River Phoenix was a prodigy who built a career with some of the most endearing and breathtaking performances imaginable. Phoenix’s talent initially captured the affections of movie fans in the late '80s and early '90s. As a child, Phoenix starred in the likes of Joe Dante’s Explorers and the seminal classic Stand By Me. As Phoenix blossomed into adulthood the roles he started playing seemed to challenge audiences’ expectations and illuminated the adventurous scope of his talent such as the queer drama My Own Private Idaho. But Phoenix’s ascendance in the movie sphere was swiftly cut short by his untimely death in 1993, at the incredibly young age of 23.

Like many young American greats, Phoenix, no less than Buddy Holly, James Dean, or Judy Garland, and others before him, seemed to be taken before his time. It would be difficult not to find some reasonable comparison to James Dean whose career was tragically cut short with his death at 27, with a mere three studio pictures behind him. Phoenix was a beacon of hope to many both on and off the silver screen, and he wanted to make the world a better place, he was an activist for the environment and animal rights, and collaborated with PETA. But the memory of Phoenix lives on with his family and fans and can be discovered by audiences through the legacy of films he’s left behind. Every film Phoenix was in adds another layer or shade to his career. These five films in particular really demonstrate River Phoenix at his absolute best.

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Charlie Fox in The Mosquito Coast (1986)

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Image via Warner Bros.

This is a thought-provoking drama from director Peter Weir and with a script from Paul Schrader (Taxi Driver, Raging Bull, First Reformed) which was released in 1986. Phoenix plays Charlie, the son of Allie Fox (Harrison Ford) an inventor whose disdain for capitalism leads him to bring his family to South America in the hopes of building a Utopia. Phoenix brings a profound warmth and affection to the role, and a distinctive rebelliousness. There’s an undeniable authenticity to Charlie that really illuminates the capacity for Phoenix as an actor to deal with more mature scenes than the likes of Explorers. Phoenix from the get-go holds his own with Harrison Ford. This is evident through the awe and respect Charlie holds for his father in the early scenes in the film such as when they’re riding in a truck and Charlie is eager to agree with his father’s Anti-American sentiments. This is a must-see River Phoenix film because his performance here really foreshadows his later work. Charlie's transition here from childhood to adulthood symbolizes a maturing in Phoenix as an actor.

Indiana Jones in Indiana Jones and the Last Crusade (1989)

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Image via Paramount Pictures

Phoenix is unforgettable as a young Indiana Jones at the beginning of the third Indiana Jones, which was released in 1989. Phoenix excels in the role and brings all the trademark wit and passion for history you’d expect. Young Indy is a boy scout who mischievously breaks away from his scout group in the Utah Canyons and discovers thieves stealing an ancient cross. Indy heroically retrieves the holy relic, and the thieves chase in hot pursuit. It’s a dazzling Spielbergian action sequence that hops and jumps from horseback, to train, and carriage. Phoenix swings and kicks and ducks and dives and shows a real flair for physical action and humor. River Phoenix is literally perfect casting, and brings young Indy to life, and shows how he became the Iconic character we all know and love.

Mikey Waters in My Own Private Idaho (1991)

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Image via Warner Bros.

This is a quirky 1991 coming-of-age road movie directed by Gus Van Sant, shortly after his acclaimed indie break through Drugstore Cowboy. My Own Private Idaho is about a male prostitute, Mike Waters, who loves his best friend Scott (Keanu Reeves), and was abandoned by his mother as a child and sets off to find her. It was a real departure to see Phoenix in a queer role, having mostly played hetero normative roles, but he perfectly inhabits the role, and it’s impossible to imagine anybody else ever playing the role. Phoenix is naturally a highly emotive and very sensitive actor, and he taps into his more effeminate side here as Mike. He brings a real tenderness and emotion to the part mixed with physical comedy and action. This movie is worth it just to see the evolving romance between Phoenix and Reeves’s characters. A scene that really stands out is when Mike admits his longing for Scott in a tender exchange while they camp off-road with only a fire and each other for warmth. There is such an organic simplicity to the scene, it is removed of any profundity what so over, it’s an unfettered exchange of pure emotion, and it’s an absolute masterclass in honest to god acting.

Chris Chambers in Stand By Me (1986)

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Image via Columbia Pictures

This Rob Reiner-directed masterpiece is arguably the best coming-of-age film ever made, and undoubtedly one of the most beloved. The film was released in 1986 and is surprisingly based on a short story ‘The Body’, by acclaimed horror writer/maestro Stephen King. The film recalls the lives of a group of boys in small-town America as they go on an adventure into the woods. Phoenix plays the role of Chris Chambers and gives an iconic performance that immortalizes boyhood and the rites of passage to manhood. This is a stand-out role in Phoenix’s film catalog and the performance was to define the rest of his career.

Danny Pope in Running on Empty (1988)

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Phoenix received an Academy Award nomination in 1989 for his performance as Danny Pope in this phenomenal Sidney Lumet directed drama about a fugitive family on the run in the US. The role of Danny led to Phoenix becoming the sixth-youngest person nominated for best-supporting actor. Danny’s parents are being continuously pursued by the government for an act of political activism. So just as Danny begins to get used to a town and make friends he’s uprooted and has to flee. It’s all he’s ever known and Danny strives for a normal family life and childhood. He has an acute interest in piano and is encouraged to pursue college. But Danny’s parents can’t send him to college and keep the family together. Danny is forced to choose between his family and his future. The film also stars Judd Hirsch and Martha Plimpton (who became Phoenix’s girlfriend off-screen). There are such tender, magnetic exchanges between River and Martha, as Danny discovers the joys and pain of first love, the beach scene is a great example of this. This is an empathetic and detailed character-driven script directed by one of the greatest American directors of all time. Seeing Phoenix collaborating with Lumet certainly marks a significant moment in his artistic and professional career, and is arguably the best work Phoenix has ever done which more than merits its place at the top of this list.