YMMV: Jack & Bobby
- Harsher in Hindsight: Jack's track injury sidelines him for the season, and at first one is inclined to believe that usual teenage Wangst will be the only result...until the documentary from the future reveals that this injury gave Jack recurring pains in his knee; during the War of the Americas, he was unable to outrun enemy fire due to this recurring problem, resulting in his death.
- Hilarious in Hindsight: Roger Sterling was Megan Draper's father.
- Retroactive Recognition: Oddly enough, of a character name. Robert McCallister, moderate Republican...sound familiar? Rob Lowe's character on Brothers and Sisters was given the same name and political ideology due to the show being made by the same creators, including producer Greg Berlanti, who never got to fully explore Bobby's political career due to Jack & Bobby being canceled. That being said, the Brothers and Sisters version of Bobby drops out of the presidential race. And also, he's running in the present day (i.e. the early 21st century) rather than the 2040's.
- Bradley Cooper is the recurring character grad school student and Grace's lover interest Tom Wexler Graham.
- Tom Cavanagh appeared as the boys' uncle Jimmy, long before he was making the Flash's life miserable.
- The Scrappy: Missy. She does nothing but complicate Jack's life, first with her wanting to date him, the pregnancy scare, and her inability to see anyone else's position, cares only about herself, and worst of all, detracts the plot away from Jack and Bobby's development into their adult selves.