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Sean Penn


  1. Christopher Atkins, The Blue Lagoon, 1979.          The shipwrecked rolewas his - until Grease director Randal Kleiser’s team took one final review of the tests and notes of 4,000 hopefuls...
  2. Judge Reinhold, Fast Times at Ridgemont High, 1981.     The US high school movie..! Researched and written by Cameron Crowe, directed by Amy Heckerling. Before turned into the stoned surfer Jeff Spicily (who ordered pizzas delivered to his classroom),  Penn was in the Brad mix with Matthew Broderick, Nicolas Cage, Tom Hanks. It is not known, of course, but it’s likely that Penn would have used a dildo (like Reinhold) in his masturbation scene - so realistic it made co-star Phoebe Cates freak out. Her horrified expression is not acting! Didn’t stop her re-joining Reinhold in Gremlns in 1983.
  3. Kevin Costner, The Big Chill, 1983.        ESP?  Costner's role - the dead pal   whose funeral causes the class reunion - was left on the cutting-room floor.
  4. Tom Cruise, Top Gun, 1985.     Among those passing on cocky USNavy jet pilot Lieutenant Pete "Maverick" Mitchell  were: Penn, Kevin Bacon, Scott Baio, Matthew Broderick, Nicolas Cage, Jim Carrey, John Cusack, Robert Downey Jr, Michael J Fox, Rob Lowe, Matthew Modine (tookn exception to the script’s Cold War politics), Patrick Swayze, Eric Stolz John Travolta (too pricey). Plus Tom Hanks, old enough to be the CO at 29 - and brothers Charlie Sheen and Emilio Estevez. Too young, at 20, Sheen sent the whole movie up in Hot Shots! 1990. Maverick became one of Cruise’s signature acts - still  took 34 years for a sequel!
  5. Nicolas Cage, Peggy Sue Got Married, 1985.  Director Penny Marshall talked to Tom Hanks and Sean Penn about being the bridegroom Then, she was fired.  It’s too big for a first-timer, rasped the silly suits and called up Francis Ford Coppola (see what I mean about silly suits). Way too big for such a fairy-tale. Don Francey  chose his nephew. Wow, never saw that coming…  
  6. Mel Gibson, Lethal Weapon, 1986.     In all, 39 possibilities for the  off-kilter, ’Nam vet cop Martin Riggs - not as mentally-deranged as in early drafts (he used a rocket launcher on one guy!)  Some ideas were inevitable: Alec Baldwin, Michael Biehn (shootingAliens), Jeff Bridges, Michael Douglas, Harrison Ford, Richard Gere, Al Pacino, Sean Penn, William Petersen, Dennis Quaid, Christopher Reeve, Kurt Russell, Charlie Sheen, Sylvester Stallone, John Travolta, Bruce Willis. Some were inspired: ,Bryan Brown, Nicolas Cage, Willem Dafoe, Jeff Goldblum (he inherited Gibson’s role in The Fly), William Hurt (too dark for Warner Bros), Michael Keaton, Michael Madsen, Liam Neeson, Eric Roberts. Some were insipid: Jim Belushi, Pierce Brosnan, Kevin Costner, Kevin Kline, Stephen Lang, Michael Nouri (he joined another  \cop duo in The Hidden), Patrick Swayze. Plus TV cops  Don  Johnson, Tom Selleck… three foreign LA cops:  Austrian Arnold Schwarzenegger, Dutch Rutger Hauer and French Christophe(r) Lambert. And the inevitable (Aussie) outsider Richard Norton.

  7. Mickey Rourke, Barfly, 1986.
    "I'm not too young to do it!"  Sean wanted Dennis Hopper, a fellow Bukowski fan, to direct.  Hopper regarded Penn as "the best young actor in  films today" but told him:  "Forget it!  You'll never get  the  rights away from Barbet Schroeder." And he couldn't!"  Although Dennis once told Schroeder -  loudly - at Ma Maison that documentaries didn't make him qualified to direct movies.  Dennis directed Sean in Colours, 1988; vice-versa for The Indian Runner, 1991. And Penn dedicated his directed second film, The Crossing Guard,  1995, to Bukowski.

  8. Bruce Willis, Blind Date, 1987.      Due as first film for Mr and Mrs Madonna when she called the shots, refusing all six of Tri-Star's suggestions. They made the abysmal Shanghai Surprise, instead.   What were they thinking!
  9. Michael Keaton, Batman, 1988.
  10. Alex Winter,Bill & Ted’s Excellent Adventure, 1988.  Producer Scott Kroopf ran into an Italian brick wall when trying to interest iconic producer Dino DeLaurentiis in the project. "He didn't understand what dudes were until someone said: guys who had big dicks. 'Oh, great, now I get it.'" director Stephen Herek whittled down 200-300 actors to 24 for the time-travellers meeting Beethoven, Billy The Kid, Freud, Lincoln, Napoleon, Socrates.  “Everyone was auditioning for both roles,” Reeves told Hollywood Reporter 30 years later.  At one time it looked as if the guys would be Brendan Fraser and Pauly Shore (future Encino Man co-stars in 1991). Except thescript’s skinny teenagers became more cool when Winter, 21, and Reeves, 22, blew away all other hopefuls – when testing for each other’s role.  Also up for Bill S. Preston, Esq,were Sean Penn and River Phoenix.

  11. Tom Cruise, Born on the Fourth of July,  1989.
  12. Whoopi Goldberg, Homer and Eddie, 1989.      Originally, a road movie about two guys (Robin Williams-Jim Belushi or Richard Pryor-Penn), until Russian film-maker Andrei Konchalovsky had his "crazy idea" about using Whoopi -   and that ruined his cruel climax.   "Whoopi   is incapable of real violence to another person -   and I needed that."
  13. Patrick Bergin, Mountains of the Moon, 1989.    For his saga of the Nile source seekers, Burton and Speke, director Bob Rafelson spent seven years trying to raise the budget from Italian tele-tycoon Silvio Berlsuconi EMI, Hemdale, Rizzoli, the Royal Geographic Society, Warners, even lowly Cannon (demanding   locations in South Africa where it had frozen funds).   And Penn -   "a New York street midget," said producer Daniel Melnick, "as Sir Richard Burton!"
  14. Adam Baldwin, Next of Kin, 1989. Penn, Alec Baldwin (no kin to Adam), Robert De Niro, Michael Keaton, Ray Liotta, John Malkovich, Jack Nicholson, Ron Perlman, Tim Robbins were seen for mobster Joey Rossellini in the hillbillies v the Mafia re-run of the same UK director John Irvin’s tons better Raw Deal, 1985.
  15. John Heard, Home Alone, 1990.    For the zero roles of Macauley Culkin’s forgetful parents (in a film written for and duly stolen by him), an astonishing 66 stars were considered - including 32 later seen for the hot lovers in Basic Instinct:Kim Basinger, Stockard Channing, Glenn Close, Kevin Costner, Jamie Lee Curtis, Michael Douglas, Carrie Fisher, Harrison Ford, Mel Gibson, Jodie Foster, Linda Hamilton, Daryl Hannah, Marilu Henner, Anjelica Huston, Helen Hunt, Holly Hunter, Diane Keaton, Jessica Lange, Christopher Lloyd, Jack Nicholson, Sean Penn, Michelle Pfeiffer, Annie Potts, Kelly Preston, Dennis Quaid, Meg Ryan, Martin Sheen, Sylvester Stallone, Sharon Stone, John Travolta.   Other potential Pops were Dan Aykroyd, Jim Belushi, Chevy Chase, Jeff Daniels, Tony Danza, John Goodman, Charles Grodin, Tom Hanks, Robert Hays, Steve Martin, Rick Moranis, Bill Murray, Ed O’Neill, John Ritter, Arnold Schwarzenegger, Tom Skerritt, Robin Williams… and the inevitable unknowns: Broadway’s Mark Linn-Baker, Canadian musicians-comics  Alan Thicke ("the affordable William Shatner") and Dave Thomas.
  16. Brad Pitt, Thelma & Louise, 1990.
  17. Viggo Mortensen, The Indian Runner, 1991.     "I'd like to make a movie out of it someday," Penn told Bruce Springsteen about his song of mismatched brothers. Penn saw himself as the angry, 'Nam vet with KILL and FUCK tattooed on his knuckles, and Robert De Niro as   his   cop brother - before   going all out as (an excellent) director of Mortensen and David Morse.
  18. Michael Douglas, Basic Instinct, 1991.
  19. Tim Roth, Heart of Darkness, 1993.      Austrian director Robert  Dornhelm's preparation for Sean   and Mickey Rourke (as Kurtz), evaporated into Nicolas Roeg’s tele-movie with Roth and John Malkovich.
  20. John Travolta, Pulp Fiction, 1993.  

  21. Bruce Willis, Pulp Fiction, 1993.
  22. Christopher Walken, Pulp Fiction, 1993. 
  23. Tom Cruise, Jerry Maguire, 1996.    Super-Tom One, Hanks, was into his helming debut, The Thing That You Do, 1996. Super-Tom Two, Cruise, said: “I may not be right for this but let me just read for you.” And Super-Tom-One added: “It couldn’t have been anyone but Cruise.” Except auteur Cameron Crowe had also considered Tim Allen (briefly, thankfully), Alec Baldwin, Edward Burns (who reccommended his latest co-star, Connie Britton, for Dorothy; they both came second), Johnny Depp, John Travolta, Bruce Willis. Plus Penn, from Crowe’s first script, Fast Times at Ridgemont High, 1981,
  24. Antonio Banderas,   Evita, 1996.    Madonna's obvious choice for Che Guevera, the first time the musical   was offered to her... years before The Big Split.
  25. Jude Law, Gattaca, 1997.     Other commitments barred him joining Ethan Hawke and Uma Thurman in the sf tale by The Truman Show scenarist, Kiwi Andrew Niccol.
  26. Mickey Rourke, The Rainmaker, 1997.    When director Francis Coppola calls, not everyone comes running. Not anymore.
  27. Alfred Molina, 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”) neededa drug dealer called role of Rahad Jackson.  Penn and John Turturro passed and Molina, being British, could tackle anything!
  28. Jim Carrey, Man on the Moon, 1999.    Czech film-maker Milos Forman also ran through other   possible Andy Kaufmans including Nic Cage, John Cusack, Edward Norton, Kevin Spacey.
  29. Edward Norton, Fight Club, 1999.       Both Penn and Matt Damon were up for TheNarrator.But after shedding Man on the Moon, Runaway Jury, The Talented Mr Ripley, it was Norton prepping with boxing, taekwondo, grappling - and soap- making - for what Chicago critic Roger Ebert called “the most frankly and cheerfully fascist big-star movie since Death Wish, a celebration of violence... masquerading as philosophy.”  Fox Daddy Rupert Murdoch, the great movie know-all, hated it and his studio chief Bill Mechanic wasrapidly dumped.
  30. Joaquin Phoenix, The Yards, 2000. Penn's interest led to a reading of James Gray's second script with Robert De Niro. Neither one made the movie.

  31. Heath Ledger, Monster's Ball, 2001.      Sean was courted to be   Robert De Niro’s son in  the much shelved project - about three generations of prison warders, racists every one.
  32. Sam Rockwell, Confessions of a Dangerous Mind, 2002.      Ditto. Directors switched from Bryan Singer to (superbly) George Clooney, so did the man playing Chuck Barris, TV star and CIAssassin.   Or, so he said.
  33. Ralph Fiennes, Red Dragon, 2002.      Maybe Sean discovered that Francis Dolarhyde's back tattoo would take eight hours to apply. Also considered: Paul Bettany, Nic Cage, Jeremy Piven.
  34. Phillip Seymour Hoffman, Punch-Drunk Love, 2002.     Pulled out   of what   proved Paul Thomas   Anderson's first glitch.
  35. Aidan Quinn, Stolen Summer, 2002.       Penn passed in order to make I Am Sam... and win an Oscar nod.
  36. Jeff Daniels, Blood Work, 2002. Maybe next time, said Clint Eastwood. And, sure enough, Penn was free for Mystic River, the following year - and won his first Oscar!
  37. Johnny Depp, Once Upon A Time In Mexico, 2003.      Agent Sands was always shifting... between Sean,  Nicolas Cage, George Clooney,. Kurt Russell, Bruce Willis. Johnny enjoyed it so much he had no wish to leave after his nine days (mostly improvised)   So, Robert Rodriguez made him the priest talking to Antonio Banderas in the church.
  38. Cillian Murphy, Red Eye, 2004.    Scenarist Carl Ellswsorth’s airplane ethriller was penned for the Penns - Sean and wife Robin Wright.  Except they were no longer the Penns. (Again).
  39. Jodie Foster, Flightplan, 2005.        Revenge!   Jodie took  over what was Penn's, just as he had taken what had been hers in  The Game, 1997.
  40. Matt Dillon, Factotum, 2005.     First choice for Henry Chinaski,  fictional alter-ego of Penn pal Charles Bukowski...

  41. Toby Jones, Infamous, 2006.      Sean missed playing Bukowski twice, and was beaten to the second consecutive film about Truman Capote writing In Cold Blood.   Penn   had also tried to play Irish writer Brenan Behan in   1999, dropping out   after fat man make-up   tests.
  42. Michael C Hall, Dexter, TV, 2006-2013.      Everyone from John Cusack to Jake Gyllenhaaal -andquite stupidly, Penn, Tom Cruise, Ben Stiller! - were listed for TV’s most unlikely hero. Dexter Morgan wasthe Miami PD’s blood-splatter expert moonlighting as a serial killer... of other killers.
  43. Heath Ledger, The Dark Knight, 2007.
  44. Keanu Reves, Street Kings, 2007.    James Ellroy writes his first  script - and nobody wanted to back it. As suits argued, directors changed from  from David Fincher and Spike Lee to Oliver Stone… and even a talented Belgian I know, Erik Van Looy. Ultimately, David Ayer got the gig - and budget. But lost Penn  and Erik made the much better Loft. 
  45. Jackie Earle Haley, Watchmen, 2008.   Not so much “Who watches the watchmen?” as Juvenal asked, but who them playeth? In the 20 years it took to film Alan Moore’s DComic-book, directors came and went - Darren Aronofsky, Michael Bay, Tim Burton, Terry Gilliam, Paul Greengrass. So did their choices for Walter Kovacs aka Rorschach, the masked vigilante: Penn, Daniel Craig, John Hurt, Doug Hutchinson, Simon Pegg, Robin Williams and the prerequisite outsider, Richard Hansard, more known for music than acting (three credits in 18 years).
  46. Christophe Waltz, Water For Elephants, 2010.  One Oscar-winner (Inglourious Basterds, 2010) substitutes another (Milk, 2009) as the twisted animal trainer in a Great Depression era circus. “There's something endearingly old-fashioned,” said Chicago critic Roger Ebert, “about a love story involving a beautiful bareback rider and a kid who runs off to join the circus.” Except it was Waltz’s circus owner who stole the entire movie.
  47. Jared Harris, Sherlock Holmes: A Game of Shows, 2010.      Also in the mix to be Moriarty: Javier Bardem, Gary Oldman, Brad Pitt.
  48. François Arnaud, The Borgias, TV, 2010.      The Italian Caligula director Tinto Brass told me he offered Cesare Borgia to Penn ... long before Irish director Neil Jordan got his filmoff the ground- as a TVseries.
  49. Sean Hayes, The Three Stooges, 2011.      The double-Oscar winner was a shock choice for the simpleton Larry Fine - but he was in, out, and back in again for awhile while his martrage to Robin Wright disintergrated.Penn’s partner were to be Jim Carrey and Benicio Del Torro as Curly and Moe.’Twas obvious from the get-go that this idea was a loser. The Farrellys brothers may love and adore them (hencetheirown un-subtle comedies like Dumb and Dumber) but there are just not that many fans of the Stooges - and their slap-happy boinks, pokes, slaps, nyuk-nyuks, nyaaahhhs - in one US township, let alone the world.
  50. John Goodman, The Hangover Part III, 20012.   The Wolf Pack (Bradley Cooper, Ed Helms and Zach Galifianakis) is back.  Penn - and  Robert Downey Jr  - topped their list for the gangster on their  joint asses because of a missing $42m in gold which… well, you know about MacGuffins! 

  51. Samuel L Jackson, RoboCop, 2013.  Passed - easily - on the jingoistic talk show host checking on whether Americans are  robophobic. They must be after such a weak reboot. New York Times critic Manohla Dargos suggested  Sam  was “tapped for duties so that he can deliver a bleeped Tarantino-esque obscenity.”
  52. Russell  Crowe, Man of Steel, 2013.
  53. Edward Norton, Birdman, 2013.     Decisions, decisions…  A washed-up actor for the Mexican Babel  auteur Alejandro González Iñárritu or a spy in The Gunman for French Taken/Transporteur director Pierre Morel.  Surprise, surprises, Penn chose Spain and butting heads with Javier Bardem,  Idris Elba and Ray Winstone(Still, just making the thriller helped win him a French Cesar Award for his career!).\
  54. Tom Hardy, The Revenenant, 2015.   Hardy gave up Rick Flagg in Suicide Squad to be A new 1820s frontier foe for a vengeful Leonardo DiCaprio… when Sean Penn dropped out due to his over-scheduled diary.
  55. Bradley Cooper, A Star Is Born2017.
  56. Charlie Hunnam,Triple Frontier, 2019.  Five buddies take down a South American drug lord. But whichmagnificent 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.

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