In recent years, there has been a scholarly debate regarding the decrease in automobile-related mobility indicators (car ownership, driving license holding, VMT, etc.). Broadly speaking, two theories have been put forward to explain this trend: (1) economic factors whose impacts are well-understood in principle, but whose occurrence among young adults as a demographic sub-group had been overlooked, and (2) less well-understood shifts in cultural mores, values and sentiment towards the automobile. This second theory is devilishly difficult to study, due primarily to limitations in standard data resources such as the National Household Travel Survey and international peer datasets. In this study we first compiled a database of lyrics to popular music songs from 1956 to 2015 (defined by inclusion in the annual “top 40”), and subsequently identified references to automobiles within this corpus. We then evaluated whether there is support for theory #2 above within popular music, by looking at changes from the 1950s to the 2010s. We demonstrate that the frequency of references to automobility tended for many years to increase over time, however there has more recently been a decline after the late 2000s (decade). In terms of the sentiment of popular music lyrics that reference automobiles, our results are mixed as to whether the references are becoming increasingly positive or negative (machine analysis suggests increasing negativity, while human analysis did not find a significant association), however a consistent observation is that sentiment of automobile references have over time become more positive relative to sentiment of song lyrics overall. We also show that sentiment towards automobile references differs systematically by genre, e.g. automobile references within ‘Rock’ lyrics are in general more negative than similar references to cars in other music genres). The data generated on this project have been archived and made available open access for use by future researchers; details are in the full paper.