We have lots of fleeting/meaningless pleasure that is not actually satisfying (we have to keep varying things to keep interested). Was Plato predicting the emptiness of contemporary society and shallowness of popular culture?
Plato’s remedy is austere: the only goal capable of having the stability of unifying a life is pursuit of reason. (Not incompatible with modern conceptions of the good life, for theists or academic-minded people).
Plato offers valid criticism of entertainment and high culture, but he underestimates the value of certain kinds of play. He didn’t see that we play not at things we want to become, but also things we’re afraid of or want to learn about.