The most tantalizing "What Ifs" in Hollywood history
Warner Bros.

The most tantalizing "What Ifs" in Hollywood history

Making movies is a fickle business. People dream big. They imagine grand epics with the biggest stars, and they believe deep in their hearts that their vision will payoff in boffo box office or a multitude of Academy Awards. Occasionally these risks pay off. More often than not, they crash and burn. Life gets in the way. Studio leadership changes, directors and writers fall out, people die unexpectedly... there are no guarantees. But this doesn't stop us from considering what could've been. In that spirit, here are fifty tantalizing woulda-coulda-shouldas. What if...

 
1 of 50

Sidney Lumet directed "Scarface" and Brian De Palma directed "Prince of the City"?

Sidney Lumet directed "Scarface" and Brian De Palma directed "Prince of the City"?
Universal

If all had gone according to plan in the early 1980s, Brian De Palma and playwright David Rabe would’ve adapted Robert Daley’s sprawling account of police corruption in New York City, while Sidney Lumet would’ve remade Howard Hawks’ classic gangster yarn with Al Pacino. De Palma wanted frequent collaborator Robert De Niro for his lead (which would’ve knocked the method legend out of Ulu Grosbard’s “True Confessions”), while Lumet viewed “Scarface” as a politically charged procedural about the exploding cocaine trade in America. Creative differences aligned for an ideal outcome. Producer Martin Bregman got the pulpy “Scarface” he wanted, and Lumet returned to a theme he’d mined brilliantly in “Serpico” (though he wanted a non-star for the lead, which landed him Treat Williams). De Palma, meanwhile, ported the suspenseful arcing-wire bit he’d concocted for “Prince of the City” over to his masterpiece “Blow Out”.

 
2 of 50

Steven Spielberg directed "Cape Fear" and Martin Scorsese directed "Schindler's List"?

Steven Spielberg directed "Cape Fear" and Martin Scorsese directed "Schindler's List"?
Universal

Universal Pictures acquired the rights to Thomas Keneally’s historical novel “Schindler’s Ark” in 1982, the very year the filmmaker cemented his status as Hollywood’s king of escapist entertainments via “E.T.: The Extra-Terrestrial” and “Poltergeist”. Spielberg, believing he wasn’t prepared to handle the difficult subject matter, spent most of the next decade offering the project to the more mature likes of Sydney Pollack, Roman Polanski, Brian De Palma, and Martin Scorsese. Scorsese accepted in the early ‘90s, but Spielberg suddenly had a change of heart. Spielberg compensated Scorsese with the remake of “Cape Fear”, which became the latter’s biggest box office hit up to that point; the former won his first Oscars for Best Picture and Director. That’s a fairly decent outcome.

 
3 of 50

Doris Day and Ronald Reagan played the Robinsons in "The Graduate"?

Doris Day and Ronald Reagan played the Robinsons in "The Graduate"?
20th Century Fox

This film is a bevy of “what ifs”, particularly when it comes to the casting of Mrs. Robinson. Jeanne Moreau, Patricia Neal, and several others were considered for Mrs. Robinson before Mike Nichols went with Anne Bancroft, but the most intriguing possibility involved the mischievous pairing of Doris Day with Ronald Reagan. America’s Sweetheart and one of the most loathed conservatives in Hollywood as the exemplars of parental hypocrisy at the height of the ‘60s protest movement. Day refused due to the film’s sexual content, but it’s the notion of Reagan as an emasculated authority figure that fires the imagination. His political ambitions could’ve been shot through the heart. Then he would’ve been free for the Murray Hamilton role he was born to play: the cowardly, commerce-driven mayor in “Jaws”.

 
4 of 50

Tom Cruise played Iron Man?

Tom Cruise played Iron Man?
Marvel

In 1998, the same year “Blade” sparked renewed interest in the cinematic potential of Marvel Comics’ massive catalog, Tom Cruise and producer Paula Wagner began developing “Iron Man” as a franchise character for the Hollywood superstar. The attraction is obvious. Ultra-charismatic industrialist who finds a moral backbone but can’t shake his hereditary alcoholism… lots for Cruise to chew on back when he liked to chew. Cruise’s involvement gave the second-tier character a high profile at the studios, but the finished product would’ve been a hybrid Iron Man powered by grounded, real-world tech. He moved on, and Marvel, in taking an unthinkable risk on recovering addict Robert Downey Jr., became the biggest show in town.

 
5 of 50

James Cameron made "Spider-Man"?

James Cameron made "Spider-Man"?
Columbia

James Cameron directing Leonardo DiCaprio as Peter Parker/Spider-Man pre-Titanic? It could’ve happened. Carolco acquired the rights for a Spidey flick from Menahem Golan’s cash-strapped 21st Century Film Corporation, and hired Cameron, smarting from the commercial failure of “The Abyss”, to bring the iconic superhero to big-screen life. By the time Cameron submitted his finely detailed “scriptment” in 1993, he’d repaired his reputation and then some thanks to “Terminator 2: Judgment Day”. Golan sued, and this, in tandem with Marvel’s decades-long rights issues, was enough to chase Cameron off the project. But had Cameron teamed with DiCaprio on “Spider-Man” instead of “Titanic”? That’s a butterfly effect with infinite possibilities.

 
6 of 50

Brad Pitt gave Harvey Weinstein a "Missouri whooping"?

Brad Pitt gave Harvey Weinstein a "Missouri whooping"?
20th Century Fox

Decades before movie mogul Harvey Weinstein was convicted and jailed for sexual assault, he nearly caught a beating at the hands of Brad Pitt. In 1995, when Pitt learned that Weinstein had made unwanted advances toward his then-girlfriend Gwyneth Paltrow, he pinned the executive up against a wall and warned him that a “Missouri whooping” was in his future if he ever did it again. Had Pitt delivered on that promise, one wonders how the press would’ve reacted to the next Robert Redford beating the tar out of a widely hated power player. Weinstein’s media machine likely would’ve gone into overdrive smearing Pitt as an out-of-control hothead with substance abuse issues (or something to that untrue effect), but the rising star’s image was spotless at the time. Weinstein was a year away from “The English Patient” winning Best Picture. This could’ve ruined him.

 
7 of 50

Martin Brest hadn't been fired from "WarGames"?

Martin Brest hadn't been fired from "WarGames"?
MGM

This seems like small potatoes until you realize Martin Brest skipped directly from one of 1983’s biggest hits to 1984’s biggest hit. The implications are huge. The film’s massive success kicked Eddie Murphy’s career into overdrive, giving the star his first bona fide franchise. It also established Brest as a master of action comedies, which gave us the gift of “Midnight Run” four years later. Had “Beverly Hills Cop” been made with a less ambitious director, the flimsiness of the screenplay might’ve been more apparent, rendering this a run-of-the-mill ‘80s actioner elevated by Murphy’s ad-libbing genius.

 
8 of 50

The shark worked?

The shark worked?
Universal

“Jaws” was a notoriously difficult production for twenty-six-year-old Steven Spielberg. He shot the film on open water, which subjected the crew to the unpredictable whims of mother nature. The mechanical sharks proved especially vulnerable to the harsh shooting environments; their constant malfunctioning forced Spielberg to shoot around them for a longer duration of the shoot. This sparing use of the beasts ramped up the suspense in the film’s first two acts, turning the shark fin, in tandem with John Williams’s “duh-dun” theme, into an iconic symbol of terror. Had the mechanical sharks worked early on, this could’ve been a very different, less successful film. This means no “Close Encounters of the Third Kind”, which definitely means no “1941” and so on.

 
9 of 50

Eddie Murphy co-starred in "Star Trek IV"?

Eddie Murphy co-starred in "Star Trek IV"?
Paramount

There have been lots of high-profile Trekkers in the Hollywood ranks (e.g. Tom Hanks, Ben Stiller, and Elvis Presley), but the stars have rarely aligned for one of them to join Starfleet’s ranks. Not so for Eddie Murphy, who, as Paramount’s top contract star, had an opportunity to co-star in the studio’s “Star Trek IV: The Voyage Home”. Murphy would’ve played a present-day Berkeley astrophysicist who teams up with the time-traveling Enterprise crew. This is the role that eventually morphed into Catherine Hicks’s whale researcher. The combination of Murphy and “Star Trek” could’ve resulted in a broadening of the latter’s niche-ish appeal, encouraging Paramount to kick more money into the franchise going forward. Perhaps we’d be spared William Shatner’s “Star Trek V: The Final Frontier”. We’ll never know.

 
10 of 50

Universal made Guillermo del Toro's "At the Mountains of Madness"?

Universal made Guillermo del Toro's "At the Mountains of Madness"?
Lionsgate

In 2010, it appeared the Academy Award-winning filmmaker of “Pan’s Labyrinth”, “Pacific Rim” and “The Shape of Water” had, at last, dragged his Lovecraftian labor of love to the development finish line. His chilling, R-rated tale of monstrous findings in Antarctica had a major movie star in Tom Cruise and a world-class producer in James Cameron. Then Universal experienced a rough year at the box office and pulled the plug on the mega-budget horror flick. Had the film been made to del Toro’s specifications, it would’ve been a boon for smart, large-scale adult horror movies. Could it still happen? You’ve spent a lot more money on much more dubious projects, Netflix. Let right be done.

 
11 of 50

Guillermo del Toro directed "The Hobbit"?

Guillermo del Toro directed "The Hobbit"?
Warner Bros

Given how Peter Jackson’s trilogy turned out, it’s tempting to say this would’ve been a waste of del Toro’s time and talent. But del Toro’s vision of a two-part tale made a great deal of sense, and also offered him a good deal of creative leeway. The first installment would’ve been “The Hobbit”, a slender novel that contains enough incident for one movie. The second chapter was to provide connective tissue between the narratives of “The Hobbit” and “The Lord of the Rings”. This would’ve allowed del Toro to create all kinds of new monsters for Jackson’s version of Middle Earth. That alone would’ve been worth the price of admission. But everything worked out pretty well for del Toro in the long run.

 
12 of 50

Warner Bros. powered through Tim Burton's "Superman Lives"?

Warner Bros. powered through Tim Burton's "Superman Lives"?
Warner Bros

Tim Burton spent a year of his life (and $30 million-plus of Warner Bros’ money) developing a massive reboot of the Superman franchise that was set to star Nicolas Cage as the Man of Steel, Chris Rock as Jimmy Olsen, Michael Keaton in an unspecified role and… someone big as Lois Lane (Sandra Bullock, Julianne Moore, and Courtney Cox were reportedly in the running). Sets were built. Cage did a costume fitting. It was going to happen. And with out-of-control producer Jon Peters meddling in just about every aspect of production, it was shaping up to be an epic disaster (in which Superman battles a giant spider at the end). The damage to the Superman brand and Burton’s career would’ve been considerable. “Sleepy Hollow” never happens, and Fox probably looks to another director for a “Planet of the Apes” reboot. Meanwhile, WB likely thinks twice about blowing $200 million on Bryan Singer’s “Superman Returns”.

 
13 of 50

Warner Bros. let Richard Pryor star in "Blazing Saddles"?

Warner Bros. let Richard Pryor star in "Blazing Saddles"?
Columbia

Mel Brooks initially tabbed the genius comedian to star as Bart, the new black sheriff of the very white Rock Ridge. The studio objected to the edgy stand-up, causing Brooks to go with the decidedly more urbane Clevon Little. With Pryor in the lead, the tone of the movie would’ve been much sharper and probably more confrontational. Pryor’s ad-libbing expertise likely would’ve come into play as well. He was such an explosive talent, he could’ve easily dominated the movie. Pryor made a huge impact as a co-writer (according to Brooks, he loved writing for Mongo), but we’d be talking about, and almost certainly loving, a very different “Blazing Saddles” today had WB not gotten cold feet.

 
14 of 50

Universal hadn't shut down "Jaws 3, People 0"?

Universal hadn't shut down "Jaws 3, People 0"?
Universal

Yes, Universal came very close to mashing up two of their most prized properties, Jaws and National Lampoon, for a showbiz spoof that would’ve sent up the then-nascent franchise craze. Joe Dante, fresh off “Piranha”, was set to direct, while the up-and-coming writing duo of Tod Carroll and John Hughes was hired to write the script. Rushed through development (they were already building sets and had a completed shark), the screenplay has half of a good idea and an unfavorable laugh-to-groan ratio. It would’ve tanked. Dante probably gets “The Howling” made, but would Steven Spielberg be open to hiring Dante for “Gremlins”? Probably not. As for Hughes, he survived the dreadful “National Lampoon’s Class Reunion” in 1982, but this would’ve been a high-profile bomb. Would Universal stick with a screenwriter who had a hand in killing the “Jaws” franchise? Ask Joe Alves, who never directed another movie after “Jaws 3D”.

 
15 of 50

Dennis Hopper hadn't pulled a knife on Rip Torn?

Dennis Hopper hadn't pulled a knife on Rip Torn?
Sony Classics

When Dennis Hopper was pulling his New Hollywood opus “Easy Rider” together, the film’s screenwriter, Terry Southern, came up with the notion that Rip Torn would be perfect as jailbird lawyer George Hanson. A dinner meeting that ended with the volatile Hopper pulling a knife on the volatile Torn, who used his expertise as a former Military Policeman to disarm the New Hollywood auteur, put the kibosh on that. Jack Nicholson was cast, and his iconic performance launched him to stardom. Put Torn in that role, and the magnetically surly actor could’ve easily had a ‘70s run to rival Nicholsons.

 
16 of 50

David Puttnam weren't a vindictive jerk?

David Puttnam weren't a vindictive jerk?
Columbia

When David Puttnam was named Columbia Pictures’ head of production in 1986, he inherited Elaine May’s pricey desert comedy, “Ishtar”. Puttnam hated stars, Dustin Hoffman and Warren Beatty, considering them the poster children for ego-driven production overruns at Hollywood studios. As the release date neared, Beatty and others (including May’s longtime comedy partner Mike Nichols) believed Puttnam was responsible for leaking toxic buzz to the press in order to torpedo the film’s box office. Puttnam won the battle, while May, a brilliant filmmaker, lost the war. She never made another movie. Who knows what treasures we missed out on?

 
17 of 50

Sean Connery starred in "On Her Majesty's Secret Service"?

Sean Connery starred in "On Her Majesty's Secret Service"?
MGM

It’s the best James Bond film with the weakest James Bond. Sean Connery bolted the franchise after 1967’s “You Only Live Twice”, leaving producer Albert “Cubby” Broccoli to replace him with model George Lazenby. Lazenby looked the part, but, in his first feature role, lacked his predecessor’s suave certitude. It’s still an excellent movie (with the greatest Bond girl ever in Diana Rigg), but it would’ve been Connery’s crowning achievement in the role that made him a global superstar. At a bare minimum, we probably don’t get the lousy “Diamonds Are Forever” - or if we do, it’s with Lazenby, which gives Roger Moore a chance to pull the series out of the doldrums with “Live and Let Die”.

 
18 of 50

George Miller's "Justice League"?

George Miller's "Justice League"?
Warner Bros

Warner Bros' aimless development of its DC superhero properties is a wasteland of “what ifs”, but George Miller’s “Justice League: Mortal” would’ve at least been a glorious disaster. The “Mad Max” director auditioned dozens of young stars, winding up with Armie Hammer as Batman, D.J. Cotrona as Superman, Megan Gale as Wonder Woman, Adam Brody as The Flash, Common as John Stewart/Green Lantern, and Jay Baruchel as Maxwell Lord. The project, considered separate from Christopher Nolan’s Batman series, was speeding toward principal photography with a reported budget of $220 million until the WGA strike of 2007 put everything on hold. When “The Dark Knight” exploded at the box office in ‘08, WB killed the production. The film could’ve caused confusion amongst mainstream moviegoers and kneecapped the Superman franchise for the third time in a decade. Martin Campbell’s “Green Lantern” surely would’ve been scuttled. Nolan’s movies would’ve been fine, but WB would’ve found themselves… about where they are right now with their DC characters.

 
19 of 50

George A. Romero made his epic version of "Day of the Dead"?

George A. Romero made his epic version of "Day of the Dead"?
Laurel

How does the “Gone with the Wind of zombie films” sound? Filmmaker George A. Romero was referring strictly to the scope of his follow-up to “Dawn of the Dead” (though we’d love to see Scarlett O’Hara mooning over an undead Ashley Wilkes), which would’ve concluded with a zombie war. Alas, no distributor was about to release an unrated anything into theaters at the budget Romero requested, so he made the massively scaled-back “Day of the Dead” instead. But what if, say, maverick producers like Golan-Globus had ponied up $10 million for Romero’s gory, MPAA-flouting vision, and it had been a critically acclaimed hit like his last two zombie movies? This might’ve emboldened other producers to fire up double rockets at the ratings board and take risks on movies that offended the sensibilities of those killjoy prudes.

 
20 of 50

Stanley Kubrick made "Napoleon" with Jack Nicholson?

Stanley Kubrick made "Napoleon" with Jack Nicholson?
Warner Bros

Stanley Kubrick’s longtime fascination with the life of Napoleon Bonaparte nearly culminated in what would’ve been the most epic Hollywood production since “Gone with the Wind”. After the mindblowing achievement of “2001: A Space Odyssey”, MGM was prepared to let the meticulous auteur plow forward with a sweeping biopic that would’ve required the hiring of over 40,000 extras for the battle sequences alone. It was a mad gamble, even with newly minted star Jack Nicholson in the lead. After the failure of Sergei Bondarchuk’s “Waterloo” in 1970, MGM pulled out. Had they gone all in, “A Clockwork Orange” and “Barry Lyndon” get punted (the latter likely scratched altogether), while Nicholson doesn’t make “Five Easy Pieces” or “Carnal Knowledge”. For starters.

 
21 of 50

Jim Carrey played Captain Jack Sparrow?

Jim Carrey played Captain Jack Sparrow?
Disney

The role that turned Johnny Depp into the worldwide superstar he was always supposed to be nearly went to Jim Carrey as his star was on the wane. Mindful of his box office appeal, Carrey opted for “Bruce Almighty”, a lazy formula comedy that allowed the star to coast on his rubber-faced talents. Though Carrey is a wonderfully inventive performer, it’s easy to see how he might’ve treated Sparrow as a paycheck gig, as opposed to “Eternal Sunshine of the Spotless Mind”, which he made the following year. Depp needed the part more than Carrey, but, ironically, earned the Oscar nomination that Carrey has been chasing since “The Truman Show”. Long-term, Carrey would’ve been fine. Depp, however, might’ve never popped.

 
22 of 50

Leonardo DiCaprio chose Dirk Diggler over Jack Dawson?

Leonardo DiCaprio chose Dirk Diggler over Jack Dawson?
Paramount

Leonardo DiCaprio was always going to be one of the biggest movie stars on the planet. It was just a question of which movie rocketed him into the rarified air of Brad Pitt, Tom Cruise, and Will Smith. This was a no-lose proposition for DiCaprio, but his boyish star turn in “Titanic” did put him behind the matinee-idol eight ball for a time, while “Boogie Nights” would’ve forced him to play against his cocksure charm. Figuratively. “Boogie Nights” was never going to be “Titanic”, but was DiCaprio looking for a “Titanic” in the first place? Maybe he gets a Best Actor nomination for “Boogie Nights”, eschews Woody Allen’s “Celebrity” and finds a place in “Magnolia”. One thing’s for sure: he wouldn’t have been a big enough movie star to get Martin Scorsese’s “Gangs of New York” greenlit. So who does Scorsese cast instead? So much to ponder.

 
23 of 50

Pierce Brosnan became James Bond in 1987?

Pierce Brosnan became James Bond in 1987?
NBC

Another Bond “what if”, but is it possible that this almost worked out for the best? A decade-plus of Roger Moore as Ian Fleming’s 007 had turned the character into a campy quip machine. Moore was also pushing sixty, and it showed. Pierce Brosnan was playing a younger, snappier version of Moore’s Bond on NBC’s “Remington Steele”, and everyone just knew he’d be the next Bond. Cubby Broccoli agreed, and the offer was made. Alas, Brosnan couldn’t get out of his NBC contract, so Broccoli hired Timothy Dalton instead. Fleming fans are largely fond of Dalton’s unpolished portrayal; for two films, they got to see the ruthless Bond of the books. This whetted the appetite for Daniel Craig’s rough-and-tumble take on the character in 2006’s “Casino Royale”. Had Brosnan won the role in 1987, it would’ve been more of the glib same, cementing Bond as a caricature instead of a debonair killer.

 
24 of 50

CBS let Tom Selleck out of his contract for "Raiders of the Lost Ark"?

CBS let Tom Selleck out of his contract for "Raiders of the Lost Ark"?
CBS

Tom Selleck has nothing to complain about. “Magnum P.I.” was not only a long-running ratings hit for CBS, but it was also a critical darling that allowed the star to take risks as an actor, much like his mentor, James Garner did on “The Rockford Files”. Money-wise, Selleck did great. But would he have been as resourceful in the moment as Harrison Ford was in “Raiders of the Lost Ark”? Unless Selleck coincidentally contracted the same stomach flu as Ford, the fight with the sword-wielding assassin would’ve gone down as choreographed. This isn’t idle speculation. Selleck was Spielberg’s and Lucas’s first choice. Selleck would’ve been a heckuva movie star.

 
25 of 50

Jodorowsky's "Dune"?

Jodorowsky's "Dune"?
Sony Classics

If a visionary director was ever going to get away with making a fourteen-hour adaptation of a popular science fiction novel, the 1970s were definitely the decade in which to do it. If you watch the excellent documentary that details precisely what Alejandro Jodorowsky had in mind, you’ll likely come away thinking it would’ve been a disaster, while feeling thankful for his expansive, druggy design ideas that influenced the next wave of sci-fi movies like “Star Wars” and “Alien”. Had the film bombed, anyone carrying around its stink (including Dan O’Bannon, H.R. Giger, and Moebius) would’ve been persona non grata at the studios. Maybe “Alien” doesn’t happen. That would be a tremendous loss.

 
26 of 50

Robert Duvall and Winona Ryder had been in "The Godfather Part III"?

Robert Duvall and Winona Ryder had been in "The Godfather Part III"?
Paramount

These are two massive “what ifs” in the same movie with very different implications. The trilogy capper gets a bad rap, but even the film’s staunchest defenders must concede that the absence of Robert Duvall’s Tom Hagen diminished the film - especially because the whole world knew it was a contractual dispute that forced Coppola and Puzo to write the character out of the script. Michael’s tough treatment of his brother would’ve added an essential layer of tension that the movie lacked. And while Sophia Coppola did her best in an impossible situation, having an experienced actor like Ryder in the pivotal role of Michael’s daughter would’ve helped tremendously. There’s a masterpiece lurking in “The Godfather Part III”, but it’ll always feel compromised without Hagen. 

 
27 of 50

Ridley Scott made "I Am Legend" with Arnold Schwarzenegger?

Ridley Scott made "I Am Legend" with Arnold Schwarzenegger?
Getty Images

This project went through myriad incarnations before getting watered down for Will Smith. Mark Protosevich’s adaptation of Richard Matheson’s groundbreaking work of post-apocalyptic science fiction was a leap-off-the-page screenplay that would’ve altered the genre landscape at a time when mindless escapism dominated. Ridley Scott reworked Protosevich’s script with John Logan (“Gladiator”), opting for a dialogue-free first hour. With Schwarzenegger in the lead, the film possessed the potential to be the arty blockbuster “Blade Runner” should’ve been. After two years of box office disappointments, WB lost its nerve and pulled the plug. Schwarzenegger continued to play it safe, and then became the governor of California.

 
28 of 50

Will Smith hadn't passed on "Django Unchained"?

Will Smith hadn't passed on "Django Unchained"?
Getty Images

Will Smith didn’t get to where he is today by taking risks. His music was accessible to kids and their parents, while his film career is a study in coasting. He doesn’t like to be challenged, but when Quentin Tarantino came calling with “Django Unchained”, Big Will had to listen. Tarantino’s track record with actors was unimpeachable, and Smith wanted an Oscar. But the actor’s ego got in the way. He wanted to sand down the edges and foreground Django’s arc at the expense of the other characters’ screen time. While Jamie Foxx was terrific in the lead role, watching Smith give himself over to an auteur for once would’ve been thrilling. Maybe he’d like it enough to do it again!

 
29 of 50

George Lucas made "Apocalypse Now" during the Vietnam War?

George Lucas made "Apocalypse Now" during the Vietnam War?
Paramount

John Milius’s Vietnam-set riff on Joseph Conrad’s “Heart of Darkness” was initially written at the urging of George Lucas and Steven Spielberg in the late 1960s. A war nut stung by being declared unfit to serve in the army due to his asthma, Milius poured his combat fantasies and wacky colonialist notions into the script. Upon completion, he tapped Lucas to direct the film. The recent USC graduate envisioned Milius’s tale as a 16mm vérité partially shot in South Vietnam with real soldiers during the height of the war. The studio wanted no part of this, so the project was put into turnaround. Had Lucas somehow gotten away with this insane gamble, and survived the shoot, this would’ve been “Medium Cool” on steroids. The scathing experience might’ve altered his perspective on “Star Wars”, dampening its gee-whiz exuberance. Meanwhile, Coppola would’ve had to find another epic project on which to lose his mind.

 
30 of 50

Stanley Kubrick hadn't scared The Beatles off "The Lord of the Rings"?

Stanley Kubrick hadn't scared The Beatles off "The Lord of the Rings"?
Apple Films

Everyone was gaga for J.R.R. Tolkien’s “The Lord of the Rings” in the 1960s, including The Beatles. Dennis O’Dell, the head of Apple Films, turned the Fab Four on to the Middle Earth saga while they were studying with the Maharishi in India. They were excited by the synergistic potential of recording a double album to go along with the movie (in which they’d star as Hobbits) until they met with one of the project’s potential directors, Stanley Kubrick. Though he was developing his cast-of-thousands Napoleon biopic at the time, Kubrick cautioned the band that an adaptation of Tolkien’s epic was impossible. The Beatles moved on and, a few years later, broke up. Had they made the film, Led Zeppelin would’ve had to find a new shtick. More significantly, “The White Album” and “Abbey Road” either don’t happen or sound a lot different.

 
31 of 50

Anyone had made "A Confederacy of Dunces"?

Anyone had made "A Confederacy of Dunces"?
Lionsgate

John Kennedy Toole’s raucous New Orleans masterpiece, published posthumously in 1980, has stymied the likes of Buck Henry, Harold Ramis, Stephen Fry, and Steven Soderbergh. The novel’s outsized, indolent protagonist was, at various points, to be portrayed by John Belushi, John Candy, Chris Farley, and Will Ferrell. Everything from nervous studio execs to natural disasters has prevented the project from moving forward (Soderbergh believes the material is cursed), but a great adaptation (which doesn’t seem impossible) would be the ultimate Big Easy movie; it’d showcase the city in a way movies have only managed to do in passing. The last two decades have been rough on NOLA. It’s the most culturally rich city in the country. Americans need to have a stake in its welfare.

 
32 of 50

Anyone had made "Harrow Alley"?

Anyone had made "Harrow Alley"?
Columbia

The plight of Walter Newman’s screenplay, “Harrow Alley”, has been lamented for over forty years . The darkly comedic epic, set in 17th Century England during the Great Plague, first caught the eye of John Huston in 1963. Five years later, George C. Scott optioned the script, but he could never get the tale, which laughs irreverently in the face of death, before cameras (even with a young, stardom-bound Mel Gibson attached). Emma Thompson set up the project three years ago as a miniseries at HBO, but there’s been no reported movement since. It is widely considered to be the best-unproduced screenplay in Hollywood. Paired with the right director in the pre-CG era, it might’ve emboldened other studios to take risks on big, bleak material. Thompson is a wonderful filmmaker, and will hopefully bring it to life, but the best version of “Harrow Alley” feels like it’s in the rearview.

 
33 of 50

Jack Arnold remade "The Creature from the Black Lagoon"?

Jack Arnold remade "The Creature from the Black Lagoon"?
Universal

Universal is still trying to bring this classic monster back to life, and there are some intriguing screenplays out there (particularly Gary Ross’s), but the weirdest, most intriguing attempt was back in the early 1980s when John Landis hired Hammer horror legend Nigel Kneale to script a remake for the original film’s helmer, Jack Arnold, to direct. Landis and makeup f/x wizard Rick Baker took to Steven Spielberg’s swimming pool to shoot 3D camera tests with Playboy Playmate Gig Gandel. Universal honcho Sidney Sheinberg loved the footage so much that he greenlit “Jaws 3D” (in the cheapest stereoscopic process available). Had Sheinberg gone the other way, and this team hit paydirt, a resurgent monster movie craze might’ve saved horror from its slasher rut (which led to a desert period for the genre in the 1990s).

 
34 of 50

Peter Jackson made "King Kong" after The Frighteners"?

Peter Jackson made "King Kong" after The Frighteners"?
Universal

Peter Jackson’s first studio feature, “The Frighteners”, might’ve underperformed at the box office, but Universal was still high enough on the New Zealand filmmaker to proceed with his remake of “King Kong”. It was both a labor of love and a protective act for Jackson; “King Kong” is one of his favorite movies, and he couldn’t bear to see a lesser director churn out an impersonal redo. His original screenplay is a rollicking bit of high adventure. Set during World War I, it’s a paean to the first air aces, the silent film era, and Skull Island’s biggest, hairiest resident. It’s a brisk yarn that hits all the requisite emotional beats, the opposite of the heartfelt, yet terminally bloated film Jackson delivered post-”Lord of the Rings”. It’s highly unlikely another filmmaker would’ve swiped the Tolkien series from Jackson (he was already developing it with Miramax), but if he’d scratched the Kong itch prior to his Middle Earth sojourn, maybe he would’ve run a more interesting victory lap.

 
35 of 50

Steven Spielberg made "Night Skies"?

Steven Spielberg made "Night Skies"?
Columbia

There’d be no “E.T.: The Extra-Terrestrial”. “Night Skies” was apparently hatched as an insurance policy against Columbia sequelizing “Close Encounters of the Third Kind”. Written by John Sayles, it’s a siege tale about a trio of not-so-friendly aliens terrorizing a rural family. Rick Baker did creature f/x tests, and Spielberg hired Tobe Hooper to direct. The project was eventually stripped for parts. The friendly alien of the trio became E.T.; the besieged family became “Poltergeist”; and the bad alien, called “Scar”, became “Stripe” in “Gremlins”. One movie would’ve knocked all of those films out of commission.

 
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Steven Spielberg made "Crusing"?

Steven Spielberg made "Crusing"?
Warner Bros

Gerald Walker’s novel about a serial killer targeting gay men making New York City’s leather scene ultimately found its way to William Friedkin, who delivered a sensationalized snapshot of a thriving subculture. Friedkin was fearless. Spielberg was the protagonist of Andrew Gold’s “Lonely Boy” made flesh. How producer Philip D’Antoni landed on the latter to develop this project probably had everything to do with availability. Friedkin had just won an Oscar for Best Director, and was about to make “The Exorcist”. Spielberg was a hot, young talent coming off “Duel”, so why not? What a pre-”Jaws” Spielberg would’ve made out of this pitch-black material is anyone’s guess. It would’ve taken him out of the running for “The Sugarland Express”, and possibly strained his blossoming relationship with Universal.

 
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Steven Spielberg made "The Spy Who Loved Me"?

Steven Spielberg made "The Spy Who Loved Me"?
MGM

Like many Baby Boomers, Steven Spielberg was infatuated with Ian Fleming’s James Bond, and particularly enamored of the ‘60s cinematic run with Sean Connery. Depending on who’s telling the story, an eager Spielberg either approached the producers to make “The Spy Who Loved Me” his first post-”Jaws” project or the producers met with him while he was editing the killer shark flick and decided to go in a different direction. The Bond movies are tightly managed affairs, so once “Jaws” became the highest-grossing movie of all time, Spielberg probably would’ve dropped out. But a Spielberg-directed Bond was a genuine possibility, and “The Spy Who Loved Me” had the best screenplay of the Moore era. This could’ve been special.

 
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Steven Spielberg made "Interstellar"?

Steven Spielberg made "Interstellar"?
Paramount

The pairing of Hollywood’s master escapist with one of the world’s foremost theoretical physicists promised to transport audiences across the cosmos and through wormholes to galactic destinations unknown. With Jonathan Nolan writing the screenplay, sci-fi fans were geared up for something heady and strange. The project was eventually entrusted to Christopher Nolan, who delivered a brain-bending journey through time and space (and into the back end of a bookshelf). The finished product was terrific. But you can’t help but wonder how Spielberg would’ve depicted the event horizon and the tesseract (and if he would’ve made this yet another father-son story). Nolan’s film is emotionally cool, whereas Spielberg, even at his most cynical (“Munich”), always finds a touch of warmth.

 
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David Cronenberg made "Total Recall"?

David Cronenberg made "Total Recall"?
Tri-Star

Flush with the success of “Alien”, screenwriters Dan O’Bannon and Ronald Shussett finally had enough clout to get their widely praised adaptation of Philip K. Dıck’s “We Can Remember It for You Wholesale” before cameras. Producer Dino De Laurentiis acquired the rights and gave the project to David Cronenberg, who envisioned an intellectual sci-fi epic starring William Hurt. There’s conceptual art out there, and it looks nothing like Paul Verhoeven’s glossy, comic-book take on the material (which is wonderful in its own right). The trouble with Cronenberg’s version was its faithfulness to Dıck’s story; the screenwriters and De Laurentiis wanted “Raiders of the Lost Ark Go to Mars” (Cronenberg later joked he was making “Spider Goes to Mars”). There are elements of Cronenberg’s adaptation in “Total Recall”, namely the psychic belly mutant Kuato (who looks like something straight out of “The Brood”).

 
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James Dean?

James Dean?
Warner Bros

James Dean only lived to see his first major star turn (in Elia Kazan’s “East of Eden”) released. “Rebel Without a Cause” and “Giant” were posthumous sensations. Dean’s peculiar mix of danger and tenderness would’ve been perfect for the psychodramas of the 1960s. The inscrutable interiority he brought to his characters would’ve served him well as he transitioned from troubled youths to damaged adults. Every director in the world wanted to paint with his palette. He would’ve been brilliant in the conventional boxing biopic “Somebody Up There Likes Me”, but what about the florid, feverish team-ups that lay ahead with Nicholas Ray? What would his third act have looked like? He would’ve turned eighty this year. The absence of his voice in the choir is palpable.

 
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Carole Lombard?

Carole Lombard?
Warner Bros

The greatest screwball comedy actor of that glorious golden era was hitting her peak in 1942 when she perished in a plane crash during a war bond tour. Her performance in Ernst Lubitsch’s “To Be Or Not To Be”, released a month after her death, is a beguiling portrait of a bored star who drifts into a Polish resistance operation because she’s enamored of a young admirer. It’s a knowing variation on the free-spirited ditzes she played in “Twentieth Century” and “My Man Godfrey”; the Nazis are no match for her casually seductive charm. At the age of thirty-three, Lombard was on the brink of a brilliant second act. She could’ve done anything.

 
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Darren Aronofsky made "Batman: Year One?"

Darren Aronofsky made "Batman: Year One?"
Warner Bros

Darren Aronofsky's follow-up to “Requiem for a Dream” was supposed to be a gritty Caped Crusader reboot based on Frank Miller’s classic four-issue limited series. Origin tales are old hat nowadays, but in the early 2000s, a top-down cinematic reimagining of Batman would’ve been way ahead of the curve, and the perfect counterpart to Sam Raimi’s upbeat “Spider-Man” movies. According to one person who read the script, Gordon imbibes an ale, which results in extramarital shenanigans. Aronofsky approached Christian Bale to play Bruce Wayne, so this would’ve been a more canonical “Batman Begins”. Coming at such an early point in his career, it’s possible this would’ve shunted Aronofsky onto the studio blockbuster track. Do you want to live in a world with no “The Fountain”, “The Wrestler” or “mother!”? Exactly.

 
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Paul Verhoeven directed Arnold Schwarzenegger in "Crusade"?

Paul Verhoeven directed Arnold Schwarzenegger in "Crusade"?
Tri-Star

The “Total Recall” duo of Paul Verhoeven and Arnold Schwarzenegger was set to reteam in the early ‘90s on “Crusade”, a preposterously bloody action-drama about one of the bloodiest conflicts in human history. Working from a script by Walon Green (“The Wild Bunch”), the film would’ve almost certainly given a struggling Carolco the hit it needed to survive the debacle of “Cutthroat Island”. It also would’ve been a mess of gory combat that made “Braveheart” look like “A Room with a View”. The $100 million budget was exorbitant for the era, and medieval war movies were not the fashion, so, alas, it was not to be. Instead, we got “The Last Action Hero”. Maybe that works for you.

 
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John Belushi?

John Belushi?
Columbia

Had John Belushi the person followed the example of John Belushi the actor, he might still be with us today. After a wild five-year run on “Saturday Night Live” and hits like “Animal House” and “The Blues Brothers”, Belushi was beloved as an insatiable party machine. This couldn’t last. Belushi the actor understood this, and played against madman type in his final two films: the romantic comedy “Continental Divide” and the dark suburban farce “Neighbors”. Belushi’s drug appetite won out, but had he beat his demons there was a fascinatingly diverse career ahead of him. John Landis wanted him for a P.T. Barnum biopic, while Louis Malle had cast him in an (ultimately unmade) ABSCAM comedy. He had the chops for drama, and probably would’ve gone in that direction because who doesn’t love winning Oscars? He just couldn’t leave the party.

 
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Emily Lloyd hadn't turned down "Pretty Woman"?

Emily Lloyd hadn't turned down "Pretty Woman"?
Warner Bros

Emily Lloyd took the movie world by storm with her brazen portrayal of a free-spirited English teenager in the indie hit “Wish You Were Here”. She was preternaturally assured for a girl of fifteen, and Hollywood naturally had big plans for her. Just about everything went wrong from there. Nora Ephron’s mobster comedie “Cookie” was to be her U.S. breakthrough, but it stiffed at the box office. Presented with the option of starring in Garry Marshall’s “Pretty Woman” or co-starring alongside Cher in “Mermaids”, she chose the latter. Cher subsequently fired the director and Lloyd. Though she gave terrific performances over the next decade (particularly in “A River Runs Through It”), Lloyd’s career never recovered.

 
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O.J. Simpson played The Terminator?

O.J. Simpson played The Terminator?
ITC

The studio thought the retired, ultra-charismatic NFL star would cut an indelible figure as the robot sent from the future to kill the mother of the human resistance. Cameron did not believe the lovable Hertz spokesman would be believable as a murderer. Twelve jurors in a Los Angeles criminal court agreed.

 
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"Mission: Impossible 2" wrapped on time?

"Mission: Impossible 2" wrapped on time?
Lionsgate

Scottish actor Dougray Scott, who played the heavy in the second M:I movie, would be a household name as the X-Men’s Wolverine. Unfortunately, the Tom Cruise action flick required extra weeks of shooting, which knocked Scott out of the star-making role. The poor guy didn’t have a chance. He was under contract, and, to be fair, playing the big bad in a Cruise star vehicle wasn’t a horrible career choice. No worries. A few years later, he was rumored as the frontrunner to succeed Pierce Brosnan as James Bond. That went well.

 
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20th Century Fox greenlit Vincent Ward's wacky "Alien 3"?

20th Century Fox greenlit Vincent Ward's wacky "Alien 3"?
20th Century Fox

The New Zealand visionary blew cinephiles’ minds with his 1988 fantasy “The Navigator”. This clearly marked the arrival of a startlingly gifted new talent. Producers David Giler and Walter Hill took note and went to bat for the filmmaker to helm the third “Alien” movie. Ward’s vision was of a wooden planet tended to by monks. Yes, you read that correctly. A wooden planet. Love or hate David Fincher’s “Alien 3”, you’d have to be out of your gourd to not want to see a space epic set on a wooden planet. If this gets made, maybe we get more wooden planets. Perhaps a wooden galaxy. Space and wood: let’s make this happen!

 
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David Lean's lived long enough to make "Nostromo"?

David Lean's lived long enough to make "Nostromo"?
Columbia Pictures

This was to be the legendary filmmaker’s final epic. An adaptation of Joseph Conrad’s novel about silver smuggling in South America, Lean worked with Christopher Hampton and his “Lawrence of Arabia” screenwriter Robert Bolt to beat the script into shape. There was great enthusiasm about getting the film before cameras (Lean was, after all, Lean), but logistics and, ultimately, the filmmaker’s health got in the way. When Lean died in 1991, the project died with him. Had he mustered the strength and financing to complete the film, it would’ve been a real-life version of “The Tempest”. The master returns breaks his staff and recedes.

 
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Marilyn Monroe?

Marilyn Monroe?
20th Century Fox

The “what if” here is less about what was to come, and more about how Monroe’s career would’ve played out had she not been treated strictly as an object of desire. We know she was smart and savvy, but she was no match for the men in power who wanted to possess her. She was treated as a commodity; she was expected to be Marilyn Monroe in every movie, and when that faded she would be discarded. She gives a sad, soulful performance in her final film, “The Misfits”, which also served as Clark Gable’s big-screen farewell. So many Hollywood “what ifs” center on how things might’ve gone down differently had the world been a slightly less malicious place. Monroe deserved better.

Jeremy Smith is a freelance entertainment writer and the author of "George Clooney: Anatomy of an Actor". His second book, "When It Was Cool", is due out in 2021.

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