Matt Long, Jessica Paré

Every day, Watch This offers staff recommendations inspired by the week’s new releases or premieres. This week: In anticipation of Mad Men’s final episodes, special guest appearances from the show’s stars from before they went to work at Sterling Cooper & Partners.

Jack & Bobby, “The First Lady,” (season one, episode five; originally aired 10/10/2004)

Megan Calvet’s indelible, coquettish performance of “Zou Bisou Bisou” in “A Little Kiss,” the premiere episode of Mad Men’s fifth season, was surprising for a host of reasons, not the least of which was that the last time many had seen the actress playing her, it was in a drastically different role. Jessica Paré didn’t look the part of the future Mrs. Draper back when she was a regular cast member in the one-and-done family drama Jack & Bobby. The 2004 WB show focused on the lives of Jack and Bobby McCallister (Matt Long and Logan Lerman), Kennedy-esque brothers, one of whom ascends to the presidency in the year 2041. Paré’s Courtney Benedict goes on to become first lady to the future POTUS, so her character is nothing if not wholesome and scandal-proof; Courtney’s certainly not the type of girl to engage in the kind of psychosexual gamesmanship that defined Megan and Don’s relationship in its early stages.

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But like Megan, Courtney is no stranger to the image maintenance and identity sculpting required of a woman who is largely defined by her relationship to a very powerful man. In Courtney’s case, that man is her father, Peter Benedict, played by none other than Paré’s future Mad Men co-star John Slattery. Peter ascends to his own presidency of Missouri’s Plains State College, where Jack and Bobby’s mother Grace (Christine Lahti) is a professor. Courtney is forced to mingle uncomfortably with powerful, influential people with whom she can find nothing in common, and she struggles to find her place among a culture she doesn’t entirely understand. That dynamic is most pronounced in “The First Lady,” the Jack & Bobby episode to first delve into Courtney’s background. After attending a stuffy party for the college’s wealthy alumni, Courtney tells Jack about the defining moment of her life, when she stumbled into the garage of her family’s old home to find her mother dead after committing suicide via carbon monoxide poisoning. In that moment, Courtney gets the sense that she may too be doomed, and feels powerless over a life so defined by her relationships with others. Perhaps it was great preparation for Megan after all.

Availability: “The First Lady” is available as part of the Jack & Bobby: The Complete Series DVD set. It is currently for rent on Netflix and can be viewed in segments on YouTube.