Jay Leno 's new show , titled '' The Jay Leno Show '' , debuted on September 14 , 2009 . It was announced at the Television Critics Association summer press tour that it would feature one or two celebrities , the occasional musical guest , and keep the popular " Headlines " segments , which would air near the end of the show . First guests included Jerry Seinfeld , Oprah Winfrey ( via satellite ) , and a short sit-down with Kanye West discussing his controversy at the 2009 MTV Video Music Awards , which had occurred the night before
2009 MTV Video Music Awards
2009 MTV Video Music Awards
Jay Leno