Bobby, as a character, did not did not progress or develop emotionally with the same depth and focus his sister Sally did, but there was still a noticeable change to his character as he grew older. After season 1, he was included in more episode narratives, but it wasn’t until season 5 that the character came into his own.
Bobby Draper was played by the same actor from season 5 onward, which allowed the showrunners to fully flesh-out the character. Retrospectively, most of Bobby’s iconic scenes are from the last two seasons; however, there were plenty of memorable moments earlier in the series as well, when the other actors portraying the character had a chance to shine. With four actors in the role throughout the show’s run, it would appear that Bobby Draper was a particularly difficult role to fill long-term.
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Maxwell Huckabee
Maxwell Huckabee played Bobby Draper in Mad Men season 1, appearing in seven episodes as the show was establishing the outwardly-appearing perfect nuclear family. He was just four years old when he made his first appearance in season 1, episode 2, “Ladies Room.”
Aaron Hart
Huckabee was replaced with Aaron Hart who stepped in to finish season 1 and stayed for season 2. One of his more memorable appearances is in season 2, episode 4, “Three Sundays”, when Betty demands Don to discipline Bobby for knocking over a drink with his toy robot. In a touching moment he later apologies to Don and asks about his own late father, the first significant emotional interaction we see between Don and his son. Hart even earned a SAG Award when the cast won Outstanding Performance by an Ensemble in a Drama Series in 2009. It’s unclear why both Huckabee and Hart didn’t work out, but John Slattery told ShortList in 2012 they had “about five Bobby Drapers,” but couldn’t seem to find one who wouldn’t “look straight into the lens.”
Jared Gilmore
In seasons 3 and 4, the torch was passed to Jared Gilmore who appeared in 16 episodes. While also playing the Bobby who bickers the most with his sister, he’s perhaps best remembered for his comments about January Jones, who played Betty Draper. Gilmore left Mad Men when he was cast as Henry Mills on ABC’s Once Upon a Time, and when asked what advice he had for the actor who would replace him, he told TV Guide: “She’s not as approachable as the others. She’s really serious about what she does. Everyone else is so nice.” He was also part of the ensemble who won an Emmy in 2010.
Mason Vale Cotton
Mason Vale Cotton was the fourth and final actor to take on the role of Bobby for seasons 5 – 7. He is best remembered for a standout moment in season 6, episode 5, “The Flood,” when Bobby comforts a black theater attendant shortly after Martin Luther King’s assassination, telling him ”everybody likes to go to the movies when they’re sad.” This is a significant moment for Bobby and for Don, who feels deep pride at Bobby’s emotional maturity. Bobby’s evident growth is also what allows Don to finally feel genuine love for his children after years of “faking that feeling.”
Finding a consistent child actor can be tough, but the show pulled through and Mad Men didn’t actually lose any credibility through these recastings. Each Bobby brought something different, and these role changes conveniently coincided with noticeable character growth, particularly in the later seasons. Perhaps the different personalities quite accurately mirrored what the tumultuous stages of a young child’s life are actually like, especially in the Draper household.