- 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.”
- 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.
- 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, 1996. Director Paul Thomas Anderson’s exploration of the 70s porno biz as a family unit needed a stud called Dirk Diggler - loosely based on hungalike John C Holmes. “Got to me a little late, guys, just signed for Titanic. Know what? You should get Mark...” Leo regretted missing it, but he was just too wholesome and not smegma cheesy.
- 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.
- 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. Had to refuse his Gilbert Grape maker Lasse Hallstrom - but recommended his pal.
- 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. Hero Rick O’Connell was up between Ben Affleck, Matt Damon, Matthew McConnaughey, Chris O’Donnell, Sylvester Stallone. And Leo tried to postpone The Beach in order to make both movies. Impossible said his UK producers. 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.”
- 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!
- 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.
- Michael Pitt, The Dreamers, 2003. 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, 2004. “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!
- 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.”
- 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. Tom Hanks, star of the Dan Brown franchise, personally asked Leo to play Camerlengo Patrick McKenna. And Leo personably passed. In 2001, they had co-starred in Steven Spielberg’s Catch Me If You Can
- Christoph Waltz, Inglorious Basterds, 2008. Leo was first choice for Nazi officer Hans Landa until Quentin Tarantino felt a German-speaklng actor would be better. Leo became QT’s next villain - Calvin Candie in Django Unchained, 2012. With Waltz as the hero, an ex-dentist-turned -bounty hunter.
- 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. He was in director Miguel Sapochnik’s second feature. Then, he wasn’t. So it blows.
- 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. Leo was due to voice Jack Frost, but a crowded agenda forced him to quit during pre-production.
- 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, 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 andLeo 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.
- 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.