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When I showed up to vote in Prior Lake on election day I couldn't help but notice the unusually long lines (I voted with the before work group just before 8 AM) made up of mostly young men in the 18-15 age catagory. I recall hearing that Jessie's campaign had made an extra effort to reach young blue collar types who typically didn't go to the polls and here was evidence of it on the day that counted.
In the TV coverage I saw prior to the election and the few times I observed his rallies first-hand, I did notice a lot of 20-30 year old supporters who were obviously, a) not scrub faced young Republicans or, b)Wellstone clones from the DFL. My impression was few of Jessie's kids had ever taken part in a political event or had any previous interest in elections--and I think the Ventura campaign targeted this group, knowing that, in a three way race, an extra ten or 15 percent of the population who generally ignore election day would make the difference.
Jessie's emphasis on rock music and connection with local musicians and bands probably was conceived by the former Wellstone connection he hired (recall Wellstone's first campaign was a "youth movement"). The advertising appealed to young people, including the "thinker" ad, with a semi-nude Jessie, in the last ten days of the campaign. Also consider the election-night rock concert (I forget where--Robbinsdale Ballroom?) that went on till 3 in the morning.
After the election, the newspapers were full of stories on how many new voters showed up to vote for Jessie. This was an easy story to prove because there were so many new voter registrations the same day (since the North Star State allows same day registration). I'd say Jessie worked pretty hard to "shock the world" as he put it on election night. Going after the young vote was pretty good strategy and I don't think the elction was handed to him while he was napping.
Respectfully,

You make a good point. Even if he didn't shoulder a lot of the work himself, he did have a good strategy, and executed it very well. I have long contended that without same-day, polling place voter registration, Jesse could not have won. The sort of voters you describe wouldn't have shown up in similar numbers even a day in advance to register and then again to vote.

Incidentally, on a note of trivia, did you realize that the famous "thinker" ad actually used a body double to play the role of Jesse's body? The only part that was Jesse himself was the closeup of his face at the end when he made his famous wink. He claimed it was because he didn't have the time to film the ad, due to campaigning. Rather implausible. I suspect the real reason was that Jesse wasn't in quite the shape he used to be. Through clever ads like that one he was able to keep his Herculean physical image in people's minds. Little things like that definitely matter in a close election (though that doesn't imply very nice things about the voting public).