- Annabeth Gish, 1985. At 15, she lost her first movie) but her test had agents chasing her. “I’m probably one of the few kids ever to get signed by a top agency without having any acting experience - and who then left their agency a year later. I intend to be around a long time.” Spoken like a true God-daughter of LSD ikon Timothy Leary!
- Julia Roberts, Steel Magnolias, 1989. Bette Davis tried to film the off-Broadway play with Katharine Hepburn and Elizabeth Taylor. Producer Ray Stark decided to go younger. “I was crazy about Winona,” said director Herbert Ross, “but she was just too young.” She was 17, Roberts was 21.
- Emily Lloyd, In Country, 1989. Got her (short-lived) revenge by upending Emily in Mermaids. Neither film swam.
- Judith Hoag, Teenage Mutant Ninja Turtles, 1990. For the first live-action Turtle trot, the innovative director of music videos Steve Barron saw many a potential April O’Neill: Ryder, Jennifer Beals, Lorraine Bracco, Sandra Bullock, Melanie Griffith, Anna Kendrick, Nicole Kidman, Brooke Shields, Marisa Tomei, Sean Young. TMNT legend states the winning Hoag lost the sequels because she had complained so much the violence - and the six-day shooting schedule.
- Julia Roberts, Pretty Woman, 1989.
- Sofia Coppola, The Godfather: Part III, 1991.
- Juliette Lewis, Cape Fear, 1991. Among the many - the very many - Christina Applegate, Drew Barrymore, Jennifer Connelly, Shannen Doherty, Nicole Eggeret, Bridget Fonda, Jodie Foster, Helen Hunt, Nicole Kidman, Diane Lane, Jennifer Jason Leigh, Alyssa Milano, Demi Moore, Sarah Jessica Parker, Molly Ringwald, Meg Ryan, Brooke Shields, Tiffani Thiessen, Reese Witherspoon - considered by Steven Spielberg and, later, Martin Scorsese for the teen daughter of Nick Nolte and Jessica Lange: Danielle Bowden. (Nicole in the 1962 original). Some found it too sexy and, indeed, few could have equalled the on-heat musk of Juliette’s totally improvised - and one take - seduction scene with Robert De Niro.
- Mila Jovocich, Chaplin, 1992. Originally selected to be Mildred Harris - a teenage Mrs. Charlie - but she had been rewarded by Francis Coppola for telling him about Jim Hart’s Dracula script. Francey made her Elisabetta, the Count’s long dead bride born again (?) as Keanu Reeves’ fiancee, Mina Murray.
- Bridget Fonda, Point Of No Return, 1993. She was keen. Warners was keen. Luc Besson was not. He’d created Nikita in France (and for his wife, Anne Parillaud). He didn’t feel like repeating the exercise in Hollywood. With a stranger.
- Rosie Perez, Fearless, 1993. “Her competition for the role was Winona!” declared Perez’ proud manager. “She’s this black Puerto Rican girl from Brooklyn - and she got the role.”
- Sandra Bullock, Speed, 1993. Although sharing the heroics and the driving of the bus-bomb with Keanu Reeves, most girls saw it as The Guy’s film. An amazing 36 refused to be Annie: Winona, Rosanna Arquette, Kim Basinger, Halle Berry, Glenn Close (!), Geena Davis, Cameron Diaz, Carrie Fisher, Bridget Fonda, Jodie Foster, Melanie Griffith, Daryl Hannah, Barbara Hershey, Anjelica Huston, Diane Lane, Jessica Lange, Jennifer Jason Leigh, Kay Lenz, Alyssa Milano, Demi Moore, Tatum O’Neal, Sarah Jessica Parker, Michelle Pfeiffer, Julia Roberts, Meg Ryan, Jane Seymour, Ally Sheedy, Brooke Shields, Meryl Streep (!), Emma Thompson (!), Meg Tilly, Marisa Tomei, Kathleen Turner, Sigourney Weaver and Debra Winger.
- Jennifer Jason Leigh, The Hudsucker Proxy, 1993. "I've landed every role I ever wanted except for Hudsucker. Ellen Barkin, Bridget Fonda and Nicole Kidman also lost Amy in the 1994 Cannes festival opener from the Coen brothers. Not a patch on their following year’s entry (and winner of four Oscars), Fargo.
- Rebecca De Mornay, The Three Musketeers, 1993. Ryder had been an early thought for the Countess D’Winter opposite Chris O’Donnell (D’Artagnan), Charlie Sheen (Aramis), Kiefer Sutherland (Athos), Oliver Platt (Porthos). The Disney frolic was mainly shot in Perchtoldsdorf, Austria, where Rebecca attended high school and college.
- Julia Roberts, Mary Reilly, 1995. Tim Burton went back to his Beetlejuice and Edward Scissorhands girl for Dr Jekyll’s parlour maid… before passing the project to UK director Stephen Frears
- Julia Ormond, Sabrina, 1995. She felt she could not match Audrey Hepburn’s original. And that the role was marked by sexism. Next? Juliette Binoche, dancer Darcy Bissell, Sandra Bullock, Julie Delpy, Cameron Diaz, Demi Moore, Gwyneth Paltrow, Robin Wright, Catherine Zeta-Jones. All better than Ormond. So it blows.
- Annabeth Gish, Beautiful Girls, 1995. Another one that got away...
- Jeaneane Garofalo, The Truth About Cats and Dogs, 1995. Winona preferred to be The Older Woman in Boys, 1996. Older, that was, compared to co-star Lukas Haas.
- Renée Zellweger, Jerry Maguire, 1996. The first idea, Tom Hanks and Winona, must have looked like father/daughter. She then tested with Cruise: they must have looked downright incestuous
- Julia Roberts, Conspiracy Theory, 1997. Although faxing-pals since Maverick, Jodie Foster still had to turn down working with Mel Gibson again due to Contact. Ryder passed and Roberts went conspiritorial with Gibson.
- Jennifer Aniston, The Object of My Affection, 1997. First Julia Roberts, then Ryder and Sarah Jessica Parker passed on the pregnant friend of a gay Paul Rudd in what Chicago’s ace critic Roger Ebert dubbed a seriocom - “the worst kind of sitcom - a serious one.”
- Gwyneth Paltrow, Shakespeare in Love, 1998. When Julia Roberts and Daniel Day-Lewis didn’t make it happen in 1994, the project became - for a wee while - Winona and Kenneth Branagh.
- Demi Moore, Passion in Mind, 1998. A woman is living parallel lives: a book editor in New York, a mother in France. Michelle Pfeiffer tired of it - after ten years! - and Demi beat the rest to a deal.
- Helena Bonham Carter, Fight Club, 1999. Fox wanted a name for Marla Singer, hanging out at support groups because "it's cheaper than a movie, and there's free coffee.” Like Winona, Sarah Michelle Gellar, Courtney Love or Reese Witherspoon. UK director David Fincher wanted HBC or Anna Friel. The studio voted Reese. Reese veoted that plan. Fincher got his way. Fox Daddy Rupert Murdoch hated the movie and studio chief Bill Mechanic was rapidly dumped.
- Christiana Ricci, Sleepy Hollow, 1999. The role, Katrina Anne Van Tassel, historic kinfolk of of another of the cast, Casper Van Dien.
- Kirsten Dunst, Spider-Man, 2001.
Anna Vareschi, The Brown Bunny, 2002.
“I was never going to put Winona Ryder in a significant role...!” Vincent Gallo made it clear at the 2003 Cannes festival. She was never up for Chloe Sevigny’s role - and the the shock fellatio scene. Gallowanted her for gas stationattendant Violet (all the film’s women were named for flowers) that Kirsten Dunst had agreed tuntil her agent heard about it.“Right after the Kirsten debacle, I just happened to get one of those Winona calls.... She calls me every five months. [Goes into an impersonation].‘Hi, I love you...’ And I thought, Oh wow, she’s inthe papers, I know she’s done it [shoplifting]Iknow she’s going to jail. This will be good [publicity] for the film!‘Hey, Noney, yeah, how’redoin’?Would you come to New Hampshire tonight and be in this film?’‘Oh, I’d do anything for you’... on and on and on. And this is really what happened...It was very open, she didn’t call her agent. With all the publicity surrounding her at the time, it was actually courageous and fantastic that she actually flew into Boston and showed up on the set. The only problem was, unlike Chloe, she didn’t trust me. She ball-busted me about the wardrobe, about the make-up. At 9m, she was sleeping with a mask on and ear-plugs in and no one could get her out of the room. She had, let’s say, some tablets that seemed to have impact upon her behaviour. So I said to my crew - of two... “Listen guys, we’re gonna fire Winona Ryder!”And we’re going to go into townand the first girl we seeover 12 and under 100 is gonna bein the movie.And I swear to the Bible... we walk into the main street of this town, I see someone with long hair, a sort of boyish body, could bea boy, could bea girl. It’s a girl!I say: ‘Excuse me, Miss, I’m making a movie...’ Aha! And 20 minutes later, we’re inthe van - the kissing scene. Twenty minutes later! I kiss her and I touch her and she’s traumatised. Next day, when we filmed inthe gas station, she was sarcastic, nasty, horrible to me... had to readjust the scene, I think she’s fantastic and beautiful.That’s what happened.”
- Ashley Judd, Olympus Has Fallen, 2002. Surprisingly, Ryder was was the studio's first choice for the First Lady, wife of Aaron Eckhart’s President. Instead, it became Judd’s fourth of five movies with Morgan Freeman. (Olympus is Secret Service code for the White House).
- Naomi Watts, Le Divorce, France-US, 2003. She withdrew from the French project of Indian producer Ismail Merchant and American director James Ivory
- Nicole Kidman, Bewitched, 2004. Who wants to play wriggly-nosed Samantha? Me, me, chorused... Jennifer Aniston, Kim Basinger, Cameron Diaz, Heather Graham (who would have been quirkily great), Angerlina Jolie, Lisa Kudrow (perfect!), Tatum O'Neal (not so much), Gwyneth Paltrow Michelle Pfeiffer, Julia Roberts, Meg Ryan, Alicia Silverstone, Hilary Swank, Naomi Watts. Among 35 possibles. Over the years.
- Radha Mitchell, Melinda and Melinda, 2004. Woody Allen was going the (cheap) rehab route with Winona and Robert Downey Jr. And then dumped both! He needed a winner more than a Winona after his previous, $18m Anything Else grossed only$3.8min three weeks… He craved Winona but no company would insure her after her infamous shoplifting arrest. (Nor, he said, for Downey).Naomi Watts was too busy.Instead of looking further, Woody allowed the film to fail by selecting the Australian he’d enjoyed in Ten Tiny Love Stories, 2000 - she was not able to carry a movie. Or, indeed two, considering her dual role. Woody learned two lessons; auditions are also known as tests and not every Aussie actress is Judy Davis. (She made five Woody movies). Ryder and Downey had worked together – in Richard Linklater's animated take on Philip K Dick's A Scanner Darkly in 2003, Ryder and Downey finally did get to work together – along with Keanu Reeves, Ryder's Dracula co-star - in Richard Linklater's animated take on Philip K Dick's A Scanner Darkly.in 2003,
- Molly Parker, The Wicker Man, 2005. Winona was asked. Winona refused. Wise girl. It was a t terrible re-make of a classic UK horror film.
- Anna Faris, Smiley Face, 2007. Winona was the lead when it and the film were called Mary Warner.
- Charlize Theron, Snow White and the Huntsman, 2011. When Angelina Jolie rejected the first of two revisionist Ms Whites that year, Theron quit Clint Eastwood’s J Edgar to grab the evil Queen Ravenna. And still found time for Ridley Scott’s Prometheus opposite Michael Fassbender, once listed for the Huntsman.
- Olivia Wilde, The Incredible Burt Wonderstone, 2012. Jessica Biel, Judy Greer, Michelle Monaghan, Sarah Silverman were also shortlisted for the rose between two thorny magicians in their old-fashioned Vegas act.
- Zooey Deschanel, Eulogy, 2013. Attached, once upon a time, to then funereal black comedy. Just not when Zooey, Hank Azaria, Ray Romano, Piper Laurie, Debra Winger were the dysfunctionals attending their patriarch Rip Torn’s funeral.