I remember the first time I heard this phrase, in a job interview about three years ago. I had the reputation for being an outspoken iconoclast around those parts, so one of the interviewers, a future corporate asskisser type, asked me if I "thought outside the box". I think I muttered something like "Excuse me?", but what I was thinking was "What box? What the fuck are you talking about?" I didn’t get the job, which is good, since I didn’t have to work under idiots who use phrases like "Thinking outside the box".

That commercial (for what I can’t remember – effective advertising, eh?) which featured the phrase prominently debuted not to long afterwards, which I think helped drive it from buzzword to cliché. I recall using it (sarcastically, of course) in class while I was lecturing on Oedipus Rex. Oedipus was able to outwit the Sphinx when no one else could because Oedipus "thought outside the box". Big laugh, and it drove the point home. I love moments like those.