Starting as an NBC page in the mid-80's, Jim Pitt eventually landed a dream job, for many: music booker for Saturday Night Live. From Nirvana's debut on network television to Sinead O'Connor's impactful and headline-making performance, Pitt booked it all starting in 1990, including mega-star appearances from Whitney Houston, Bruce Springsteen and Neil Young. Three years in, Pitt took his talents to David Letterman's replacement at Late Night, a young upstart named Conan O'Brien. There, not only would Pitt give future Rock Hall inductees like Radiohead, Green Day and Sheryl Crow their first-ever US TV performances, but O'Brien's unique wit often led to household names like David Bowie and U2 participating in hilariously scripted bits. On today's show, Pitt recalls all of this and more, walking us through decades of amazing television memories, as well as his move from Conan to Jimmy Kimmel Live! in 2017, and when exactly hosts began holding up vinyl again for the home audience, versus compact discs. Follow Jim on Instagram @jimpitt13, and watch Jimmy Kimmel Live! on your local ABC affiliate.