Abstract: ‘I try to explain to him the teddy is throwing a kink into our Kerouac On The Road cool, but Matt’s committed to his bear, so we drive on.’ Bruce Springsteen, Born To Run autobiography When Bruce Springsteen appeared on BBC Radio 4’s Desert Island Discs at the end of 2015 he did not mention author Jack Kerouac in the list of writers he would consider for his book choice. However, his reference to Kerouac and the teddy bear in his autobiography (above) perhaps reveals stronger, if stranger connections than he imagined, with Kerouac ending the key work On The Road looking over ‘the long, long skies over New Jersey’, Springsteen’s home state, where ‘tonight the stars’ll be out, and don’t you know that God is Pooh Bear?’ Unlike, then, the physical proximity of Allen Ginsberg to Bob Dylan, or the overt creative influence of Jack Kerouac on music characters such as Patti Smith and Tom Waits there is, at first glance, no obvious link between Jack Kerouac and Bruce Springsteen. This chapter, however, will explore and then uncover the links that do, in fact, exist between the two. These can broadly be defined in three ways. Firstly, there are sartorial connections in the way the two men dress and present themselves, with Springsteen adopting the jeans, T, and work-shirt look that very much defined The Beats. Secondly, there are obvious thematic links between the musical and literary work of these two icons of American popular culture: a mythologising interest in blue collar, small town America and the way it harbours past love affairs; male friendship; the open road and the freedom it suggests. Finally, there are defined stylistic links in the free-flowing lyricism that defines the words and worlds of both men. Although these three areas provide the main focus for this account other synergies may also be seen between the two: their European heritage; troubled relationship with patriotism and the American flag; family dynamics; Catholicism. More than anything, however, this chapter will explore the ways Jack Kerouac was able to make literature powerful in a new and alluring way, and similarly how Springsteen was able to engage globally, musically, in a way that could never have happened without Kerouac’s influence. Key words: Bruce Springsteen, Jack Kerouac, Beat Generation, Rock Music