Whats the first live action isekai movie ever made? Was discussing with my friends... suddenly got an epiphany ... Its THE MATRIX. Isekai into a digital world, while being helped with level-ups by their operator downloading skill into their brains. Am i wrong?
If you want real isekai, watch the 10 part series The 10th Kingdom https://www.imdb.com/title/tt0207275/?ref_=ttls_li_tt
If we're talking the very first live action isekai, what comes to my mind is The Wizard of Oz, since Alice in Wonderland was animated. Actually...I think it was revealed that Disney did a live action recording for Alice in black and white? I believe I saw it in the special features on the anniversary edition. Maybe that one is first, if it counts. Other titles people have yet to mention are A Kid in King Arthur's Court (based off of the superior Yankee in King Arthur's Court), Warriors of Virtue, the 1988 Narnia series (not the modern movies), Monkeybone (in a sense), Corpse Bride/Coco/The Book of Life, etc, and for a reverse isekai, Enchanted.