In this thesis, I will examine modern reggaeton through a combination of musical analysis and interviews. Although there have been significant writings on reggaeton, its development, and its explosion in the late 90’s and early 2000’s, few have written extensively about the reggaeton of the last five years or so. Reggaeton has transformed significantly in recent years, especially with the progressive and experimental contributions of such artists as Bad Bunny. I will focus on the ways reggaeton has transgressed and transcended musical, cultural, and ideological boundaries by analyzing music award shows, events like the Super Bowl, as well as recent releases and music videos by reggaeton artists. I argue that recent changes in reggaeton have attracted a new generation of listeners, cultivating an increasingly diverse pan-Latinx identity in the process. Reggaeton has moved beyond standard genre conventions and is no longer defined by the dembow beat, but instead continues to develop into a broader style that is becoming more inclusive than ever before.