Drew Barrymore was cast as Sidney before commitments cut her to four days; Molly Ringwald was Williamson's first choice for Sidney; Brooke Shields for the Courtney Cox reporter; Ben Affleck considered for the Skeet Ulrich part; Breckin Meyer for the Jamie Kennedy part; Reese Witherspoon declined to audition for Sidney; Rebecca Gayhart (as transcribed) for the Rose McGowan part; Freddie Prinze (as transcribed) up for a role
Drew Barrymore was supposed to be Sidney and was locked in, the first to buy in and give the script credibility, but commitments left them four days with her, so she played the opening scene, which is thought to have helped the movie.
It is hard to name another 1996 actress who could have carried the first murder with the same weight; Jennifer Aniston pretending to be eighteen is rejected, while Barrymore was famous yet young, a zeitgeist star.
Neve Campbell was caught at a nice point in Party of Five; in a fantasy draft of 1996 actresses including Aniston, Courtney Cox, Reese Witherspoon and Sarah Michelle Gellar one host would take her top five for a 25-year career, while another never really got it.
Party of Five trained her to do the sad emotions better than anybody, and she is formidable enough that you believe she would win a straight-up fist fight, which is why Drew Barrymore would not have worked as well in the lead.
Gail Weathers getting punched in the face is another good scene for a host who hated Friends as a kid and still counts Ross as the least favorite character, which draws the remark that this is a hot-takey podcast.
Neve Campbell never found a second stage after starring in a hundred-million-dollar movie; she is thought to have gone artsy and precious with the dance movie The Company, and her House of Cards appearance was greeted as a comeback.
Molly Ringwald was the first choice Williamson wrote the movie for; she turned it down as too old at 27, which would have been a disaster as a high school senior, though an aged-up, harder-edged Gail Weathers might have suited her.
Brooke Shields was in the mix for the Courtney Cox reporter role and Ben Affleck was supposedly considered for the Skeet Ulrich part, but this is one of the few movies where no name could be plugged into any role to improve it.
Jamie Kennedy's part is the one that might have been stepped up, yet Breckin Meyer, who was up for it, would not have worked, because the character has to be annoying in the right way.
Reese Witherspoon was wanted to audition for Sidney and wanted no part of it; she would have been good in anything, even Predator, and instead made the roller-coaster movie with Mark Wahlberg and the gnarly Freeway that year, with Cruel Intentions flagged for a future episode.
Rebecca Gayhart (as transcribed) was up for Rose McGowan's part, though nothing like her, and was then put in Scream 2; after 90210 and the Noxzema ads she looked destined to be a massive star, but like Felicity she was hair dependent in a way that fit only 1996.
Freddie Prinze (as transcribed) was remembered from the research as up for one of these roles; he was neck and neck for everything for three years, and gets away with his acting only in high school movies, so Summer Catch and She's All That cut around his throwing and kicking.
Kate Winslet had to do a screen test, watchable online, opposite Jeremy Sisto, Elton from Clueless, who auditioned but probably was not in contention; the major name in contention for Jack Dawson was Matthew McConaughey.
Stephen Dorff is the verified one: a New York Daily News piece headlined 'actor is thankful he didn't get Titanic role' has the Blade co-star saying he wanted a career like Johnny Depp, Sean Penn and Jack Nicholson and an Oscar, which Titanic would have made impossible, and that Leo will always be the guy on the boat.
One host disagrees that Leo is the guy on the boat, since he has been in so many hits and everyone has a favorite Leo, whereas Matt Damon and Ben Affleck are more locked into their 90s work; Sofia Coppola is said to have made Somewhere with Dorff because he never blew up, and Titanic will be in the first line of DiCaprio's obituary, and of Billy Zane's.
Billy Zane has not done much anyone has heard of since, though he has been in three times as many films as Kate Winslet.
Chris O'Donnell, named on Wikipedia for Jack, would have been a great and adorable Jack given his Batman movies and a season-two television arc, but could not have taken the film past a billion dollars; Leo is singular and the chemistry is enduring, though he seems strikingly innocent and little in it.
Rob Lowe was in the mix for Cal and is a great asshole, as in St. Elmo's Fire; pre-West Wing he might not have pulled viewers out of the film, though one host says he would have a little, and the leads mostly had blank or clean reputations at the time, which the hosts think mattered.
