I don't think it's possible to cite a single movie as "the last classic Hollywood type movie" where its focus was entertainment and had movie magic feel to it, but I do think you could make a general list.
Some I'd throw out there for me are Mask of Zorro (1998), the Transporter (2002), the first two Harry Potter films.
What about you guy's. What's your personal list of movies that were sort of the last of that era where movies felt like movies and had something special to them?
I can narrow it to an era rather than any specific movie, because half of everything that released in 1999 was great.
Then 2000 had even better films, some of the best ever made. Gladiator, Patriot, The Boondock Saints, some really enjoyable ones like Pitch Black and Oh Brother Where Art Thou?, but much of the rest were forgettable.
The peak film for me was the LoTR movies. As easily as I can critique every last detail that was off from the books, they are still epic and as close to the book in tone, style and content as any book conversion ever has been. And pedowood has produced nothing of equivalence since, and there is still absolutely nothing else like marathoning them on a big screen
After that, there were still good movies, but there was a steady decrease in both peak quality and overall quantity of "good" films each year.
While I did like the early superhero resurgence, purely for entertainment value, they certainly weren't on the same par as "good movies" and the best of them were actually released quite far apart. GOTG still sits in my personal top ten list, but purely because it's fun and visually entertaining, not because it's any Shakespearian contender.
I've tried many times to get into the LOTR movies. I go "surely THIS time I'll see what everyone else sees in them".
I just don't get it.
I like Fantasy movies, same as any genre if it's good, but LOTR's appeal alludes me.
Try watching them stoned. A good A/V setup is required too. It just isn't the same from a small screen.