)
No surprise to see a Stanley Kubrick movie on this list; the director was a true master of the cinematic craft. While I wouldn’t go as far as saying “Paths of Glory” is overlooked, it doesn’t get the same modern-day attention that some of Kubrick’s other movies do, so if you’ve neglected to watch this war drama until now, that’s an error you should correct. Next to “All Quiet on the Western Front,” it’s one of the most sobering anti-war pictures ever created, with Kubrick sharply portraying the futility of conflict and the human cost.
Set during World War I, a French general seeking personal glory (Adolphe Menjou) orders his men to commit to a near-impossible offensive mission. When the doomed-from-the-start plan fails and the soldiers retreat, it’s decided that three of the platoon should be court-martialed to save face. In steps Colonel Dax (Kirk Douglas) to act as the case for the defense, arguing no man should pay the ultimate price for the foolishness of their superiors.
Watch "Paths of Glory" on Prime Video now
‘The Apartment’ (1960)
“The Apartment” is probably my favorite romantic comedy of all time. It’s the ultimate feel-good watch, and a movie I’ve turned to on more than one occasion when in need of a mood-booster. Like any good rom-com, its greatest strength is the chemistry between its leads, Jack Lemmon and Shirley MacLaine. Within moments of meeting them, you’ll be rooting for their characters to figure out their baggage and just be happy together. Clearly, plenty of awards voters got swept up in their romance, as the Billy Wilder movie took home Best Picture at the 33rd Academy Awards.
“The Apartment” centers on a browbeaten insurance worker named C.C. Baxter (Lemmon), who reluctantly allows his bosses to use his Upper West Side apartment as a hook-up pad for their extramarital affairs. When company bigwig Mr. Sheldrake (Fred MacMurray) uses the apartment to liaise with elevator operator Fran (MacLaine), Baxter is heartbroken as he’s deeply infatuated with Fran himself. What follows is a charming romantic comedy-drama as Baxter tries to win the girl while also climbing the treacherous corporate ladder.
Watch "The Apartment" on Prime Video now
‘West Side Story’ (1961)
Earlier this week, I gave some much-deserved love to Steven Spielberg’s 2021 “West Side Story,” so it’s only fitting that now it’s the turn of the first feature adaptation of the Broadway show. Nominated for 11 Oscars and winning 10 (including Best Picture), this 1961 all-singing, all-dancing musical is bursting with flair and is fortunate enough to be scored by some of Stephen Sondheim’s best work. Even non-musical enjoyers should give it a shot.
If you somehow didn’t know, “West Side Story” is based on Shakespeare’s most renowned work, “Romeo and Juliet,” but rather than being set in Verona, Italy, the story of two star-crossed lovers is transported to ‘50s New York. Maria (Natalie Wood) is the sister of the leader of a street gang named the Sharks, while Tony (Richard Beymer) runs with their rivals, the Jets. Despite belonging to opposite sides of an ongoing turf war, they meet and fall in love, but as you probably know, tragedy is awaiting.
Watch "West Side Story" on Prime Video now
‘Midnight Cowboy’ (1969)
Another Best Picture winner, “Midnight Cowboy" was a controversial movie upon its release. It was even branded with an X-rating (the equivalent of an NC-17), which could have sunk its chances of success out of the gate. However, the movie’s quality, and even the backlash itself, served only to heighten interest, and it went on to be an awards favorite. And even if you’ve never seen “Midnight Cowboy,” I bet you’ve heard (and probably used yourself) its most iconic line, “Hey, I’m walkin’ here!”
Texan Joe Buck (Jon Voight) heads to the bright lights of New York City with plans of making his fortune. However, making big bucks in the big city proves to be tougher than he’d expected, and he finds himself homeless, making friends with a street rat named Ratso (Dustin Hoffman). The two come to rely on each other to survive as they roam the streets and look for a hustle that might turn their fortunes around for good.
Watch "Midnight Cowboy" on Prime Video now
