Remember that they've been making films in Hollywood for over a century (the first short to be made there was in 1910 and the first feature in 1914) and it's a very incestuous industry, so you have a smallish number of people floating back and forth between multiple film productions and sharing their techniques with each other, and the fundamentals of film production haven't really changed all that much.
One upside of this is that you can very quickly tell whether someone knows what they're doing or not - scripts are formatted in a certain very particular way, there's a lot of set jargon and so on. As far as software goes, there's plenty of room for innovation (which I'd be happy to discuss) but you have to be 100% backward compatible with existing practices. Nobody wants to waste time learning something that fall short and result in them getting yelled at, fired, and talked about negatively, so people are pretty conservative.
Of course, Hollywood isn't the only industry like that. Most are, in my observation. One of the biggest challenges in B2B software is overcoming the incumbent, no matter how bad they are.
To be fair, I haven't seen a competitor to MM that blew me away, and MM has improved jussssssst enough to keep people from running away. The ipad version of Scheduling is certainly a step in the right direction.
It's an interesting situation, where it looks like there's space for a competitor, but there really isn't.