As River Phoenix’s final film receives a belated release 19 years after his tragic demise, I thought it fitting to celebrate, arguably, the finest actor of a generation.

There is a natural tendency, when somebody famous dies tragically young, to lionise them, to overstate their accomplishments, exaggerate their potential. When they’re also a soulful-eyed, walking pair of cheekbones, the temptation to canonise and eulogise the deceased becomes ever stronger. James Dean was a fine actor, but in terms of his performances, there’s nothing there that his contemporaries – and heroes – Marlon Brando and Monty Clift didn’t do better. Jim Morrison may have done us all a favour by posthumously soundtracking that bravura opening to Apocalypse Now, but The End also contains the lines: “Ride the snake to the lake … He’s old, and his skin is cold.”

River Phoenix, though, really was as good as his cheerleaders would have you believe: an actor of deceptive range, unexpected comic ability, and unrivaled sensitivity. When he died in 1993, aged just 23, the world of movies lost one of its most important, distinctive and talented performers. Phoenix was a one-off. He could play uncultured grunts, troubled teens or lovelorn hustlers with equal skill, creating enrapturing, indelible characters who lived, and breathed, and tugged at the tear ducts. He could walk off with a movie from under the nose of Harrison Ford (The Mosquito Coast), convince an audience that Keanu Reeves was the most desirable man in the world (My Own Private Idaho) or draw you – against your will – into a deeply silly thriller about Russky spies (Little Nikita). There was something uniquely gentle and vulnerable about him, his emotions always pressing against the surface, and the feeling remains that – had he lived and stayed clean – he could have gone on to do anything.

Born in Oregon and raised in the Children of God movement, Phoenix was encouraged by his parents to begin acting after the family relocated to California. Following his feature debut as a chubby-cheeked, 14-year-old nerd with Dwight Schrute glasses in Joe Dante’s puzzlingly misguided sci-fi, Explorers, Phoenix would quickly establish himself as the most exciting young actor on the planet, delivering a handful of the finest performances ever beamed onto a movie screen. There would be missteps along the way – disposable fare like I Love You to Death and Sneakers, in which he was often the only thing worth watching – but then there were movies like these…

1. Stand by Me (Rob Reiner, 1986)

This seminal coming-of-age film saw Phoenix cast as Chris Chambers, the tender tough guy whose untimely death sparks the narrator’s reminiscences. In only his second movie, Phoenix is simply astonishing, navigating his character’s complexities with consummate ease, and displaying an underrated comic ability – repeatedly, gleefully leading a chorus of “I ran all the way home” to annoy an excited Vern (Jerry O’Connell) – that blends perfectly with his assured handling of the film’s sentimental high-spots. For the pivotal scene, in which Phoenix breaks down in tears whilst recounting his wrongful persecution by a duplicitous teacher, Reiner told his young actor to think of the saddest thing that had ever happened to him. After the director called ‘Cut’, Phoenix continued to weep uncontrollably. Just as that powerhouse sequence is even more potent because you can only imagine what drove it, so the film’s final moments have acquired a haunting resonance in the light of Phoenix’s tragic demise. Surely even away from the prism of history, it would remain a remarkable movie: prime Americana, lent immeasurable weight by Phoenix’s arresting, star-making turn.

2. The Mosquito Coast (Peter Weir, 1986)

An intense domestic drama with a jungle backdrop, Weir’s film contains arguably Harrison Ford’s most impressive and multi-layered characterisation, as an inventor who goes potty in the wild. Phoenix acts him off the screen. The young actor’s gobsmacking gifts – manifested in his affecting narration, a mini-meltdown and a look of abject, unforgettable horror as his father’s instability becomes all too apparent – manage to overcome several sizeable obstacles, including stilted dialogue, an ‘80s hairdo and the fact that he is often to be seen rocking a sleeveless vest. As his father shrieks with anguish at his dreams going up in flames, Phoenix manages to articulate a life-changing epiphany with a few blinks and a close of his mouth, before his troubled narrator is jolted back to his senses by another massive explosion.

3. Running on Empty (Sidney Lumet, 1988)

After a couple of disappointments – A Night in the Life of Jimmy Reardon, which was taken out of its director’s hands, re-cut and re-named, and the daft thriller Little Nikita – Phoenix got back on top with this dynamic drama about a family fleeing from its radical past. Sporting impressively floppy hair, Phoenix landed his first and only Oscar nomination as a teenager whose happiness is constantly compromised by relocation and obfuscation. Playing opposite real-life girlfriend Martha Plimpton (also his foil in The Mosquito Coast), he displays both a ready sense of humour – engaging in some old-fashioned romantic sparring – and a devastating emotional sensitivity. Often to be found at his best when surrounded by foliage (see also: Stand by Me), the scene in which Phoenix, crouching in a garden, comes clean to his girlfriend about his identity makes every hair on the back of the neck stand up. “I just wanted to tell you that I was sorry,” he says, his voice cracking, tears springing in his eyes. The Oscar went to Kevin Kline for A Fish Called Wanda. Naturally.

4. Indiana Jones and the Last Crusade (Steven Spielberg, 1989)

Not a landmark performance, exactly, but just about the most fun you can have with your trousers on: a riotous mini-prequel of a prologue that features Phoenix as the Young Indy and explains how the professor acquired his hat, his scar, his whip and that noted aversion to snakes.

5. Dogfight (Nancy Savoca, 1991)

From Indy to indie: this heartfelt low-budgeter casts Phoenix against type as a Marine with a crew cut, who picks up waitress Lili Taylor the night before heading off to ‘Nam – as he and his pals compete to see who can bring the ugliest date. The script went through numerous revisions (an early draft had Taylor’s character becoming a talkshow host) and the coda still has a notably phony mid-60s atmosphere, but what’s striking is just how effortless the rest of it seems, as two vivid, well-drawn characters embark on a touching romance, their true selves unfolding slowly across an hour-and-a-half, thanks to intelligent writing and a pair of exceptional performances.

6. My Own Private Idaho (Gus Van Sant, 1991)

This, my friends, is the one: a dazzling, dizzying indie masterpiece – loosely based on Shakespeare’s Henry IV – about a narcoleptic rent boy (Phoenix) who stumbles from one absurd, troubling sexual encounter to another whilst searching for his mother and seeing his love for friend and companion Keanu Reeves go unrequited. Wandering into the film armed only with a black bag and a stopwatch, wearing someone else’s shirt, Phoenix’s Mike is one of the great characters of the decade: compelling, beguiling and endlessly endearing, and with a fine line in existential asides (“I always know where I am by the way the road looks. Like I just know that I’ve been here before… I just know that I’ve been stuck here… like this one fucking time before, you know that?”) Boasting fantasy sequences, a slide guitar fetish and a succession of curious comic interludes, it’s a dream-like film, so it seems suitable that its hero should be cursed to dream, often at the most inappropriate of junctures, relying on the kindness of strangers as he floats through life, brought down to earth periodically by sweaty, fat men who want sex. And as with both Stand by Me and Running on Empty, there’s a clear emotional centre: a scene that holds the key to understanding the larger piece. In this case, it’s a campfire chat that begins with some wonderfully absurdist dialogue (“You had a maid?”), before laying bare Mike’s concealed emotions. Buffeted away by Reeves’ contention that “two men can’t love each other”, Phoenix murmurs disconsolately: “I love you and… you don’t pay me.”

The legacy of River Phoenix

Phoenix followed the peerless Idaho with three misfires: Sneakers – Phil Alden Robinson’s strangely underwhelming follow-up to Field of Dreams – the erratic Western Silent Tongue, and a country music drama called The Thing Called Love. He sleepwalked through the latter, ashen-faced, his performance riddled with odd mannerisms – a sad screen farewell to a remarkable performer. By the time he filmed George Sluizer’s Dark Blood several months later, he was reportedly off drugs – that fateful night at the Viper Rooms in Los Angeles being an aberration – and back to his best. One can only pray that the film, which premiered in Holland last week to raves from critics, will at last afford River Phoenix a fitting swansong.