- 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...
- 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.
- Judge Reinhold, Fast Times At Ridgemont High, 1982. Penn read for Brad Hamilton and won the lead Jeff Spicoli - and was so into character that he only answered as Spicoli and his dressingroom door was labeled Spicoli. Also in the Brad mix: Matthew Broderick and Ralph Macchio. Spicoli was the surfer dude who ordered pizza delivered direct to the classroom.
- Tom Cruise, Top Gun, 1985. Refused the US Navy pilot ace called Maverick So did:Matthew Broderick, Nicolas Cage, John Cusack, Emilio Estevez, Michael J Fox, Tom Hanks, Matthew Modine, Patrick Swayze.
- 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.
- 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!
- Tom Cruise, Born on the Fourth of July, 1989.
- 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."
- 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!"
- John Heard, Home Alone, 1990. An astonishing 37 stars (Harrison Ford, Jack Nicholson, Jessica Lange, Michelle Pfeiffer, etc) were considered for the forgetful parents - nothing roles in a film written for and duly stolen by the stranded kid, Macauley Culkin.
- Brad Pitt, Thelma & Louise, 1990.
- 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.
- Michael Douglas, Basic Instinct, 1991.
- 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.
- John Travolta, Pulp Fiction, 1993.
- Bruce Willis, Pulp Fiction, 1993.
- Christopher Walken, Pulp Fiction, 1993.
- 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.
- 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.
- Mickey Rourke, The Rainmaker, 1997. When director Francis Coppola calls, not everyone comes running. Not anymore.
- 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.
- 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.
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.
- 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.
- 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.
- 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.
- Phillip Seymour Hoffman, Punch-Drunk Love, 2002. Pulled out of what proved Paul Thomas Anderson's first glitch.
- Aidan Quinn, Stolen Summer, 2002. Penn passed in order to make I Am Sam... and win an Oscar nod.
- Jeff Daniels, Blood Work, 2002. Maybe next time, said Clint Eastwood. And, sure enough, Penn was free for Mystic River, the following year - and wonhis first Oscar!
- 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.
- 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).
- 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.
- Matt Dillon, Factotum, 2005. First choice for Henry Chinaski, fictional alter-ego of Penn pal Charles Bukowski...
- 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
- 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’sblood-splatter expert moonlighting as a serial killer... of other killers.
- Heath Ledger, The Dark Knight, 2007.
- 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.
- Jackie Earle Haley, Watchmen, 2008. Not so much “Who watches the watchmen?” as Aristotle 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. Unknown then. And now.
- 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.
- Jared Harris, Sherlock Holmes: A Game of Shows, 2010. Also in the mix to be Moriarty: Javier Bardem, Gary Oldman, Brad Pitt.
- François Arnaud, The Borgias, TV, 2010. The Italian Caligula director Tinto Brass told me he offered Cesare Borgia to Penn ... long beforeIrish director Neil Jordan got his filmoff the ground- as a TVseries.
- 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.
- 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!
- 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.”
- Edward Norton, Birdman, 2013. Decisions, decisions… A washed-up actor for the Mexican Babel auteur Alejandro González Iñárritu… or a spy in The Guman 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!).
- 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.