Prohibition didn't end because people missed the taste of alcohol; it was because people kept on drinking (and the illicit nature brought with it the trappings of criminality - corruption, violence, and murder).
Gay marriage bans were hard to "ignore" because it requires cooperation with the government, but anti-sodomy laws were generally ignored until it became comical they were still on the books.
And in general, these kinds of things are the way change happens. The first people at my work switched to git on their own discretion and against the "rules", but it caught on and was productive/popular enough that it's now common practice and no managers ruffle their feathers at the thought.
The phrase is something like - "It's better to ask for forgiveness than for permission". That's because it's easy to say no when asked for permission ("The rules are there for a reason! Tradition!"); if someone has to think about why what you did was wrong, they may come to the conclusion that you were right.
Though the only comparison I think fits the most with Uber is prohibition (since alcohol can be considered as a luxury, while marriage is a legal right). Don't forget though, with prohibition there was a complex underground bootlegging market funding organized crime. Also there's the whole Great Depression thing which put the whole country in need of additional revenue streams...
When you get to that point, it's obvious that the regulation is backwards, and it's nobody but taxi drivers that made it this way: they got licenses for free, then fought for their right to transfer them for money, then they fought to limit new licensing. Basically they lobbied for free money and screwing customers.
Not disagreeing here. However, fines are put in place as a deterrent. In this instance, their purpose is a punishment for breaking a law. Uber is treating them like a tax and the government appears to disagree with that interpretation. If this were a case of a chemical company continuing to improperly dispose of waste, i'm sure at some point you'd want the government to step in over continued violations (i.e., stop them when they are clearly not acting in 'good faith').
Do you honestly think Uber can be compared to the civil rights movement?
Second, you would be wrong to trivialize the importance of expanding the offering in cabs. Uber will go into neighborhood where Taxis don't, they can also be substantially cheaper depending on the city and the specifics. Having access to a ride late at night can mean the difference between being raped or not raped for many people living in high crime neighborhood. In addition, Uber provides a livelihood for a large number of drivers. The taxis that it compete are generally renting their license from a large company who is collecting the monopoly rent.
This sounds like an American problem. Part of being a licensed taxi driver in Europe is that you can't refuse service in certain parts of town. Same for taxi hours. I have never not gotten a taxi by phone in Vienna.