My favorite for obvious reasons is “Kennedy” by feeble little horse. See also: “Valerie” by Amy Winehouse, “Jolene” by Dolly Parton, and “Charlene” by Anthony Hamilton.
dog days - florence + the machine
edge of seventeen - stevie nicks
i wanna dance with somebody (who loves me) - whitney houston
you belong with me - taylor swift (i loved her in middle school so i probably have sung this into a hairbrush at a sleepover)
babooshka - kate bush
irreplaceable - beyonce
dreams - fleetwood mac
potential breakup song - aly & aj (ideally the new version where they curse) bubblegum bitch - marina and the diamonds naked in manhattan - chappell roan
you oughta know - alanis morisette
running up that hill (a deal with god) - kate bush
heart of glass - blondie
tears dry on their own - amy winehouse
criminal - fiona apple