4. Bill Murray, Chestnut Salesman
You might be disappointed with your first post-collegiate gig, but at least you didn't have to sell chestnuts. Two years after dropping out of school, Murray was hocking hot nuts (yeah, it felt dirty writing that) in front of a grocery store. Unsurprisingly, chestnut sales didn't exactly pan out for Murray, who soon went to study at Second City with Del Close at the prompting of his brother, Brian.
Things started to fall together for Murray after studying comedy in Chicago. The next stop was Saturday Night Live before he was able to draw on experiences from his first day job at a golf course for his role in Caddyshack.