edit: barrkel posts a comment that links and explains the Trademark law around this. search for it and upvote!
https://rodriqueslaw.com/blog/how-use-brands-and-products-fi...
It references some of the existing caselaw. My reading suggests Apple would be very unlikely to succeed in court if they legally challenged a filmmaker for simply giving an iPhone to a villainous character.
>Boss: It looks serious. Those guys are using Macs.
>Technerd: No worries. Macs are second rate systems. A bit slow. A bit inflexible. We'll not have any problems getting control of their systems and out maneuvering the kiddiez.
Bond rapes Pussy Galore and he's such a man that she falls for him and joins his side.
Actual rape.
But you don't need permission to say or use trademarks in a movie. Josie and the Pussycats is a famous example: they used a ton of trademarks to make it look like product placement, where in reality they weren't paid for all of the trademarks they used (nor did any of the named brands complain):
https://en.wikipedia.org/wiki/Josie_and_the_Pussycats_(film)...