Also weird to think that both Sean Connery and Brad Pitt passed on playing Morpheus. Either one would have resulted in a vastly different movie.

Speaking of Connery, imagine had he not turned down the role of Gandalf. "You! Shall not! PASH!"

I can't imagine that Burt Reynolds playing Han Solo would have worked out well at all.

How about Frank Sinatra as Dirty Harry? I think he could have pulled it off okay, but I doubt it would have been a franchise and Clint Eastwood would not have had the same career. I think Clint would have been stuck mostly in westerns and probably turn to directing full-time when those dried up. It was supposed to be set in NYC originally too. I think San Francisco was much better, because back then, the country associated it with hippies and "weirdos" (maybe they still do). Audie Murphy was supposed to be offered the role of the Scorpio Killer, but he died in a plane crash. Andrew Robinson did such a great job in that role, I can't imagine anyone else in it, but the idea of having a guy with 240 "confirmed" combat kills playing a serial killer is intriguing.

Supposedly, Sarah Michelle Gellar was offered to star in Clueless before Alicia Silverstone. I think SMG would have done Cher just as well as AS, and not had a big impact on the movie. But if SMG had starred in a breakout hit movie in 1995, would she have signed up to star as Buffy on The WB two year later? I don't think so.

Katie Holmes was the first choice for Buffy, but she turned the offer down. So, likely Buffy the Vampire Slayer would have been played by Charisma Carpenter (with dyed blonde hair).

As a die hard BtVS fan, I can say that having a total sex bomb in her late 20s playing the 16 year old slayer would have resulted in a very different show.

Had Grace Kelly not quit Hollywood which Hitchcock films would she have been in?

I think she would have been his first choice for Vertigo

Even if the movie Clueless would have worked just as well without Alicia Silverstone,I am not sure if it would have been a big hit and had the same cultural impact without her. She was a known entity with youth culture at the time thanks to "The Crush" and the 3 Aerosmith video's she was in being a staple of MTV. Would have been harder to market a summer movie around an unknown at the time actress like SMG,

She may even have been approached to do MARNIE (1964) and might actually have considered a comeback in it, but Prince Rainier wouldn't have gone along with it. That's what I'm remembering. FWIW, here's what IMDB Trivia says:

Totally love Almost Famous but had no idea Brad Pitt was in consideration for the role. Think Crudup did well.

For the reasons you stated, there is no denying that Silverstone had a much higher Q Score with the MTV/teen audience than Gellar. However, it is also worth considering how much the success of Clueless was a matter of it being the right kind of movie at the right time.

Clueless was a movie about teenagers marketed to teenagers, at a time when that really wasn't happening. To some it extent, it was the tip of the spear for all the "set in high school" movies and TV shows that would suddenly start appearing in 1997. It was like there was this under-served demographic waiting for Hollywood to start directing content at it.

No denying that it's almost impossible to imagine anyone being Cher like Silverstone was Cher.

But Gellar is a good actress, and people must have thought she could capably play Cher if they offered her the role first.

I feel like Brad Pitt would have thrown off the balance in the film.

This is a totally superficial take, but part of the movie is Jeff's jealousy over the attention Russell receives. Crudup is better looking that Lee, but not that much better looking. Put Pitt in there, and Jeff "wondering" why Russell gets attention makes him seem like a fucking moron.

More than in consideration. He was cast and learned to play the guitar. But delays hit and he had to drop out for Meet Joe Black.

If you are really interested in the making of the film, I suggest checking out the Origins podcast series he did for the film’s 20th anniversary in 2020, which is an oral history of the making of the film with interviews with pretty much everyone involved (except Pitt and PSH, of course), done by James Andrew Miller who wrote the oral histories of ESPN and SNL — both books I really enjoyed.
https://variety.com/2020/music/news/...ns-1234642300/

If he was like his character in Deliverance, I could see it working. I do wonder if his star power would have kept them from slowly changing Han into a more teddy bear character that he ended up being in Jedi.

I imagine Reynolds wouldn't have stuck around for Jedi, which creates an interesting third movie without Han.

He made two Cannonball Run movies. You don't think he would have agreed to three Star Wars movies?

Well, he was the big star of those movies, and they were made with his friends/lackeys.

The fame of Star Wars and its characters is bigger than any of the actors. Also, so highly technical it would not be a lot of fun. I think Reynold's ego and his desire to enjoy/have control over the production makes him regret being in Star Wars more than Alec Guiness.

Cast Dom DeLuise as Jabba the Hutt and Reynolds would have done RotJ.

I mean, that did in fact happen.

^ I honestly didn’t know that was Dom DeLuise voicing Pizza the Hutt.

If Pacino got the lead in Pretty Woman would I have to reconsider and actually like that movie?

It would have been a far, far different movie, but probably a good one.

No sequels, though.

Toshiro Mifune as Mr. Miyagi. I don't think he'd have the sensitivity or heart of Pat Morita. It would feel more like a straight up revenge film.

Just thought of another one while I was laying in bed awake last night...

John Lennon and Dr. Falken in Wargames.

I'm not sure I'd believe Richard Gere's character hiring a prostitute that looked like Al Pacino.

Marilyn Monroe as Honey Ryder in Dr. No