Leonardo DiCaprio – Crawley's Casting Calls

Shawn Phelan, Grand, TV, 1990. Confessions, confessions. Allison Jones, #1 casting director of comedies (by Judd Apatow, Paul Feig, etc) told The New Yorker in 2015 how she was told to pass on Leonardo DiCaprio in the short lived series. The role was the episode’s title, Wolf Boy: a Truffautian teenager raised by forest wolves. Jones never liked working for the networks. Too many suits. Too many opinions. For example, a writer complained that DiCaprio and the other kids looked too well-fed. (When she suggested Jim Carrey for another show, his mouth was too big). After 16 screen roles in 15 years, young Phelan suffered traumatic brain injury in car smash on March 29, 1994, remaining in a coma until dying at age 23 on September 27, 1998.
Jay R. Ferguson, The Outsiders, TV, 1990. Looking more ten than 15, Leo lost Ponyboy Curtis to the future Mad Men actor – and was compensated with another role in the pilot. The series died after 13 weeks. Leo’s test was among 54 such tapes banned from auction in Beverly Hills by the actors’ union in April 2013. “Auditions are not public performances,” said the SAG-AFTRA. “Performers are entitled to expect them to remain private.”
Chris O’Donnell, Scent of a Woman, 1991. All the young turks were in the pot for Charlie, the prep schooler babysitting a blind Al Pacino (finally winning his Oscar). DiCaprio, Ben Affleck, Randall Batinkoff, Matt Damon, Leonardo DiCaprio, Stephen Dorff, Brendan Fraser, Cole Hauser, Anthony Rapp, Sam Rockwell and Christopher Serrone.
Jeremy Jackson, Baywatch, TV, 1991-1999. More like Babewatch! When Brandon Cail jumped ship (or beach) after 21 episodes to join the Step by Step sitcom, the search for the new, son of the series star David Hasselhoff, ranged from Jackson… to Leo. During his 159 (or the 220) episodes, Jackson”s Hobie grew from kid to lover of one of his Dad’s red swimsuited lifeguard beauties, Shawn Weatherly as Jill Riley
Joshua Jackson, The Mighty Ducks (UK: Champions), 1992. Shooting from January 22 to April 11 to be precise. Hard to imagine but Leo was unknown back in the day and it wasn’t him, nor his agent but his parents who rejected the seen-it-all-before sports movie about, this timne, a kids’ team in the Pee Wee ice hockey leagues. Jake Gyllenhaal was also in the puck mix.
Omri Kastz, Hocus Pocus, 1993.
Something told him: Don’t do this movie. “There is a lot of luck and timing. But that’s not all of it. You know that quote: We stand on the shoulders of giants. Had I not had a contemplation or an understanding of all the greatness that had been done in cinema, had I not given myself a cinematic history lesson, on my own, I wouldn’t have known what to compare it to. I remember jumping around with Toby Maguire and Kevin Connolly in the trailer of their TV show Great Scott… rocking the air stream, because I got the part in Gilbert Grape. I’d done This Boy’s Life, and they’d given me the offer for Hocus Pocus, and I’d told them no. I wanted Gilbert Grape. It was a gamble, because I’d never had any real money in my life, and it was the first real money offer I’d ever gotten. I was 16 or 17. I look back and I don’t know how I, at that point, could have made that decision. I still didn’t have a home. We were renting a house… I remember, at 15… obsessively sitting in my bedroom watching every VHS tape I could rent. Just going to the video store all day long… After watching those movies, I just felt, ‘Holy shit, I’ve got one shot to be in this business, and I got a movie with Robert De Niro. I won the fucking lottery. So what are you going to do with that, kid? You have this path in front of you…’ Who knows?’ Maybe that other movie could have been great… Honestly, everything I’ve done was informed by watching those movies. Everything.” (DiCaprio was discussing his career with LA’s finest journo, Deadline Hollywood Mike Fleming Jr, February 10, 2016).
Chris O’Donnell, Batman Forever, 1994.
Chris O’Donnell, Mad Love, 1994. He’d just broken through as Johnny Depp’s kid brother in What’s Eating Gilbert Grape, so Leo was none too keen on daffy comedies with Drew Barrymore… Which could be seen as a Graduate sequel. The young lovers run away, her parents find her and shove her in a mental home, he springs her loose and and there they go, on the road again.
Michael Rappaport, Higher Learning, 1995. Split for The Quick and The Dead Western where star-producer Sharon Stone was paying him out of her own pocket.
Joaquin Phoenix, To Die For, 1995. In the mix when Gus Van Sant wanted Patricia Arquette in the lead. Joaquin is the brother of River Phoenix, star of Van Sant’s My Private Idaho; Leo inherited Rimbaud in Total Eclipse, 1995, after the River’s death in 1993. “When I started acting again, and going to auditions” said Phoenix, ” I’d always get to like the final callback, And there would always be, like, two other guys that I was up against. And we’d always lose to this one kid. No actor would ever say his name because it was, like, too much, but every casting director would whisper: It’s Leonardo.”
Edward Norton, Primal Fear, 1995. Every young star’s nightmare. He says no and instead of seeing it going to one of the usual rivals, the director finds a totally new kid, fresh out of Yale… and he wins an Oscar nod. Tired of waiting so long for a suitable youngster, Richard Gere almost quit.
Mark Wahlberg, Boogie Nights, 1997. Director Paul Thomas Anderson’s exploration of the 70s porno biz as a family unit (Burt Reynolds’ film-maker and Julianne Moore’s porno star being “the parents”) needed a stud called Dirk Diggler, loosely based on hungalike John C Holmes. Ben Affleck, Christian Bale, Matt Damon (!), Ethan Hawke, Jason Lee and Joachim Phoenix refused. Idem for, of all people, Vincent Gallo, seen in a hard-core fellatio scene in his rown Brown Bunnymovie in 2002. First choice was Leonardo DiCaprio. He loved the script but had a ticket the Titanica nd told PTA: “You should get Mark”… who kept his prosthetic penis. (In his Brown Bunny, Gallo proved he didn’t need one).
Matt Damon, Good Will Hunting, 1997. Director Michael Mann loved the script by Matt Damon and Ben Affleck, just didn’t want them as Will and Chuckie – written, Rocky-style for themselves. His only thought (and Rob Reiner’s for awhile) was: Brad ’n’ Leo – Pitt and DiCaprio.
Robert Downey Jr, Two Girls and a Guy, 1997. Legends are often two-sided. For example: aueturJames Toback, who had made two films with Downey, promised to be the first in LA to offer his pal a movie once he got out of rehab – and wrote this script for him in four days. And yet… an unavailable Leo was also asked to play Blake.
Vince Vaughn, Psycho, 1997.
By 1990, Anthony Perkins had played Norman Bates four times. So why should anyone else play him? It’s been (over)done. It’s a classic. And by The Master. Why re-make Hitchcock? Ah, beg pardon, Gus Van Sant called it a reproduction. A bizarre (lazy!) notion of copying – the Psycho script, word for word, action for action, move for move, shock for shock (except the shocks were too famous to shock anymore). “Just shoot it in color and have, for instance, Jack Nicholson play the detective and Timothy Hutton play Norman Bates,” he suggested. “Universal wanted to rope me in, and I said:“Here’s the idea: don’t change anything! It’s never been done before. Isn’t that a great reason to try it?” Not really! What had he said about re-makes? “The essence is missing. You might as well make an original movie.” Right! “One guy in particular has an extreme Tony Perkins quality – Robert Sean Leonard,” Van Sant told Movieline’s Stephen Rebello. “ So do… Henry Thomas and Jeremy Davies. [Indeed, Thomas was the teenage Bates in Psycho IV: The Beginning, 1989]. I think of Matt Damon for everything I do… But he’s one of those under-30 guys who just didn’t get it. Leonardo would have been fantastic. I knew he knew that he could step into it. But I also knew he didn’t really want to do it. I seriously considered Joaquin Phoenix. He was interested… but busy. So, it was either wait or forge ahead and we forged ahead. Vince was not even in my imagination… But he had a really interesting quality I wasn’t expecting.”The UK’s fast-rising Christian Bale and DiCaprio pal, Tobey Maguire, were also short-listed.
James Caviezel, The Thin Red Line, 1998. High on Terrence Malick’s comeback, DiCaprio took time off from Romeo + Juliet in Mexico to fly to Austin, Texas, for a meet in the American Airlines salon. Shades of Howard Hughes!
Edward Furlong, Pecker, 1998. As per usual, John Waters’ title was funnier than his script. His guy was called Pecker because… he pecked, like a bird, at his food. So why not Birdy?
Tobey Maguire, Ride With The Devil, 1998. Taiwanese Ang Lee’s take on the US Civil War – “like Bosnia or Vietnam, yet it was dead-centre USA.”
Adrien Brody, Summer of Sam, 1998. Leo and Benicio Del Toro were first choices for the leads finally given to Brody and John Leguizamo in Spike Lee’s look at the victims of the serial killer during the terrifying New York summer of ’77. A film, said Chicago critic Roger Ebert, vibrating with fear, guilt and lust.
Tobey Maguire, The Cider House Rules, 1998. Author John Irving went through four directors before settling on the Swedish Lasse Hallström to handle what Roger Ebert called a David Copperfieldish story (or, indeed, stories). For Homer, finally leaving his orphanage and surrogate father Michael Caine (winning his first Oscar), Hallstrom looked at The Class of ‘97 – Ben Affleck, Matt Damon, James Franco, Joseph Gordon-Levitt, Jake Gyllenhaal, Ethan Hawke, Edward Norton, Ryan Phillippe, Mark Wahlberg, Paul Walker. And chose Leonardo DiCaprio, who passed it to his (monotoned) pal, Maguire.
Nick Stahl, The Thin Red Line, 1998. Numerous stars – Clooney, Depp, Oldman, Pacino, Pitt, Rourke, Martin Sheen, etc – were almost queuing up, offering their services (even for free) for wizard auteur Terrence Malick’s first movie since Days of Heaven… 21 years before! (Sidney Lumet had earlier come close to filming “the best novel of war.”) Leo even took time off from Romeo + Juliet in Mexico to fly to Austin, Texas, for a meet in the American Airlines salon. Shades of Howard Hughes!
Matt Damon, The Talented Mr. Ripley, 1998. Anthony Minghella turned down Leo and his pal, Tobey Maguire.
Keanu Reeves, The Matrix, 1998. “Too many special effects,” complained Leo… The score’s composer Don Davis said Johnny Depp was first choice of the Wachowski siblings (then brothers Larry and Andy, now sisters Lana and Lilly). Warners voted: Brad Pitt or Val Kilmer. They passed. OK, said Warners: Depp or Keanu Reeves.  (As if that was a choice). Also seen for the neo-noir Neo: Nicolas Cage (family commitments), David Duchovny (preferred TV’s X-Files), Ewan McGregor (shooting Star Wars: Episode 1), Lou Diamond Phillips (his agent said: instant flop) and the surprisingly honest Will Smith – “I would have messed it up!”
Brendan Fraser, The Mummy, 1998. A surprise winner, particularly as it starred Fraser instead of… Ben Affleck or Matt Damon (they’d just won their Goodwill Hunting script Oscar), Evil Dead’s Bruce Campbell (his first studio offer), Leonardo DiCaprio (keen but tied to The Beach), the unknown Stephen Dunham (he debuted as Henderson), Matthew McConaughey, Chris O’Donnell, Brad Pitt, Kurt Russell, Sylvester Stallone and the star of the 2016 flop, Tom Cruise. Not as the titular Imhotep, of course, but the heroic Indiana…er… Rick O’Connell. Question: would Martin Scorsese have ever made five films with the guy from The Mummy?
Christian Bale, American Psycho, 1999. Bale, Spielberg’s Empire of the Sun kid, was all set for Mary Harron’s version of Brett Easton Ellis’ hardcore novel about a yuppy serial killer. when suddenly at the 1998 Cannes film festival, Lions Gate Films announced a $21m. deal with the Titanic supernova – who then wanted Stanley Kubrick, Martin Scorsese or Oliver Stone to direct! News to Bale, Harron and producer Ed Pressman. To Leo, as well. Or, that was his manager’s spin when Leo got bad press for for pushing Bale out. So, Leo quit for The Beach (pushing Ewan McGregor out!). and did his own kind of Bateman as Jordan Belfort in Scorsese’s comedy-noir, The Wolf of Wall, Street, 2012.
John Leguizmo, Summer of Sam, 1999. Spike Lee spins back to the summer of ’77 won Leo’s Romeo + Juliet co-star.
Ethan Hawke, Snow Falling on Cedars, 1999. Saw the Uganda born director Scott Hicks (of Shine fame) but refused the hero named Ishmael.
Keanu Reeves, The Matrix, 1999. Leo as Neo.  He had too much charisma for a cypher.
Matt Damon, All The Pretty Horses, 2000. Papers called it Titanic Goes West when DiCaprio’s people were demanding his new pay-cheque of $20m in 1998. Damon, a great fan of the book, was paid $6m. “I loved it. I wish I could do that movie forever. I have never felt that way about anything ever before.” Until producer Harvey Weinstein – aka Edwards Scissorhands (and much else) – tore it to pieces. Said Damon: “You can’t cut 35% of the movie and expect it to be the same movie.”
Ewan McGregor, Moulin Rouge, 2000. He didn’t even need his director pal Baz Luhrmann to tell him that his atrocious singing voice (his words) blew his chances of a lead role. A dozen hyars later, Luhrmann called up his Romeo for The Great Gatsby. No singing required!
Mark Wahlberg, Planet of the Apes, 2000. It was dial-a-hero time at Fox as, Ben Affleck, Kevin Costner, Matt Damon, Leonardo DiCaprio, Harrison Ford, Arnold Schwarzenegger and Patrick Swayze were contacted for the Charlton Heston substitute, Captain Leo Davidson, in the unnecessary re-hash of the 1967 classic. “It is what it is,” said a disappointed Wahlberg.“ They didn’t have the script right. Fox had a release date before Tim Burton had shot a foot of film. They were pushing him and pushing him in the wrong direction. You have to let Tim do his thing.”
James Franco, James Dean, TV, 2001.
Leo was in the the Jimmy mix with Brendan Fraser (!), Edward Furlong, Gary Oldman, Brad Pitt.. and Leonardo DiCaprip. “I did a screen test,” he told Deadline’s Mike Fleming. “I think I was 18. It turned out pretty well. We saw clips of Giant, and then he put me in the back of the car with that cowboy hat. But I was a very young looking kid… He decided to wait a couple of years, but I… looked really young.” “He” was director Michael Mann, who also spoke with Fleming. “It was a brilliant screenplay. And then it’s who the hell could play James Dean? And I found a chap who could… But he was too young. It was Leo. We did a screentest that’s quite amazing… He would turn his face in one direction and we see a vision of James Dean, and then he’d turn his face another direction and it’s no, that’s a young kid.” With both guys talking to Fleming, the Hollywood Elsewhere blogger Jeffrey Welles broke a long silence… about Mann actually showing him the 1993 test. “It was filmed footage on a VHS cassette. Leo was wearing a red Rebel Without a Cause jacket and ‘50s Brylcream pompadour hair. The deal was that I couldn’t mention to anyone (not even my mother) that I’d seen it, and there could certainly be no filing of any kind. I agreed, of course, but I was so knocked out by how well DiCaprio had captured Dean’s expressions during his big scene with Jo Van Fleet in East of Eden .I was so turned around that it broke my heart to have to sit on my impressions forever. But [now], it seems okay to mention my quick peek.”
Sam Rockwell, Charlie’s Angels, 2000. Drew Barrymore bought the movie rights and proved herself as star and producer. Chasing, for example, Leo for kidnap victim Eric Knox, the software genius head honcho of Knox Enterprises. Leo’s dance-card was full. Enter: Rockwell. Both actors had Oscars in their futures… Leo had made first theatrical release, Poison Ivy, with Barrymore in 1991. He was credited as: Guy. And the cameo was so short, it was cut from the final cut!
Adrian Grenier, Havard Man, 2001. Met twice with writer-director James Toback about his script seven years earlier. “He suddenly flops down on the couch in the fetal position, fingers flicking pianistically on his thigh. Then, he jumps up as if startled by a noise.” (A perfect imitation of Harvey Keitel in Toback’s Fingers). “This,” continued Toback’s diary, “is one brilliant motherfucker.”
Tobey Maguire, Spider-Man, 2001.
Hayden Christiansen, Star Wars: Episode II – Attack of the Clones, 2001.
Jude Law, Cold Mountain, 2002. Too cold! Romance, friendship and war as a wounded confederate soldier, Inman, tries to return to his North Carolina mountain and his gal, Nicole Kidman as Ada.
Brendan Fraser, Looney Tunes: Back in Action, 2002. “A pretty grim experience all around – longest year and a half of my life.” Director Joe Dante refusing to say anymore about how his planned tribute to his late friend, toon ikon Chuck Jones, ended up a mess. Then again, when the suits approve Fraser over Leo, George Clooney, Will Ferrell, Michael J Fox and Sylvester Stallone for DJ Drake, you know you’re in trouble.
Michael Pitt, The Dreamers, 2002. Italian director Bernardo Bertolucci’s dream Matthew, had to pass not (like Jake Gyllenhaal) due to the full frontal sex but prepping The Aviator, 2004, with Martin Scorsese. Pitt closely resembled Leo., but proved a more credible innocent.
Kevin Spacey, Beyond The Sea, 2003. “Let’s go for Leo – you’re too old to play Bobby Darin,” Paramount told Spacey in 2000. True, but he got neatly around that in his script. He also did his own singing. And writer-directed the movie. Beat that, Leo!
Tom Cruise, Collateral, 2003. No way, said Leo – tool busy crashing planes as the Aviator Howard Hughes The hitman in the back of Jamie Foxx’s cab changed – Leo, Colin Farrell, Edward Norton, John Travolta – almost as often as the thriller’s director. from Scorsese (making Aviator, instead) and Spielberg to Spike Lee and, finally, Michael Mann (one of the 18 Aviator producers).
Nick Stahl, Sin City, 2004. Aiming high, Robert Rodriguez first asked Leo to be Roarke Jr, aka The Yellow Bastard. Or, Blue Bastard on-set, because yellow, like green, reacts with the green screen, yadda, yadda…
Jake Gyllenhaal, Jarhead, 2004. Considered, alongside his mate Tobey Maguire, for US Marine Anthony ”Swoff” Swofford, who wrote of Desert Storm: “Whatever else he may do with his life – build a house, love a woman, change his son’s diaper – he will always be a jarhead.” Also in the Swoff mix: Emile Hirsch, Josh Hartnett, Joshua Jackson and Shane West.
Heath Ledger, Brokeback Mountain, 2004.
Hollywood was not keen on Annie Prouix’s 1977 short story – two gay shepherds in Wyoming, get outa here! Until directors (more than actors) queued to make it. Ang Lee, Joel Schumacher – but first in line was Gus Van Sant (obviously). He called up Damon and Joaquin Phoenix (obviously, they’d made his Good Will Hunting and To Die For, respectively). Said Damon: “Gus, I did a gay movie [The Talented Mr Ripley, then a cowboy movie [All the Pretty Horses]. I can’t follow it up with a gay-cowboy movie!” Ang Lee was considering retirement when the script “nurtured” him back to work, only to find many actors were scared to play gay. Leo, Ryan Philippe and Brad Pitt all refused. Heath Ledger and Jake Gyllenhaal did not. ”These two are among the best in their age group.. Jake plays the opposite of Heath and it creates a very good couple in terms of a romantic love story.” Gyllenhaal added: “I don’t think that these two characters even know what gay is.… What ties [them] together is not just a love, but … primarily it was deep loneliness.” Ang Lee told journo Robert Ordona that in the 60s, he’d have chosen Paul Newman and Montgomery Clift as Ennis and Jack.
Emile Hirsch, Alpha Dog, 2006. Auteur Nick Cassavetes considered Leo for Jesse James Hollywood – or Johnny Truelove here, in a reconstruction of his kidnapping and slaughter of Nicholas Markopwitz (re-named Zacl Mazursky fort Antpn Yelchin). Grisly story, grisly film – stolen by a wondrous turn from Justin Timberlake.
Matt Damon, The Good Shepherd, 2006. It was 14 years since Robert De Niro directed the very young Leo in A Boy’s Life – but now he’d succeeded De Niro as Martin Scorsese’s steady star. Hence, he preferred The Departed ensemble to this De Niro’s pet project for a decade: the life of the real founder of the CIA, James “Jesus” Angelton. Somehow, Matt made both.
Will Smith, Hancock, 2007. Collecting dust on Hollywood shelves for a rapidlyl decade as Tonight, He Comes, Vincent Ngo’s script (much darker, with Hancock unable to to have sex without killing his lovers) had the finger smudges of George Clooney and close pals Ben Affleck and Matt Damon.
Emile Hirsch, Into The Wild, 2007.   When first keen on adapting-directing Jon Krakauer’s novel, Sean Penn wanted Leo as Christopher McCandless on a Kerouac road and Brando as his most touching contact, who sees him as a wayward grandson.
Ewan McGregor, Angels & Demons, 2008. Despite being invited by his old Catch Me If You Can co-star Tom Hanks to join the Dan Brown project, Leo passed on the Hanks-is-symbologist-Robert Langdon sequel. Hence, the Scottish McG inherited the Irish Camerlengo Patrick McKenna. And stole the entire enterprise.
Christoph Waltz, Inglorious Basterds, 2008. Leo was Quentin Tarantino’s initial choice for for Standartenführer Hans Landa in his Wild Bunch take on The Dirty Dozen, until deciding it required a German actor. Unable to find one to suit the “unplayable” role, he came close to abandoning his ninth movie until meeting Waltz. “He gave me my movie!” And was rewarded with a support acting Oscar – same again for the next Tarantino, Django Unchained, 2011, wherein Leo played a similarly loquacious Landaesque villain.
Johnny Depp, Public Enemies, 2009. First on board as Public Enemy #1 John Dillinger when the project came up, circa 2004.
Jude Law, Repo Men, 2009. Leo changed direction left the year 2025 and a never paid for heart transplant to Law & Son – eleven-year-old Raff playing the young Jude.
Ryan Gosling, The Ides of March, 2010. George Clooney shelved his fourth entry as a director in 2008 when Beau Williamson’s Farragut North play was suddenly too cynical during the optimism of Barack Obama;’s becoming US President. Therefore, he lost Leo, his co-producer, as a Sammy Glickish spinmeister doing anything to win the presidential nomination for his candidate (Clooney in a role referred to but never seen in the play). Chris Pine was chased before Gosling took over.
Aaron Johnson, Savages, 2011. Leo was far too busy to take up Oliver Stone’s drama about two pals growing such great pot that a Mexican drug cartel threatens to kill their girl unless the guys work for them.
Joseph Gordon-Levitt, The Dark Knight Rises, 2011.
Chris Pine, Rise of the Guardians, 2011. Jason Bateman, Leonardo DiCaprio, Sam Rockwell and Jim Sturgess were on the voice list for Jack Frost in the DreamWorks toon about saving childhood, itself, from Jude Law’s dreaded Pitch Black. Other guardians included Easter Bunny, Tooth Fairy and a Santa Claus complete with tatts and a Russian accent!
Brad Pitt, World War Z, 2012. Max Brooks’ book about a zombie pandemic (!) was fought over by Leo and Brad Pitt’s combines. Plan B won – ie Pitt.
Christian Bale, Out of the Furnace, 2012. Due for the lead – an ex-con haunted by his past – until Quentin Tarantino unchained Django. Leo’s His company, Appian Way, co-produced.
Jack Gyllenhaal Prisoners, 2013. Attached, as they say, during the project’s four year on/off Hollywood shelf life. Jake had starred in the French-Canadian director Denis Villeneuve’s previous movie, Enemy.
Henry Cavill, The Man From UNCLE, 2013. Superman Cavill goes Solo. Napoleon Solo… After securing the 60s’ TV series rights in 1993, producer John Davis went through 20 years, 14 scripts, four directors (letting slip Soderbergh and Tarantino!), plus 19 Napoleon Solos. From George Clooney in 2010 to Tom Cruise three years later. By way of the early-21st century suspects: DiCaprio, Christian Bale, Bradley Cooper, Matt Damon, Joel Edgerton, Michael Fassbender, Joseph Gordon-Levitt, Ryan Gosling, Jon Hamm, Joel Kinnaman, Ewan McGregor, Robert Pattinson, Chris Pine, Ryan Reynolds, Alexander Skarsgård (he switched to Tarzan), Channing Tatum. Even Russell Crowe, surely a better bet at 50 for old Waverly, the UNCLE boss. Poor Davis never got it right!
Samuel L Jackson, Kingsman: Secret Service, 2013. Hey, Leo, howda like to be the villain? Been there, done that, got the Tarantino tee-shirt! The not-007-but… thriller was directed by Matthew Vaughn, who created the sixth James Bond with the 2003 choice of Daniel Craig for Layer Cake – “My name? If you knew that, you’d be as clever as me.”
Benedict Cumberbatch, The Imitation Games, 2013. Leo was first choice, but Cumberbatch was better for the tragic tale of UK mathematician Alan Turing. He helped crack the Enigma code during World War II. Was hailed as a hero and chemically castrated for being homosexual – “a really shameful, disgraceful part of our history,” said Cumberbatch.
Mark Wahlberg, The Gambler, 2014. Wahlberg, who has had his (few) moments on-screen, lost 61 lbs for his addict rôle of a lifetime in the totally unnecessary re-tread of James Toback’s autobio study with James Caan in 1974. Now if Plan A had gone ahead – Leo and Martin Scorsese, together again – that have been something.
Billy Crudup, The Stanford Prison Experiment, 2014. Despite being (a) minus superheroes and (b) based on a 1992 documentary, among other films, TV episodes and mangas influenced by the SPE, Hollywood was bedazzled by the awful tale and De Caprio was keen on playing Dr Philip Zimbardo, studying the psychological effects of jail on prisoners and warders. In 1971, he literally incarcerated 24 students in a Stanford U basement and watched an epic power-play nightmare unfold… not far removed from the horrors perpetrated by US Amy and CIA in Iraq’s Abu Ghraib prison as revealed in 2003.
Michael Fassbender, Steve Jobs, 2015. Christian Bale was in, then out (like Sony Pictures!). Other potential Apple visionaries included Bradley Cooper, Matt Damon and DiCaprio. Christian baled for The Accountant and Leo took over another Bale reject,The Revenant… before “a lengthy break from acting.” “Horrible behaviour,” said producer Mark Gordon. “Actually despicable,” replied Sony production chief Amy Pascal… in hacked emails leaked in December 2014. Then, Fassbender proved available. Luckily for director Danny Boyle. Leo knew what he was doing. He won his Oscar – and Alejandro G Iñárritua got his second in a row – for Revenant.
James McAvoy, Split, 2015.
When Joaquin Phoenix could not reach a deal, auteur M Night Shyamalan met McAvoy by chance at a Comic-Con. The Scottish actor agreed to play the Billy Milligan (1955–2014), diagnosed with 24 multiple personalities (ten desirables,13 no), including two women and a girl of three. Charged with raping three women in 1977, Milligan was acquitted when his defence argued that the crimes were committed, not by Milligan, but by one of his alternate personalities. “Hitchcock created a masterpiece using the same subject matter to create Psycho,” noted critic Dennis Schwarz, “but Shyamalan is only a so-so director and just comes up with an unpleasant and pointless kidnapping thriller.” David Fincher and Joel Schumacher were previously attached to another version, The Crowded Room, with such potential Milligans as Jim Carey, John Cusack, Johnny Depp, Leonardo DiCaprio (producing his version), Matthew McConaughey, Sean Penn and Brad Pitt for the producer called Leo.
Ben Affleck, Live By Night, 2015. When deciding to simply produce, Di Caprio passed the lead to Affleck – who wrote, directed and co-produced with Leo’s company. Author Dennis Lehane was not sure Affleck could portray the deceitfulness, modesty and shame of Prohibition “bandit” Joe Coughlin until Ben won him over by agreeing to test. (It must have been better than his one trick pony acting in the film). Finally, Warner Bros ruined it all by slashing Affleck’s three hour cut from a character study to action movie.
Will Smith, Suicide Squad, 2015. After seeing 14 possible Harley Quinns, director David Ayer shuffled through 19 Deadshots. None hit the target. Not Leo, Daniel Craig, Matt Damon, Johnny Depp, Idris Elba, Colin Farrell, Michael Fassbender, Joseph Gordon-Levitt and Jon Hamm. Nor Oscar Isaac, Joel Kinnaman (he became Rick Flag), Matthew McConaughey, Ewan McGregor, Robert Pattinson, Brad Pitt, Keanu Reeves, Alexander Skarsgård and Jason Statham. Another Warner/DC flop because Warner wasn’t Marvel and Smith was way too top-heavy for a team effort.
Jason Momoa, Aquaman, 2017. Di Caprio had always been keen to produce and if necessry star in an aquafilm. Over the years, Matt Damon and Simon Baker were also in the swim… before Momoa was announced on October 15, 2014… for 2018 summer release.
Charlie Hunnam,Triple Frontier, 2019. Five buddies take down a South American drug lord. But which magnificent five? Well, it was only the squad leaders mentioned – one wrinklie, one younger –as the script lay on the ropes for eight years, going from directors Kathleen Bigelow to JC Chandor and from Paramount to, but of course, Netflix. Tom Hanks-Johnny Depp were the 2010 duo, followed by Denzel Washington-Sean Penn, Tom Hardy-Channing Tatum, plus Ben Affleck and his bro, Casey. And finally Ben Affleck-Hunnam. Leonardo DiCaprio, Will Smith and Mark Wahlberg also featured in the mixes – minus any cited pardner.
Bradley Cooper, Licorice Pizza, 2020. Poor Leo. He was offered the role of the real Hollywood producer Jon Peters by Paul Thomas Anderson… at the same as Guillermo del Toro asked him to take the lead his Nightmare Alley. What to do, what to do…? Neither!
Bradley Cooper, Nightmare Alley, 2020. “He was interested because we have a common fascination for the carnival,” Mexican director Guillermo de Tro told The Wrap about his re-hash of Tyrone Power’s 1947 thriller – Ty’s favourite movie. “But very quickly… it was evident that there was gonna be a conflict of dates.” He needed enough time to gather his dreamwish cast. He’d written Lilith for Cate Blanchett, Clem for Willem Dafoe and Bruno for Ron Perlman (for the seventh time). “So we couldn’t be hurried into shooting… we needed to make all these schedules coalesce into the movie.” In the end, Bradley Cooper played both Alley’s Stan Carlisle and PTA’s Jon Peters… Ironically, Peters had produced the fourth A Star Is Born, 1975, while Cooper actor-directed the fifth in 2017. And just to add to the muddle, one Pizza actor is called… Paul Anderson.
Brad Pitt, Babylon, 2021. Leo’s pal Tobey Maguire was among the nine producers so, of course, he called up Leo. But he was over-scheduled. Therefore, Brad Pitt, coming off his Oscar for Tarantino’s Once Upon A Time… in Hollywood (with Leo) agreed to take another take on Film City… back when movies were changing from silents to talkes, ruining various careers in the process.
Adam Driver, House of Gucci, 2021. Ridley Scott’s Succession, Italian Style, had been on many shelves over the years. The role of Maurizio, the Gucci heir murdered on his ex-wife’s orders, was aimed at Leo – plus Batman and Captain America (Christian Bale and Chris Evans) – first reserves if Adam Driver couldn’t get free for his second consecutive Scott trip after The Last Duel, 2020. DiCaorio’s father would have been Robert De Niro in a once planned Martin Scorsese version

Birth year: Death year: Other name: Casting Calls: 74