What Movie? And what was she doing? Out in 1967

in Cool Hand Luke

Here’s another one somewhat similar

Who said “He’s in the car?” Who was “in” the car? Why? What movie?

2...Letters From Iwo Jima?

But, I think the 2nd one is Paint Your Wagon. That movie was a financial disaster.
Not Eastwood's fault, though. He was in it but had nothing to do with the production.

I still recall "Wand'rin' Star" being a radio hit in Denver. I just looked into it, and was surprised to see it was released as a 45, b/w "I Talk to the Trees."

It didn't lose money, but it grossed $30 million in a budget of $21 million.
But, distribution costs were high; the long running time eliminated 2nd views; it was a musical when younger audiences had little attraction to musicals; and that $30 million took nearly 4 years to accumulate.
After it's movie run, residuals were pitiful as TV stations didn't think enough of it to tie up 4 hours of airtime.
It made the studio about 3% after fully absorbed cost.
Not a turkey like Ishtar, but pretty bad.

If not, I'll see if I can kick-start my brain.

what color is John Milner's (Paul LeMat) hotrod?

A cross between piss yellow and...

well done Mad_Dem_X!

most nights and had conducted climbing expeditions to the top of the local Holiday Inn sign.
One actor set fire to George Lucas' motel room.
Another night, Le Mat threw Richard Dreyfuss into a swimming pool, gashing Dreyfuss' forehead on the day before he was due to have his close-ups filmed. (Wikipedia)

Bonus points for coming up with both characters and actors.

I Got You Babe

(Martin Sheen ended up playing Capt. Willard)

Yes, a guess!

Besides Steve McQueen, who was Coppola's first choice, Al Pacino also turned down the role of Willard.

Steve McQueen was Coppola's first choice to play Willard, but he didn't want to leave America for three weeks, and Coppola was unwilling to pay his $3 million fee.

for casting. In Butch & Sundance he wanted to play Sundance and wanted the film credits as "The Sundance Kid and Butch Cassidy". The studio said no, McQueen walked. (supposedly)

Before there was NC-17 rating

Goodfellas to eliminate some scenes to avoid a NC-17 rating.

Sean Penn, Alec Baldwin, Tom Cruise and Val Kilmer were all considered. The role ended up going to a relative newcomer, who was it?