Would Speilberg be successful enough to reboot Warner Brother's animation around 1990?
I think Spielberg would have been OK for the most part. 'E.T.' would still have landed with audiences even without ILM's involvement. Without 'Indiana Jones' though he may not have had as much clout initially, but I still think 'The Color Purple' and 'Empire of the Sun' would have gotten made, which solidified his standing with the academy, and even if it wasn't as revolutionary, any version of 'Jurassic Park' he makes is bound to be a crowd pleaser and a box office draw, especially in a market starved for adventurous escapism over the previous decade.
But who knows; in this timeline '1941' could have been a smash hit! Worse movies have certainly made a ton of money when the timing was just right. Also, without the three Indy films; this is probably a timeline in which he actually makes 'Blackhawk', 'Reel to Reel' and '
Night Skies', the latter of which may eliminate 'Gremlins' as a project a few years later (or at least his involvement in it) given the similar tone and subject matter. Similarly I think he still doesn't make '
E.T. II: Nocturnal Fears', both because this and 'Night Skies' seem like they'd be mutually exclusive, and for the same basic reason he didn't follow through with it in reality (it's just a fundamentally bad idea.)
'Hook' may have flopped quite badly though. It was a high risk project and if the VFX industry just wasn't up to realising some of the visuals, it would have really struggled not to collapse under it's own weight.
'A.I. Artificial Intelligence' presents interesting possibilities since he seemed to make it mostly because it was Kubrick's passion project that he never got to finish, therefore this feels like a "come hell or high water" project for him. No telling what the state of VFX would be by the turn of the century, but it's a fair bet the computer technology would still be a decade behind, just now getting into simple photoreal renders, morphs, and digital compositing, so it would have worked, albeit achieved with more traditional methods. Teddy for example would likely have been realised with more traditional puppetry instead of the sophisticated animatronics that just aren't there yet.
Which actually brings us to Stan Winston, who without getting his start on 'Terminator', probably doesn't get hired on for Jurassic Park and this almost certainly not AI either. So many Teddy would be a Jim Henson puppet?
Now that I think about it, A.I. would have to be the potential to be THE blockbuster of the early 2000's since there's no 'Titanic', no 'Matrix', obviously no Star Wars prequels, and it's debatable what happens to the superhero resurgence. Maybe 'Spider-Man' gets made much earlier, maybe 'Blade' has a very different, more campy tone, maybe X-Men doesn't happen at all?
Hell, maybe in this timeline 'Howard the Duck' does astonishingly well and it's TMNT that falls flat?