In this fictionalized docu-series, musician Jack Antonoff tours with his band, Bleachers, while tackling problems such as his tour schedule, finding a new manager, and pleasing his girlfriend back in New York City. By merging documentary with comedy, fans get a glimpse into Jack Antonoff's life and come to understand why he is constantly both thankful and sorry. The series was created in partnership with Sony Music Entertainment, and features well-known celebrity talents including Jason Mantzoukas, Colin Quinn, Olivia Wilde, Sara Bareilles, and Lena Dunham.