Rose Kennedy Schlossberg
If our grandmother were Jacqueline Kennedy, we'd sure as hell be over the comparisons. Such must be the life of Rose Schlossberg, daughter of Caroline, and owner of a not so vaguely familiar square styled head that looks like it'd do just fine balancing a pillbox hat. To see the aspiring comedian in action, check out her web series - End Times Girls Club. Because if there's anything the Kennedys were known for, it was being funny. Right?