I doubt Jobs' thinking out of the box made Apple successful. In fact, I don't believe "thinking outside the box" will do any good in the market. That's what people most of the time repeat without putting some thought into it. Opposite to the typical belief, the market is always conservative and do not accept extremely revolutionary products unless there is already a need for it. Meaning, customers have already tried substitute(s) but it failed them. What Jobs did was understanding those failed experiences and provided a better experience. Take iPod as an example. The market had already experienced Walkman and other mobile music players, but the quality of performance wasn't desirable or there was space for further improvement.
As a matter of fact, the greatest improvement Jobs brought about to the electronics market was not the individual products of iMac, iPod, iPhone, and iPad per se but the total experience a customer can achieve by using Apple products. An integrated, simple experience and the convenience the customers failed to get from other disintegrated, ugly-in-design, and unnecessary complicated products. That experience ranged from production to sale, something Apple competitors had not provided.
Thinking out of the box may do well in Art where the audience is an individual who may or may not connect with the work. The market is not a single person but it comprised of different in taste and pace of accepting changes. Jobs was a brilliant marketer.