In between, Gyllenhaal has moved easily between independent dramas ('Donnie Darko,' 'The Good Girl,' 'Lovely & Amazing') and big-budget Hollywood projects ('The Day After Tomorrow,' 'Zodiac,' 'Prince of Persia: The Sands of Time'). In 'Love and Other Drugs,' he got just as naked as Anne Hathaway, but somehow ended up with less attention, which probably says more about audiences in general than it does about his performance. Before the film slid into melodramatic territory, Gyllenhaal's facility with comedic material was nicely showcased, a side of him that has surfaced only rarely.
For his funny side, though, you can go straight back to his feature film debut as a pre-teen in a little box office smash called 'City Slickers.'
'City Slickers' starred Billy Crystal, Daniel Stern and Bruno Kirby as friends who are all facing a mid-life crisis. They decide to visit a more authentic version of a dude ranch and join a cattle drive to recapture their youth. Veteran cow wrangler Jack Palance teaches them life lessons and whips them into shape. Palance won an Academy Award for his performance.
Gyllenhaal played Crystal's son Danny, a kid who's not exactly proud of his father's profession -- he sells ad time for a radio station. It's a brief role, and hardly memorable on its own merits, but Gyllenhaal is a cute kid. He was born in December 1980 and the film was released in June 1991, which means he was no more than 10 years of age when making the film.
Somewhere around the time of the film's release, he was involved in its promotion. Check out the interview below with a British TV show, in which he gives credit to his parents, demonstrates his double-jointed arm and expresses his hope to do more movies "like that."
Gyllenhaal, even as a child dressed up in a cowboy hat, looks very serious as he discusses his craft, and displays an engaging smile. Could anyone imagine that, 14 years later, he would be nominated for an Academy Award for his performance in 'Brokeback Mountain'?