In this chapter, I deal with the complex relationship between jazz and cars in North America. I situate the relationship historically, discussing the discursive alignment between jazz and cars in the 1920s. I suggest that this alignment was founded upon the role of Fordist mass production in the parallel proliferation of both jazz and cars in the American mainstream: while cars rolled off of Ford and GM assembly lines and into newly-paved driveways across the country, jazz made its way into American homes through the emergent technologies of radio and the recording industry. From the 1920s, I jump ahead to the 1950s, a period that marked the coincidence of the so-called “Golden Age” of car culture with the waning years of what is often as the “golden age” of jazz: the “Big Band Era”. Next, I broaden my scope to consider the jazz-automobile relationship in a more global context, discussing the European and Australian campaigns for the Honda Jazz, a small hatchback that was launched in the EU, Australia, Africa, and Asia in 2001. In the third and final section of the chapter, I look to my first principal case study: Chrysler Canada’s spot for the 2003 Sebring featuring Diana Krall, entitled “The Look of Love,” examining how that advertisement inadvertently reiterates the troubling historical marginalization of women in jazz.