A complete musical guest list of the Jay Leno Show, with photos! It's considered one of the greatest blunders in the history of network television, one of its largest bombs. When Jay Leno reached his scheduled retirement from the Tonight Show in 2009, NBC Universal chief Jeff Zucker moved to keep Leno from defecting to another network by giving Leno a new show, closer to primetime at 10pm. Zucker was desperate to replace NBC's expensive primetime shows with less pricey talk shows. The move was a disaster as both Leno, and his replacement on the Tonight Show, Conan O'Brien, tanked. After only four months, O'Brien was bought out of his contract, and the Jay Leno Show cancelled.