1. Heath Ledger, The Dark Knight (2008)
As an intellectual exercise, try to think of how Heath Ledger’s galvanizing performance as the Joker in The Dark Knight might have been perceived had he not died half a year before its release. Would it seem as eerie and disturbing? Would he have collected Supporting Actor awards from every guild, academy, and critics’ group from the redwood forest to the Gulf Stream waters? Maybe. But it’s ultimately futile to try to separate the two, because Ledger’s Joker isn’t just a testament to his immense talent and commitment to craft, but a chilling depiction of anarchy and nihilism in its purest form. Here’s a character who wishes for nothing but to coax the world deeper into chaos and darkness, played by an actor who lost himself to a cocktail of prescription pills meant to relieve his own anxiety, depression, and pain. The two aren’t to be confused by any means, but Ledger transformed the Joker into the ultimate modern boogeyman, and his passing lingers strongly over the movie.
2. Peter Finch, Network (1976)
Though several actors have been posthumously nominated for Oscars, only one person before Heath Ledger actually took the award from beyond the grave: Australian actor Peter Finch, who won for his iconic final role as crazed network-news-anchor-turned-prophet-of-doom Howard Beale in 1976’s Network. Finch enjoyed a long, critically lauded acting career, but Howard Beale is easily his most memorable role, and as final roles go, it’s a doozy. Still, it’s surprising to realize just how little screen time he actually gets in the movie. Paddy Chayevsky’s script mainly follows protagonist William Holden, and largely confines Howard’s presence to four carefully crafted scenes in which he evolves from a suicidal wreck to an insane ranter who plans to change the world through his power as the mystic voice of television. Finch makes every moment count, though, and the entire movie would have been a disaster if he hadn’t nailed the performance. The role could have gone off the rails into hammy overacting, but with subtle nuance and wild extravagance, Finch perfectly captures the dual aspects of Beale: He’s totally, completely bonkers… and he’s right.
3. John Kennedy Toole, A Confederacy Of Dunces (written 1968 and before, published 1980)
One of the great comic novels of the 20th century, A Confederacy Of Dunces was published in 1980 and won the Pulitzer Prize in 1981. By that point, its author had been dead 12 years. A meaningful romp through a New Orleans populated with colorful characters, the book gained a cult following that has only grown over the years. It began with Toole’s mother, who worked tirelessly to get her son’s unpublished masterpiece into print, a cause taken up by Walker Percy, who recognized it as a different sort of Southern classic than his own work. Only Toole’s suicide, said to be spurred in part by his novel’s rejection, casts a pall over its enduring success.
4-5. Franz Kafka, The Trial and The Castle (written 1920 & 1922; published 1925 & 1926)
In a sense, almost everything we have from Franz Kafka is a posthumous project. Constantly dubious of his own ability as a writer and armed with a highly unusual style, he sold only a few short stories in his lifetime, and no novels. Prior to his death, he handed all his finished and unfinished manuscripts to his friend Max Brod, with the instruction that they all be burned unread. Fortunately for Western literature, Brod had a higher estimation of Kafka’s literary talents than Kafka did, and in the years after the author’s death, Brod struggled mightily to get them into print. The results included The Trial, perhaps Kafka’s best-known work, which turned his name into an adjective with its depiction of a hapless individual struggling against a paralyzing bureaucracy, and The Castle, a surrealist masterpiece of alienation and frustrated intentions. Both made it to print two years after Kafka’s death, and some have speculated that he chose Brod as his executor because he knew Brod wouldn’t obey his wishes. It’s unimaginable to think of these brilliant books ending up as ash in a fireplace.
6. Jeff Buckley, Sketches (for My Sweetheart The Drunk) (1998)
“The songs that would have been My Sweetheart The Drunk are the true ‘remains’ of Jeff Buckley, not the speck of dust that was pulled out of the Wolf River.” So writes Buckley’s mother, Mary, on the album’s liner notes, but in truth, the final album was unsettled on the summer night the gifted singer-songwriter went for a dip in a Memphis river and drowned. The first disc was intended as his eagerly anticipated follow-up to 1996’s breakthrough Grace, with production by Television’s Tom Verlaine, but Buckley wasn’t happy with the result, and he staked out in Memphis to try again with Grace producer Andrew Wallace. Based on the 10 gorgeous, haunting, sonically varied tracks that would have constituted the Verlaine version—the second disc is mostly odds and ends—it’s hard to figure out what put Buckley off so much, other than a perfectionist streak. And anyone looking for a metaphor for Buckley’s short, passionate career will find it in “Vancouver,” a track that builds and builds, growing ever more dramatic, until stopping short on an abrupt crescendo.
7-8. James Dean, Rebel Without A Cause and Giant (1955/1956)
A month before the release of Rebel Without A Cause, its star, James Dean, crashed his Porsche 550 Spyder into another car on a California highway. Thus ended one of the most promising acting careers of the ’50s. The troubled teen Dean played in Rebel—always courting danger and death—took on an added dimension with the audiences of 1955, who helped make the actor into an icon. They also flocked to see Dean’s final completed role in Giant, a sweeping tale of Texas ranch life in which Dean played a handyman with a grudge against his rich boss, Rock Hudson. On a subtextual level, Giant is all about Dean’s mumbly Method acting and unpredictable gesturing, and how it provides a clear, appealing alternative to Hudson and Liz Taylor’s staid Hollywood classicism. Dean turned Giant into a story about the new world of cinema and theater he was helping usher in, even if he had to sacrifice himself to do it.
9. Stanley Kubrick, Eyes Wide Shut (1999)
The first question: Had Stanley Kubrick lived to see the release of Eyes Wide Shut, how would he have felt about the digital figures inserted into the orgy sequence to keep the film from getting an NC-17 rating? Perhaps the MPAA would have prevailed in the end, but there’s little doubt that the reclusive director would have pounded them with angry faxes first. Death at least saved him from the inanities of the film’s release in the middle of summer-blockbuster season (between Wild Wild West, American Pie, and The Haunting remake) and its chilly critical reception, which has predictably thawed out in the decade since. Now, Eyes Wide Shut can be appreciated as a fitting swan song, a dreamlike meditation on the bonds of marital fidelity that wasn’t made for its time, but for all time, just like every other entry in Kubrick’s extraordinary filmography.
10-11. Elliott Smith, From A Basement On The Hill (2004) and New Moon (2007)
Controversy dogged the release of Elliott Smith’s final studio album, which he was in the midst of recording when he died in 2003. Final mixes were handled by Smith’s longtime producer Rob Schnapf and Smith’s former flame, Joanna Bolme; they apparently had a ton of material to work with (Smith supposedly wanted to release a 30-track double album), and they did an admirable job of completing his vision. Still, From A Basement On The Hill was a remarkably tough listen both because of its subject matter (“I know how I'll begin and how I'll end / strung out again”) and the proximity to his death. The double-disc collection New Moon, released in 2007, is even better, collecting a variety of tracks from Smith’s most furiously prolific period, between 1994 and 1997.
12. Ian Curtis, Closer (1980)
Ian Curtis hanged himself on May 18, 1980, two months to the day before his band, Joy Division, released its intensely anticipated second album. The whole scenario couldn’t be any more perfectly goth —look at the cover, for starters—but of course Joy Division never really fit that tag anyway. Curtis left behind an untarnished musical legacy: Closer and Unknown Pleasures make an incredible pair, with the former hinting hardcore at the despair Curtis was going through in his personal life. “Mother I’ve tried, please believe me / I’m doing the best that I can / I’m ashamed of the things I’ve been put through / I’m ashamed of the person I am,” he sings. And so on.
13. Tupac Shakur, Gridlock’d (1997)
Tupac Shakur was arguably as gifted an actor as he was a rapper, though he got precious few opportunities to display the depth and breadth of his talents. Shakur was mostly cast in gangsta, badass roles that jibed with his self-styled outlaw image—some transcendent and unforgettable, like the iconic thug Bishop in Juice, and others campy and ridiculous, like 1996’s Bullet, which cast him as a perpetually shouting kingpin opposite Mickey Rourke. A joyous exception can be found in 1997’s posthumously released Gridlock’d, a sadly overlooked black comedy that showcased Shakur’s vulnerability, sadness, and comic chops. (Far more talent than whatever’s evidenced in the mass of 2Pac musical flotsam that came out after his death.) Shakur more than held his own opposite Tim Roth as a junkie battling an army of red tape and bureaucratic bullshit as he struggles to get clean, avoid crime-word enemies, and check into rehab.
14. Johnny Cash, American V: A Hundred Highways (2006)
Johnny Cash sounds so weak and frail throughout 2006’s A Hundred Highways,the fifth entry in his seminal American Recordings series, that listening to it can be painful. The quiver in Cash’s once-booming voice adds an additional element of poignancy to songs like “I’m Free From The Chain Gang Now,” the album’s bittersweet closer and the perfect way to end a legendary career.
15-16. Bill Hicks, Arizona Bay and Rant In E-Minor (1997)
Bill Hicks had already put out two comedy albums before his 1994 death from pancreatic cancer, but while 1990’s Dangerous and 1992’s Relentless are undeniably solid, Hicks might have been relegated to footnote status in the annals of stand-up history if not for the release of Arizona Bay and Rant In E-Minor three years after he died. Arizona Bay is Hicks at his most polished, hitting his usual satirical targets of religion and government as well as dissecting the Rodney King verdict, the riots that followed, and his own obsession with videogames and porn. It’s a tour de force of surface-level hilarity combined with surprising depth; the guitar noodlings (done by Hicks himself) filling the spaces between routines are dispensable, but it’s easy to hit the skip button once the music starts up. Then there’s Rant In E-Minor and its 36 tracks of rage and bile rolled up in punchlines and “purple-veined dick jokes.” While Rant is a little ragged around the edges, the end result is the funny, painfully honest expression of a man who was nearly always just a little too smart for the room.
17. Joe Orton, What The Butler Saw (1968)
There’s nothing particularly tragic about What The Butler Saw, a sort of ground-zero type sex farce that stretches the conventions of the genre to their absurdist conclusions. That’s probably how Joe Orton would’ve wanted it. Bludgeoned to death by his lover in 1967, Orton died with only a handful of productions under his belt, having already made a name for himself as a brilliant, darkly comic playwright; his most famous work at the time, Loot, detailed the adventures of a pair of thieves trying to hide stolen money in a dead woman’s coffin. Orton dealt with all sorts of weighty subjects, mocking convention and social mores, but the single most important element in his writing was the tone, an irreverence with which he greeted even the most serious theme. A cynicism without malice infects the entirety of Butler, in which a psychiatrist and his wife exploit their respective positions to attempt various seductions, with increasingly convoluted results. It’s the effort of a writer who’s just settled into his own voice; it’s just too bad that he never got the chance to say more.
18. Flann O’Brien, The Third Policeman (written 1940; published 1967)
Flann O’Brien was, for many years, the most underrated Irish novelist of the 20th century. His books, alternately philosophical and ribald, were amazingly well-written, but also incredibly funny, yet they had the bad luck to come out of Ireland at a time when George Bernard Shaw, Samuel Beckett, and James Joyce were also writing. O’Brien never reached their level of fame or praise in life, and he had so much trouble selling his last novel—the surreal, darkly comic The Third Policeman—that he eventually grew ashamed of it and started telling friends that the manuscript had been lost. Fortunately, it wasn’t, and when it was finally published a few years after O’Brien’s death, the world got a chance to see what it had been missing all this time: a bizarre murder mystery featuring one-legged bandits, a mysterious scientist, policemen who are part-bicycle, and a soul named Joe. It’s one of his best books, and received its biggest boost some 65 years after it was written when it turned up in an episode of Lost.
19. Bruce Lee, Enter The Dragon (1973)
The first martial-arts movie to come from a major U.S. studio, Enter The Dragon was Bruce Lee’s open love letter to his Chinese heritage, as well as a direct challenge to America, which had previously given him small, unsatisfying film roles, or kitschy sidekick TV roles. Lee co-produced the film, and was heavily involved in scripting its iconic, influential story about a martial artist trying to regain his school’s honor at a deadly tournament. He also choreographed and staged its frequent exciting fights. He spent his short career trying to break into Hollywood pictures—and then becoming a Hong Kong action superstar after Hollywood let him down—and the fact that Enter The Dragon made him a household name and started a massive kung-fu film boom in America (it’s a thrilling action film, in spite of its goofy overdubbed dialogue and sound effects) would presumably have been a major triumph for him had he lived to see its première. Instead, he died of mysterious, disputed causes at age 32, just weeks before the film’s American opening.
20. Charles Dickens, The Mystery Of Edwin Drood (written 1870; published 1871)
Charles Dickens got paid by the word, which is why so many of his works seem flatulent. But though Boz’s final novel was likewise a serial work, and a murder mystery at that, it’s actually terse by his normal standards. The book’s pervasive air of decadence and dread and its keenly described sense of place likewise make it appealing to even non-fans of Dickens’ work. Dickens died at age 58 before he could tell anyone whodunit, but that hasn’t stopped dozens of adaptations of the story from being made. There are radio adaptations, movie versions, TV miniseries, and even sequels, most of which take the standard interpretation that the death of scrappy young orphan Edwin Drood was at the hands of his dope-fiend uncle (and romantic rival) John Jasper. (Another mystery, the identity of enigmatic lodger Dick Datchery, is less certain.) A few have taken divergent paths, and there was even a widely publicized “trial” of John Jasper in 1914, presided over by “Judge” George Bernard Shaw.
21. Mitch Hedberg, Do You Believe In Gosh? (2008)
Almost every single Mitch Hedberg fan has a favorite among his harebrained one-liners about mundane topics, delivered deadpan like the great Steven Wright before him. The man wrote a lot, so it was hard to come to any consensus as to which gag was the best. (Though here’s one vote for “No matter how good I get at tennis, I’ll never be as good as a wall. The wall is fuckin’ relentless.”) Everyone agrees, though, that the comedian’s life was far too short; Hedberg died in 2005 due to a drug overdose at age 37. Last year, thanks to the work of his widow Lynn Shawcroft and Comedy Central Records, another Hedberg album surfaced: Do You Believe In Gosh?, cobbled together from unreleased recordings of old shows. The material is a fitting tribute to the comic’s ramshackle delight: Some bits humorously misfire, others involve playful audience banter, and the rest are pure, unfiltered Hedberg. No one else could make the line “I got a vest. If I had my arms cut off, it would be a jacket…” so damn entertaining.
22-23. Jane Austen, Northanger Abbey and Persuasion (written in 1803 & 1817; published in 1818)
Of Jane Austen’s scant six novels, only four were published in her lifetime. Northanger Abbey actually predates any of her published work, and was sold to a publisher who announced it on his list but never put it into print. (Instead, he sold the rights back to Jane’s brother Henry, unaware that the manuscript’s author was by that time a popular success.) On the other end of Austen’s productive life is Persuasion, her last completed novel. When her literary heirs published the two posthumously, the edition contained both books bound together—appropriate, since both feature the British resort of Bath as a major setting. Persuasion tells the story of a middle daughter, taken for granted by her histrionic family, who has a second chance at happiness with the naval officer whose suit she’d been persuaded to reject when she was younger. Its love story is one of the most quietly desperate and emotionally affecting of all Austen’s work. By contrast, Northanger Abbey is a sprightly satire on the very idea of the novel, featuring a protagonist whose romantic view of the titular estate comes from her steady diet of gothic fiction. In no way are these two novels lesser works, in spite of their posthumous publication. Proud Austenites who read all six books regularly—and consider them the only printed matter truly worthy of the appellation “novel”—certainly don’t discriminate against them.
24. Niccolò Machiavelli, The Prince (written 1513, published 1532)
Born into the political instability of 15th-century Florence, Niccolò Machiavelli watched as his city shrugged off the powerful Medici family to restore a republic backed by strongman Cesare Borgia. Machiavelli put his thoughts on how an effective ruler may best lay down the law in 1513, the same year a resurgent Medici force had him arrested, tortured, and sent into exile. Machiavelli’s name has become synonymous with cruelty and deception, but The Prince ultimately reads as a no-nonsense guide on imposing order on chaos, even if it means inspiring some fear along the way. Still, Machiavelli kept his advice to himself until after his death, when The Prince saw publication and his name took on infamy for his attempt to tell the truth about how those who pull the strings decide which strings to pull.
25. Joe Strummer, Streetcore (2003)
After a long stretch in the wilderness following The Clash’s demise, Joe Strummer spent his last few years on Earth making sense of his life’s work by putting the populism back in pop music, and the rock back in punk rock. Streetcore—the third album Strummer recorded with the eclectic beat merchants The Mescaleros—consists of whatever takes and mixes were completed before Strummer's death, and in a way, the record’s tinny sound and half-finished feel makes it seem more touching and direct than the final result might otherwise have been. Streetcore has a notebook-like quality: It’s packed with Strummer's first impressions on how to keep blurring the lines between “underclass” pop from around the world. At several points on Streetcore, Strummer growls out the words “This is London calling,” partly as a nod to The Clash’s legacy, and partly as an nod to the global community from one man who’d spent his life staying keenly attuned to what was beaming into his stereo.
26-plus. Emily Dickinson, almost everything
Emily Dickinson had a few verses published, usually in altered form, during her lifetime. But her legacy rests on the more than 800 poems she left behind in a collection of 40 hardbound books on which her legacy rests. Dickinson led an ever-increasingly reclusive existence inside her parents’ home, but a vivid life on the page. She drew on her love of literature to bend words and imagery into shapes never previously imagined. Though she was a faithful correspondent, the bulk of her writing seems to have been directed only toward herself. Dickinson instructed her sister to burn her papers upon her death. Like Max Brod, her sister disobeyed, and Dickinson’s reputation has grown ever since the first collection of her poems saw print in 1890, four years after death.
27-plus. Buddy Holly, various singles
February 3, 1959 was the day the music died, sort of. Buddy Holly went down alongside Richie Valens and the Big Bopper, but he kept releasing singles for another 10 years, including some of his best-known (and some of his best) songs. “Peggy Sue Got Married,” “True Love Ways,” “Crying, Waiting, Hoping,” and “Learnin’ The Game” all rolled out in the first years after Holly’s death, giving him the chart comeback he was trying to craft for himself before his untimely death. Holly left a lot behind, and in the rush to profit… err, pay tribute to his legacy, a lot of it got reworked in ways he might not have imagined. Is the real “Peggy Sue Got Married” the version with the cheesy background vocals, the one that sounds like a throwback to Holly’s erstwhile Crickets, or the home recording Holly certainly would have considered unfinished? One of the perils of dying young is that sometimes you’re kept working against your will.