The 80s and 90s gave us a lot of modern classics, like 'City Slickers,' that aren't just great movies, they are also treasure troves for finding actors before they got their big break. (Broke)back before Jake Gyllenhaal was cowboying around with Heath Ledger, or having visions of men in bunny suits, he played Billy Crystal's son in the 90's classic, 'City Slickers.'
See Jake in all of his pre-teen glory, looking oh so very 90s with the hightop haircut and chip on his shoulder. This was actually his first credited role, after which he worked consistently ever since. Makes sense since the movie was such a hit, and for a child actor, Jake pulls a solid performance. Unfortunately he didn't make it to the sequel, 'The Legend of Curly's Gold.'