The cool cities are those where you can do very expensive things for very little money. London and Barcelona are two of them, and to some extent I think Berkeley-SF-BayArea (the other place I've lived for some time) is too.
For instance, in Barcelona you can go and watch, like I did the other day, Notorius (by Alfred HitchCock) at the cinema for 66 cents. It's not only that it's ridiculously cheap but, where can you watch Notorius at the cinema nowadays?
Then, in London, they have this very nice thing called "stand by tickets" for the theatre. The thing is that, if you wanna watch a theatre play or a musical but don't have 30 or even 50 quids (80 euros) to spend, then you can always go there and wait till 5 minutes before the play starts. Then, you might get very cheap tickets at the theatre's box office. Or, as it happened to me once, you might find a lady who bought 20 tickets for a groups of tourists, and then the tourists didn't show up. She sold me two first row tickets for "The Woman in Black" for only 12 quid! Just the money we had in our pockets. And there you had us, first row tickets and no money in our pockets. This things make cities great.