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This article analyzes Late Night with Jimmy Fallon’s musical performances and booking practices to claim it as a site of recording industry and intermediary labor. These traditions exist within the late-night talk format, a holdover from broadcast-era television programming that was indebted to radio’s industrial model. Late Night represents the format’s relationship to music alongside paradigm shifts in recording industry labor practices. It also demonstrates late-night talk and the recording industry’s efforts to utilize social media. To better understand the evolution of these intermedial industrial practices and their historical underpinnings, I evaluate the labor relations between musicians, bandleaders, and booking agents. I do this to show how Late Night broke emerging recording artists who used edgy aesthetics and networking savvy to negotiate questions of identity and representation. To do so, I engage in textual analysis of the show’s musical performances and Twitter presence. I employ this method alongside discourse analysis of press coverage to argue that Late Night serves as a productive space for recording artists and intermediaries’ negotiation between broadcast network television and social media’s labor paradigms. I first analyze Roots’ drummer Ahmir “Questlove” Thompson’s work in shaping the show’s musical identity as its bandleader and music director alongside music booker Jonathan Cohen. I then evaluate network-debut performances from Odd Future collective members’ Tyler, the Creator and Frank Ocean, the latter following a much-discussed Tumblr post about his affair with another man and his ambiguous queer status.