Jake Gyllenhaal


  1. Joshua Jackson, The Mighty Ducks (UK:Champions),1992.   Shooting from January 22 to April 11 to be precise.  Both Gyllenhaal and the then unknown Leonardo DiCaprio were in the puck mix for Charlie Conway in the seen-it-all-before sports movie about, this time, a kids’ team in Pee Wee ice hockey leagues. Leo’s parents rejccted the film on his behalf.  Wise folks.  

  2. Wes Bentley, American Beauty, 1998.     The Swedish-Ashkenazi Jewish “Jill-en-hall” from LA  was seen for the dark Ricky Fitt: “I’m the best piece of ass in three States.” Of course, he was considered. He was better known at the time as… Donnie Darko.  

  3. Tobey Maguire, The Cider House Rules, 1999. 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), Hallström 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. 

  4. Ewan McGregor, Moulin Rouge! 1999.   “It was soooo close. I sang and everything… through months of auditions. It was between me, Heath Ledger and Ewan.  I think it came down to age. I was the youngest and the least known. I would hope it didn’t have anything to do with talent. Maybe it did.” No, he was deemed too young to partner Catherine Zeta-Jones or Courtney Love or even, the final choice.  Nicole Kidman.  “They didn’t have to be big singers,”  director Baz Luhrmann explained about his needs for the 1890s Paris shot in Sydney! “But they had to be able to move you emotionally. Basically, Ewan and Nicole were the best for the job. That’s the bottom line of it.”  Baz had also glanced at  Hugh Jackman, Ronan Keating and the Northern Irish singer-songwriter Tim Wheeler.
  5. Heath Ledger, The Patriot, 2000.  After Braveheart, Mel Gibson tackles the American War of Independence… sans slavery!  Ledger, Gyllenhaal, Joshua Jackson, Ryan Phillippe, Freddie Prinz Jr, Brad Renfro, Paul Walker and Elijah Wood were seen for Gibson’s eldest son. Fed up with only being teenage beefcake, Ledger was about to quit acting and return down-under when he  won Gabriel.   Five years later, Gyllenhaal and Ledger were cock o’ the Hollywood walk as the Oscar-nominated gay shepherds in Brokeback Mountain.
  6. Tobey Maguire, Spider-Man, 2001.
  7. Elijah Wood, The Lord of the Rings trilogy, 2001-2003.
  8. Nick Stahl, Terminator 3: Rise of the Machines, 2002.   Stahl beat both Jake and Shane West in Chapter 3, but when asked to continue being John Connor in Chapter 4, Terminator Salvation, 2007, he shook the team by saying:“I don’t care really, to be honest. I don’t have much interest…Something like T3 was so unexpected… not something I can honestly say that I expected to be doing, given the films I’d been in before. Sometimes you find that there is better material in small and more independent movies… more risk-taking. I want to keep doing.”
  9. Tobey Maguire, Spider-Man 2, 2003.

  10. Michael Pitt, The Dreamers, 2003. 
    His agent said: “No frontal nudity.” Bertolucci replied: “No film.”  Leading lady Eva Green added: “Jakethought thatif he showed his penis in the film, he’d be considered a porno actor.” The DiCaprio-esque Pitt, from Dawson’s Creek, said the skintimacy required by Italian director Bernardo Bertolucci (of Last Tango In Paris fame…or infamy!) was not easy but that censorship “was the insecurity of a bunch of old men who feel uncomfortable if they see a young guy without clothes.” Or old women. Veteran actress Celeste Holm, 84, was rushed to hospital, after falling ill, “gasping for breath,” during the New York premiere.

  11. Christian Bale, Batman Begins, 2004.

  12. Brandon Routh, Superman Returns, 2006.

  13. Jim Sturgess, Across The Universe, 2006.      Director Julie Taymorconsidered the LA dude for Jude. As implied bytitle and characters (Dr Robert, JoJo, Lucy, Mr Kite, Prudence, Rita, Sadie) this was visually enchanting musical tribute to ($10m worth of) The Beatles’ music.“Where,” said Chicago critic Roger Ebert, “we walk into the theatre humming the songs.”

  14. Michael C Hall, Dexter, TV, 2006-2014.    The Showtime cable network shortlisted 14 stars, from the impossible (Dan Aykroyd, Macauley Culkin, Tom Cruise, Sean Penn, Ben Stiller) to the plausible (Gyllenhaal, John Cusack, James Spader) for the Miami Metro PD blood splatter analyst  moonlighting  as a serial killer… of serial killers.
  15. Aaron Eckhart, The Dark Knight, 2007.
  16. Zach Galifianakis,  The Hangover, 2008.   “We can’t find Doug!” No one  knew that losing the  bridegroom after his stag night would  smash  comedy records.  And go on to a three movie franchise.  So… #1. Knowall  Jack Black passed.  #2.  Gyllenhaal, Thomas Haden Church, Jonah  Hill  were looked over with apparent askance.   #3. Alan was retooled to suit  the exuberant Zach The Greek. 
  17. Sam Worthington, Avatar, 2008.   “For his (and Hollywood’s)  most  amazing  science fiction  film – it created an entire new planet –  James Cameron’s backers  wanted Gullenhaal, Matt Damon or Chrtis Pine (as the hero, Jake Scully. (“My worst audition ever,” said Pine).  Cameron preferred an unknown. “A guy you want to have a beer with…. who becomes a leader, transforming a whole world.” Cameron retained his title of the #1 film of all time (last time it was Titanic) with two giant sequels to come. And  all this inspried by  the 1995 Disney toon,  Pocahontus.  Poor Worthington was reduced to living in his car at the time…
  18. Bradley Cooper,  Valentine’s Day, 2009.    Orlando Bloom and Sam Worthington also passed on Holden – in the 21-star-jammed LA take on Love Actually. Director Garry Marshall struck gold – then re-made it (badly) as New Year’s Eve in New York.
  19. Seth Rogen, The Green Hornet, 2010.    When Miramax owned  the rights in 2001, the Weinstein brothers booked New Jersey auteur Kevin Smith to writer-direct – with  a green Jake. Scared of a  big budget, Smith fled. Paradoxically,  his chubby star of Zack and Miri Makes A Porno became the star – after Rogen heroically lost a terrifying 30 lbs. (Smith’s script finally saw the light of day in a comic book). During the  flop’s 14 year gestation, the others  keen on green were George Clooney, Ryan Gosling, Vince Vaughn, Mark Wahlberg…  and Corey Reynolds or Eddie Murphy for the black Hornet: John Stewart. 
  20. Ryan Reynolds, Safe House,  2011. All the new guys – Jake, Zac Efron, Andrew Garfield, Tom Hardy, Garrett Hedlund, Chris Hemsworth, Taylor Kitsch, Shia LaBeouf, James McAvoy, Chris Pine, Channing Tatum, Sam Worthington – angled to be the freshman CIA babysitter rescuing Denzel Washington in the  Hollywood debut of Swedish director Daniel Espinosa.

  21. Eddie Redmayne, Birdsong, TV, 2011.      It took the one-time 007 book writer Sebastian Faulks more than a decade toget his WW1 novel into cinemas. In 2006, he reported:  “All the original actors are now too old – Ralph Fiennes and before him Daniel Day-Lewis.   More recently they were talking about Orlando Bloom… By the time it gets made, the star of Harry Potter could end up being old enough for it – is he a good actor?”  Hollywood even insisted upon Gyllenhaal for the UK hero.   Finally, Working Title TV made it with BBC and NBC as a mini-series with the Old Etonian of the hour – from Tess of the D’Urbervilles, The Pillars of the Earth, My Week With Marilyn.
  22. Jeremy Renner, The Bourne Legacy, 2011.  Three was enough for Matt Damon. (Until 2015…!)  The studio did not agree and kept the franchise alive by rebooting Jason Bourne as Aaron Cross – “There Was Never Just One.” But who to play him from 20 hopefuls- Erryn Arkin, Adam Brody, Dominic  Cooper, Paul Dano, Luke Evans, Michael Fassbender, Jake Gyllenhaal, Josh Hartnett, Garrett Hedlund, Oscar Isaac (he was made an Outcome super-agent), Taylor Kitsch, Shia LaBeouf,  Kellan Lutz, Logan Marshall-Green, Alex Pettyfer, Michael Pitt and Benjamin Walker. Plus Joel Edgerton and  Tobey Maguire, who were Great Gatsbying  down-under. Renner, Hollywood’s new white hope since The Hurt Locker, 2009, was suggested  for the Mission: Impossible.. if ever Tom Cruise retired.    
  23. Sam Rockwell, The Way, Way Back, 2012.      Jake dropped out of the latest Steve Carell comedy and Sam dropped in.   “When it comes to a character,” explained Jake, “I’m moved by folk that I might struggle to love at first; characters that I have to do enough research on and think enough about to be able to really fall in love with them.”
  24. Mark Ruffalo, Now You See Me, 2012.    And now you don’t… Change of FBI agent Dylan Hobbs for French realisateur Louis Leterrier (The Incredible Hulk, Clash of the Titans) as the Fibis and Interpol try to snare some – here’s a first – illusionist bank robbers! 
  25. Chris Pine, Into The Woods, 2013.  
  26. Bradley Cooper, Jane Got a Gun, 2013.   Natalie Portman’s fifth outing as a producer ran into all kinds of trouble. Michael Fassbender quit (replaced by Joel Edgerton) after clashes with Scots director Lynne Ramsay. Then, she quit. Then, Jude Law quit Edgerton’s original role – Lynne being the only reason why Law had agreed to make the Western in Santa Fe. Bridges was the (way) oldest of Law’s potential successors: double the age of Jake, Tobey Maguire. (Ramsey’s exit allowed her to join Steven Spielberg’s 2013 Cannes festival jury).
  27. Bradley Cooper, Jane Got a Gun, 2013.  Natalie Portman’s fifth outing as a producer ran into all kinds of trouble.  Michael Fassbender quit  (replaced by Joel Edgerton) after clashes with Scots director Lynne Ramsay. Then, she quit. Then, Jude Law quit Edgerton’s original role –  Lynne  being  the only reason why Law had  agreed to make the Western in Santa Fe. Bridges was the (way) oldest of Law’s potential successors: doiuble  the age of Jake, Tobey Maguire. (Ramsey’s exit allowed her to join Steven Spielberg’s 2013 Cannes festival jury).
  28. Benedict Cumberbatch, Doctor Strange, 2014.    Discussed, planned, written, re-spun since 1986, always dropped despite scripts from Alex Cox, Wes Craven, Bob Gale, etc, until chosen as the  portal into the supernatural side of the Marvel Cinematic Universe.Mads Mikkelsen  was first choice. But that was in in 2013…  Among those later flown up the  flagpole were TV doctor Patrick Dempsey, Johnny Depp, Colin Farrell, Joseph Gordon-Levitt, Ryan Gosling, Jake Gyllenhaal, Jon Hamm, Tom Hardy, Ethan Hawke, Jack Huston, Oscar Isaac, Matthew McConaughey, Ewan McGregor, Vincent Price (in 1986!), Keanu Reeves (listed but never approached – how wise!), Justin Theroux. Oh and two Jokers: 2015’s Jared Leto and 2018’s Joachin Phoenix.  Finally, production wisely waited until after Cumberbatch’s Hamletstagetriumph in London. If Iron Man is Mick Jagger, Strange is Jim Morrison… and could be head of the MCU when Robert Downey pawned his ironmongery.
  29. Ryan Reynolds, Mississippi Grind, 2014.        Schedules clashed and Reynodls took over the gambling tale, greatly, er, inspired by Robert Altman’s 1974, California Split.  
  30. Joel Kinnaman, Suicide Squad, 2015.   First, Tom Hardy, then Gyllenhaal, Jon Bernthal, Jason Clarke, Joel Edgerton and Karl Urban – lotsa comings and goings for Rick Flagg Jr in DC’s Dirty Dozen,a black ops force of supervillains, forced, blackmailed or offered  deals to work for the US government. Hardy preferred Venom; Urban almost became Aquaman’s first villain.
  31. Michael Shannon, The Current War, 2016.       Witty title as this is about Thomas Edison and George Westinghouse creating an electrcity system for the USA. Benedict Cuimberbath was Edison, and Shannon took over Westinghouse from Gyllenhaal. Almost a Marvel movie, as Cumerbatch, Nicholas Hoult, and Tom Holland were, as far as kids were concerned, Dr Strange, Hal McCoy/Beast and Peter Parker.Spider-Man.






 Birth year: Death year: Other name: Casting Calls:  31