Hosted: eight times (1989-1992, 1996-97, 1999, 2003)
Most of us would be more than happy to sit back every year and let Billy Crystal steer the Oscar ship. His humour is not too kind, but never too mean. His sense of comic timing is stellar and, perhaps most important, he loves and understands movies. More than any other host, he brought the Oscars into contemporary times by injecting himself into the year’s classic footage (a whole generation of mash-up artists owes him a debt). Crystal never seemed daunted by the task, which is absolutely crucial to doing it well. Crystal revealed the secret to his own success in a 2003 interview, shortly before his last (to date anyway) appearance as host. That first time hosting, he appeared onstage with a toothbrush in his pocket, a symbolic reference to his childhood, when he had stayed up as late as he could to watch the seemingly endless ceremony, toothbrush clutched in a small hand to serve as a microphone for his imaginary acceptance speeches. “I wanted that big audience to feel like the living room,” he said. He made himself feel comfortable, so he could make us feel comfortable. It worked.