Where does Bucket Head Bobby stand?

Credit: AMC / Courtesy Everett Collection

Over seven seasons of Mad Men, we watched Don Draper agonize, week after week, over how to sell American people in the 1960s nylons or cigarettes or lipstick. He was struggling to keep up in a strange new era — an America changing so much, in fact, that even the face of Draper’s own son never seemed to stay the same for very long.

In eight years of the series, there were no fewer than eight boys who played Bobby Draper, Don and Betty’s second child and oldest son. And now, fan favorite Kiernan Shipka, who played Bobby’s much more narratively significant big sister Sally, has taken to social media to celebrate the many faces of the oft-neglected character.

Weeks ago, Kiernan composed a list on the List App (which launched last month and is, as its name suggests, an app that enables you to create and share lists) of all the young actors who played her onscreen little brother, complete with photos and memories of each of them.

She fondly remembered the eight Bobbys chronologically. In addition to the four Bobbys we grew to know and (mostly) love, whom she titles Bobby #1–4, there is also Pilot Bobby (though she wasn’t Pilot Sally!) and Slurpee Bobby, who appeared, after being bribed with Slurpees, in the photographs for Don’s tear-jerking Carousel pitch in season 1’s “The Wheel.”

Kiernan also names Bucket Head Bobby and Pillow Face Bobby as “Supplemental Bobby Drapers” (whose faces we never really saw), both of whom she didn’t know well but remembers as being “chill” and “very nice,” respectively.

Maxwell Huckabee, a.k.a. Bobby #1, “holds a special place in my heart,” Kiernan writes. Aaron Hart, sweet Bobby #2, “had some pretty cool boots.” The controversial Bobby #3, Jared Gilmore, apparently had a taste for “eating packets of straight sugar.” And Mason Vale Cotton, our last (and greatest?) Bobby, “can rock a tux” — surely something he learned from his TV dad.

Check out Kiernan’s full list here.

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Thanks to costume designer Janie Bryant , Hamm's '60s ad man single-handedly revived an interest in the classic two-button suit.
Mad Men

Jon Hamm stars as Don Draper in the Emmy-winning ’60s-set drama

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