Basically, Bob NEEDS Mario to be a successful live action movie franchise made by Hollywood both to redeem the failure that was the 1993 movie
Irony: If he'd stop simping for it, people would probably forget all about the 1993 live-action Mario flop, most people have, and the increasing number of people born after it probably aren't even aware it
exists. But Bob's constant demands that society invest money to retroactively correct this ensures people who otherwise didn't know/care will look it up and become aware of it's colossal failure.
Thus ensuring the brand becomes more known for failure than obscure to the point of trivia, thus, less-likely to be resurrected due to the fact that Hollywood investors are risk-averse, and will only reboot POPULAR or at least middling franchises/films, not bombs.
Why do this? Why behave in a way that literally moves your stated goal further into "unlikely"? Ego.
It's not enough that he commit the perfect crime, he, paradoxically, wants the credit for it too. He's a murderer who's managed to kill someone and made it look like an accident, and did such a good job that the coroner wrote it up as "accidental". But, he can't STAND the fact he's not getting credit for all the hard work, he wants the ruling to be "homicide" and then revel in the cops inability to solve it..... It's not enough to win, other's have to publically LOSE to confirm the win.....
Fundamentally, it's not enough that he (and those who share his pathology, just in other areas of culture) be right, or even wrong, but unmolested for it...
It must be IMPOSSIBLE for there to be disagreement before he'll rest. Things must align with his worldview on ALL levels. They must get the recognition that not only did they have all the answers, but here's the PROOF: Everyone who "defied" him and his dogma? They
failed.
As long as one even meager success exists outside Bob's "approved" vision, he cannot enjoy himself, not even for a second.
Hence why these people never know peace.... he's Wile E Coyote... he's gonna GET that Roadrunner even when anyone else can see that the universe is wired in a way that makes it impossible and that if he'd just go get a hamburger like the rest of us, and leave that bird as a "well, I tried, but it wasn't to be" former-ambition he'd be content and fed for the day. Instead of exploded and crushed, again.
The old chestnut about robber barons v ideologues rises again to prove that it was right: Those who desire acquiring for themselves (be it money, power or Funko Pops) may eventually get enough of it to be satisfied. Those who live to deny the same thing to others can never rest for that means the "enemy" gains on you while you sleep....... and Bob's "thing" is to be the King of Pop Culture, not by educating himself on it until he can master it's properties, but, to deny OTHERS the ability to influence it through tearing down what he sees as their "Inferoir" choices (Sonic ) .
Even if he was a successful Warner Brothers exec, whose pitches always hit and hit big, he couldn't enjoy it because somewhere on the internet, someone made an indie film about something OTHER than what Bob likes and it's "like" ratio is high, despite being BAD AND WRONG AND RACIST!!!!!! (because it's not his)
He wouldn't' rest until he CnD'd it into oblivion, even if WB didn't own the property, he'd have lawyers working around the clock to find SOMETHING in it that's juuuuuuuuuust close enough to some obscure copyrighted thing the company did back in 1923 that he can shut it down...... he MUST be the ONLY source of popular entertainment.
Furthermore, his obsession with 1993 Mario liveaction? Well, he's hung up on a point where he sees the timeline as having diverged from it's "true" path and is trying to not just stop society from moving forward from that point, but, going back and "fixing" it.
So not only does he want to control the future pop culture choices of the masses, in true 1984 style he wants to be able to go back and retcon the past so that eventually people will forget they even had the CHOICE of disagreeing. We've always been at war with Eurasia, and Movie Bob has always been right in predicting what the audiences would love!
And since this task is impossible, he's forever gonna be miserable.