As for Brown, he was an ex-governor, another similarity with Dean. He hadn't been governor since 1982. And I really can't think of a candidate from the past twenty years, with the possible exception of Jesse Jackson, who was as much of an outsider as Brown was in 1992.
Read this speech and tell me that the speaker was an "insider." Key phrases include "bought-and-paid-for politicians" and "the Incumbent Party up in Washington."
Also, he won the Maine caucus a week after the New Hampshire primary and the Colorado primary a week after that, when everyone else was still in the race.
Hell, even Bush did. Does this make him an outsider?
Look, I like Jerry Brown, and I do think he had good points during the 1992 campaign.
But if he was an outsider, it was only because he couldn't win higher office besides governor. He lost the presidency twice and the US Senate in 1982 to a fairly mediocre Pete Wilson.
Winning does matter.