Mad Men: The 5 Times I Hated Don Draper The MOST! 😡

In the acclaimed series ‘Mad Men’, character Don Draper, portrayed by Jon Hamm, possesses numerous commendable traits. However, he also engages in actions that are deeply regrettable, and here are five instances where I found myself most disheartened by Don. The charismatic creative director at Sterling Cooper Draper Pryce, Don Draper, is a multifaceted figure reflecting the times, where womanizing, heavy drinking, and conduct that would lead to cancellation in today’s world were common among Madison Avenue advertising executives during that era.

Despite numerous mistakes, there are just as many instances where Don Draper, the character from Mad Men, shines at his finest. When he chooses to be, Don can display qualities of a loving husband and father, an inspiring mentor to Peggy Olsen (Elizabeth Moss), a reliable friend, and a genius in his role as an advertising professional. At times, Don takes a lone stand when it comes to doing what’s right, such as when he encouraged Joan Harris (Christina Hendricks) not to resort to prostitution to secure the Jaguar account for SDCP.

In the TV series “Mad Men,” it’s worth noting that while Don Draper (Don) initially displays some questionable behaviors, such as being selfish, callous, and an alcoholic, these traits intensify as the show progresses. His deceitfulness and infidelity wreak havoc on his marriage with Betty Draper (January Jones), leading to an increase in Don’s drinking habit during season 4.

Although Don exhibits numerous harmful actions throughout the first three seasons of “Mad Men,” his behavior deteriorates further as the series unfolds. Some of Don’s most disheartening moments are linked to his alcoholism and his treatment of his second wife, Megan Calvet (Jessica Pare).

5. Don Sleeps With His Secretary, Allison

Mad Men Season 4, Episode 2 – “Christmas Comes But Once A Year”

In the fourth season of Mad Men, character Don Draper stepped over a boundary when he engaged in a romantic relationship with his secretary, Allison (portrayed by Alexa Alemanni). Compared to Peggy and Jane Siegel (played by Peyton List), Allison stood out as a superior assistant. However, Don exploited the feelings Allison had developed for him during the Sterling Cooper Draper Pryce Christmas party, which resulted in him sleeping with her while intoxicated. Allison was left devastated when Don tried to downplay the incident and gave her money as a Christmas gift instead of addressing his actions sincerely.

As a movie reviewer, I can’t help but express my dismay at Don’s callous and reckless behavior towards Allison in “Mad Men.” What made this behavior more appalling was his frosty treatment towards Roger Sterling, who had the audacity to marry Don’s secretary, Jane. It became increasingly clear that Don’s perceived superiority over Roger was nothing more than a facade, as we later learn that not only did he have an affair with Allison, but at the end of season 4, Don himself marries Allison’s replacement, Megan. This revelation served as a stark reminder of Don’s habitual deceit and lack of personal growth throughout the series.

4. Don’s Alcoholism Is Completely Out Of Control

Mad Men Season 4, Episode 6 – “Waldorf Stories”

In the fourth season of Mad Men, episode 6 titled “Waldorf Stories,” Don Draper’s struggle with alcoholism reached new heights. Having won a CLIO Award, Don found himself intoxicated and disregarding his own principles by proposing slogans for Life Cereal in a meeting, without any prior preparation. To make matters worse, the dreadful tagline that Don had sold to Life Cereal was actually created by Danny Siegel (played by Danny Strong). Realizing this oversight when Peggy pointed it out, Don was forced to repurchase the slogan and offer a job to Jane’s cousin as a result.

In “Waldorf Stories,” the portrayal of Don’s alcoholism was arguably the most raw and unfiltered in the series “Mad Men.” Caught up in his alcohol-induced stupor, Don lost count of days and found himself involved with multiple women, including a waitress he introduced as Dick Whitman. Sadly, this weekend marked the time when he should have been with his children, but due to his alcoholism, he neglected his custody responsibilities. Throughout “Mad Men,” Don’s alcoholism remains unchecked, but in “Waldorf Stories,” we witness him at his absolute lowest point, struggling and sinking to rock bottom – a scene that was hard to watch unfold.

3. Don Hates Megan’s Birthday Present

Mad Men Season 5, Episode 1 – “A Little Kiss”

In a surprising turn of events, season 5 of Mad Men started with Megan unexpectedly throwing a party for her newlywed husband, Don. To make things even more uncomfortable, Megan sang a sultry French song, “Zou Bizou Bizou,” leaving Don and their colleagues from Sterling Cooper Draper Pryce rather mortified. Despite putting on a brave face during the celebration, Don secretly felt dismayed by the entire situation and was furious with Megan for causing such embarrassment. The mockery from Roger Sterling and Lane Pryce at work only added fuel to Don’s growing anger towards Megan, signaling the beginning of their relationship’s downfall.

During season 5 of Mad Men, Don was on an extended honeymoon with Megan, but there were already signs of trouble in their marriage from the start. This became more evident when Don lost respect for Megan after she performed a risqué act at a surprise party he didn’t approve of.

2. Don Abandons Megan At Howard Johnson’s

Mad Men Season 5, Episode 6 – “Faraway Places”

In the fifth season of “Mad Men,” episode 6 titled “Faraway Places,” Don Draper’s behavior towards Megan reached an unforgettable low. Instead of supporting Megan during a presentation crucial to Peggy’s team, Don insisted on taking Megan with him to scout Howard Johnson’s as a potential client. When Megan made a joke about liking orange sherbet which upset Don, he lost his temper and walked out on Megan at the restaurant.

In this situation, there’s no solid ground to justify Don’s actions in leaving Megan. He exploited his position as her superior to keep her away from work against her will, and there’s simply no valid reason for abandoning her. Of course, Don was concerned about Megan’s absence when he returned, but he was enraged by her decision to take a bus home. At that juncture, Megan should have ended the relationship, but their marriage ultimately never regained its footing. Despite occasional joyful episodes, they eventually went their separate ways, leading to their divorce.

1. Don Lies To Sally After She Catches Him Sleeping With Sylvia

Mad Men Season 6, Episode 11 – “Favors”

In the sixth season of the show ‘Mad Men’, Don Draper stopped pretending to be faithful to Megan and instead started having an affair with their neighbor, Sylvia Rosen (played by Linda Cardellini). This secret relationship went on even though Megan and Sylvia’s husband, Dr. Arnold Rosen (Brian Markinson), were both nearby. It was Sally Draper (portrayed by Kiernan Shipka) who eventually discovered Don and Sylvia’s tryst. Instead of admitting his actions, Don attempted to feign innocence and even tried to manipulate or confuse his daughter about the situation.

As a devoted fan, I once admired and idolized Don over my own mother, much like Sally did when she was younger. However, the revelations about Don’s deceitful nature and infidelity in Mad Men season 6, episode 11, “Favors,” completely shattered my illusions about him. This realization left me feeling betrayed and disappointed, and I never truly forgave him.

On the other hand, Arnold Rosen genuinely appreciated Don as a friend. Yet, despite this friendship, Don didn’t hesitate to sleep with Arnold’s wife. Despite his many flaws, Mad Men manages to make us sympathize with Don Draper and see the good in him. However, his lowest moments serve as a stark reminder of just how much he falls short of our expectations.

2025-05-22 15:51