By 2000, Maguire had obtained his GED to officially graduate from high school, noting that during his school days as a child, he’d reached a point where “I wasn’t doing school. DiCaprio got the part, and Maguire later got a guest role at least partially due to DiCaprio’s recommendation. The same scenario played itself out during casting for the 1993 movie This Boy’s Life (featuring Robert De Niro as the lead); DiCaprio got the main teen role (coincidentally, the character was named “Toby”) and Maguire got a part as one of Toby’s friends. in the 1998 film Fear and Loathing in Las Vegas he portrayed a hitchhiker who met Raoul Duke and Dr. Gonzo during their drive to Las Vegas. in Ride with the Devil (1999), Maguire performed as Jakob Roedel, opposite Jewel Kilcher.
Tobey Maguire Sued Over Illegal Poker Game Underground poker games happen all the time, we assume. What we don’t assume, however is that Tobey Maguire, Leo DiCaprio, Matt Damon, and Ben Affleck take part in them — especially the ones being run by a “Beverly Hills hedge fund manager who embezzled investor funds and orchestrated a Ponzi scheme in a desperate bid [...] [link]