In "Rookie of the Year," Thomas Ian Nicholas plays Henry Rowengartner, although that almost didn’t happen. Director Daniel Stern ("Home Alone," "City Slickers") told Yahoo Entertainment that he initially offered the part to a young Jake Gyllenhaal.
“I met Jake when he did a little part in ‘City Slickers’” Stern recalled.
In his first-ever movie role, Gyllenhaal starred as Billy Crystal’s son in the 1991 film which co-starred Stern as Crystal’s best friend. On set, Stern noticed Gyllenhaal’s burgeoning talent, saying he had impressive depth for a kid.
“He was just such a good actor,” said Stern.
Stern added: “I think we offered [the role] to him but… [His parents] really had - and he did - a more serious-minded career … and you look at that career, good choice. He’s a more serious actor that way. It worked out.”
Stern noted that another buzzy actor of the early ‘90s, Jason James Richter ("Free Willy"), was also considered for the Rookie role. And at a certain point, Stern even thought about casting his own son, Henry (now a California State Senator).