We could never imagine anyone else playing Josh in "Clueless" (ugh, as if!), but, surprisingly, Paul Rudd wasn't originally interested in the part. "I thought Justin Walker's character, Christian, was a really good part," Rudd explained to Entertainment Weekly. When Rudd didn't end up with that role, he still had eyes for another part that still wasn't Josh. "Then I asked to read for Donald Faison's part, because I thought he was kind of a funny hip-hop wannabe," Rudd said. However, he added, "I didn't realize that the character was African-American."
After multiple auditions for the film, Rudd ended up accepting a role in "Halloween: The Curse of Michael Myers" instead. Luckily, filming for that ended earlier than expected, and "Clueless" casting director Marcia Ross was still searching for the perfect person to play Josh — so she gave Rudd a call to come in and read with the actress cast as Cher, Alicia Silverstone. "The chemistry was instant, the connection was just there," the casting director later told Metro. "They were just great together. You couldn't deny he was the right person to play Josh." The rest, as they say, is pop culture history.
