Time Line: May 1966 -February 1967
Plot: After the painful layoffs and cost cuts SCDP had to go through some months back, results are finally beginning to show. The agency has managed to win Heinz, and successfully re-sign Mohawk Airlines as well as sign Jaguar Automobiles. Signing an automobile account is a key and defining moment for any advertising agency in Madison Avenue and after years of struggle and hard work they have finally made it. Don, now a happily re-married man is going through a new lease on life. Blindly in love he begins to neglect his duties as Creative Director. He has just turned forty and has started to become careless at work.
Betty who seems discontent with her life with Henry has gained weight. She goes through the shock of a possible tumour, which after some tests turns out to be negative. Yet she does not seem joyous after hearing this for some reason. Openly jealous of Megan’s youth and beauty she starts to meddle in between her, Don and Sally.
The new important clients which undoubtly bring in extra cash to the firm ultimately cost them their values and dignity. Mohawk Airlines run by ex-army men more from Roger’s generation would feel uncomfortable with a female copywriter so the senior managers are obliged to push Peggy aside to write for minor accounts and sign a new young male copywriter, Michael Ginsberg (Ben Feldman) who turns out to be an eccentric genius. Peggy ultimately frustrated with her limited prospects at SCDP and yet once again, been treated poorly by Don quits and joins CCG, a rival agency as Copy Chief for a much better salary and future.
Michael proves his value to the agency and soon takes over a lot of Peggy’s work even posing a threat to Don’s charisma for his creative genius and humour to produce unique artwork.
Pete and his relentless appetite continue to bring in important accounts for the company. It is he who brings in Mohawk Airlines back and ultimately signs Jaguar. He oversees the correct attending to important clients like Heinz and also represents the company at award ceremonies. Yet on a personal level we see him hit new lows. He has a major fallout with Lane who beats him up in a memorable episode. He also manipulates Joan to sleep with one of the Jaguar board members to win the account.
Lane Pryce who initially seems more settled in New York and at the agency comes to realise he will inevitably and always be different from the rest of the partners, besides his fallout with Pete, we see a man undergo huge financial stress and burden with devastating results. Roger, now more frivolous than ever, takes LSD and comes to realise a lot from his past and present and divorces Jane. Megan who has been promoted to copywriter does well but somehow feels empty at her achievements and quits advertising to pursue her dream of becoming an actress.
The agency also starts to open up to a more diverse workforce. They hire Dawn Chambers, their first black worker to be Don’s secretary besides the aforementioned Jewish copywriter, Michael Ginsberg .
Critique One could argue that Season 5 is aesthetically the coolest of all of the Mad Men Seasons. And after all, isn’t aesthetics an important part of Mad Men? The beatnik attitude is definitely making way for the Hippie movement in young America. This is seen in a more colourful and bold dress attire the main characters start to don. But moreover, Season 5 is one of the rollercoaster’s of the series beginning on a high and ending on a brutal low (spoilers
alert – but admit it, this season is from 2012, if you haven’t seen it yet, it’s your own responsibility.)
One of the key episodes in Season 5 (The Codfish Ball) we see how the protagonist have their hopes built up only to be miserably shot down at the end. Don, bursting with pride for receiving an award for his creativity is devastated when he hears the main industry players will reward him but will not do business with him due to “The Letter”. Megan, whose parents are visiting, is disillusioned when her father, an intellectual and leftist scholar disapproves of her empty profession in advertising and materialistic lifestyle. Sally is traumatised when she accidentally walks on Marie (Megan’s Mother) giving felatio to Roger whom up until then she was slightly infatuated with.
Don Draper (John Hamm) – Season 5 begins with Don who is about to turn 40. His life finally seems perfect. He is married to a young, attractive and optimistic woman. Being a newlywed, he and Megan can’t keep their hands to themselves and lead a vivacious sexual life. He lives in a stylish penthouse overlooking Central Park. He spends some quality time with his children on weekends. He is still a powerhouse at the firm but suddenly a bit less, he is so happy in his personal life that he begins to pay less attention to work. Season 5 is all about how appearances are deceiving: slowly we start to realise that his relationship with Megan is not that perfect either, her open spirit sometimes clashes with his old fashioned ways and the couple argue often.
As mentioned previously, for the first time since we know Don, he begins to pay less attention to work. This frustrates Peggy who being an ambitious workaholic suddenly struggles to lead the creative team with his constant absentism.
Season 5 also sees Don at his noblest, trying to convince Joan not to give up her dignity for an account and defending her in front of the other partners, he is also 
a loving and caring father to his children when they come to visit him. He is shocked and angry when he finds out Lane has stolen money from him because of his debts but instead of publicly humiliating him by having everyone know, encourages him to resign and keep his dignity. For the first time we also see Don being loyal to his spouse (Megan) throughout the storyline. He is also warm and welcoming to her parents despite some perceived antipathy from his new father in law.
Yet Don is set in his own ways and likes having everything and everyone under control. He is taken back when Megan quits advertising because she sees it as a shallow industry and pursues her dream of acting. This puts a huge strain on their marriage.
He is even more shaken when his protegee and favourite Peggy quits SCDP to join their rivals CCG. He is angry that she choses to work with Ted Chaough, the creative director at CCG who is known as his main rival in Madison Avenue. This pushes him to aggressively pursue for new business relentlessly.
He is devastated at Lane’s suicide since deep inside was quite fond of him and is the only person in the office who knew his secret with his financial troubles. His guilt at inviting him to resign makes him believe he also pushed him to take his own life and suffers for it. At one point he begins to get visions of his dead half brother who also hung himself after being pushed away by Don who points to his “rotten soul” as the source of his pain.
Peggy Olsen (Elizabeth Moss) – Whilst still excelling creatively Peggy still has to endure sexist attitudes at work where important clients do not want female copy
writers pitching ideas to them and has to train a new male copywriter (Michael Ginsberg).
She fails to pitch a brilliant idea to Raymond from Heinz for an advert, which was exactly what the client was looking for because the client trusts Don and openly dismisses her for being a “young girl”.
Don’s constant absentism at work gnaws at her; she struggles to lead the team with him on a never-ending honeymoon and ends up working late almost every night. She interviews and trains Michael who turns out to be a creative yet excentric genius who takes up most of the projects for important clients ushing her to the sidelines. She is also responsible for training Megan, yet when she is constantly leaving early sometimes against her will, by Don she has to cover up for her.
This takes a toll on her personal life. Despite being in a happy relationship with Abe, the idealistic and political journalist, her workload makes her stay late most evenings. When he proposes her to move in together she happily accepts yet tries to hide her
disapppointment since she was expecting a marriage proposal.
After months of approval and recognition, Don’s rudeness towards Peggy resurfaces with the toll of having to pitch to Jaguar and after humiliating her yet again, she realises she has had enough and quits SCDP to join a rival advertising agency, CCG as their new Copy Chief for a better career and salary. Much to Don’s disgust, one of the founding partners, Ted Chaough, the agency’s Creative Director is considered his nemesis within Madison Avenue. By the end of Season 5 Peggy finally seems content and motivated at her new job
Pete Campbell (Vincent Kartheiser) – Pete now miserably living in the suburbs continues to excel at work being the main source of business for the firm. Yet still feeling unappreciated he now faces competition not just from rival agencies but rather from within SCDP itself, namely a jealous and petty Roger. He convinces Mohwak Airlines to come back to the agency and signs Jaguar Automobiles after an intial faux pas with them.
Yet on a personal level we see him being a leech at almost every level. When he finds out that Ken is a successful writer besides his work, he tells on him to Roger Sterling. He insults Lane crudely and receives a much deserved beating up at the office by the English financial manager. Discontent with his marital life and resentful for giving up Manhattan for the suburbs he continues to be a terrible husband. He sleeps with a prostitute whilst taking a client out for dinner (and later whoring). He clumsily flirts with a high school student whilst attending driving lessons. He has another extramarital affair with Beth Dawes, the wife of a fellow comuter who himself cheats on her with younger women in Manhattan. He actually develops a deep connection with Beth and is devastated to know that she regularly undergoes electroshock therapies to have memories erased from her brain whenever she becomes depressed at her own husband’s own infedilities.
Yet we see him at a new low whilst pitching to Jaguar to win their business. The new Head of the Dealers associations, a disgusting pervert makes it crudely clear that if Joan would sleep with him he would vote in their favour. He then slimily manipulates Joan and the partners to make it happen. Pete lets others know of his terribly low self esteem which could point to his questionable behaviour. At one point with Don and Ken who have come over for a friendly dinner to his home, the guests look at his daughter in admiration, he lets go a “I take no credit for her whatsover”. This phrase could point to a man with huge inferiority complex and why he feels his actions are somewhat justified.
Megan Calvé/Draper (Jessica Paré) – Megan now happily married to Don has been promoted to a junior copywriter. She enjoys working with Peggy, Stan and later Michael but sometimes feels she doesn’t fit in due to the predominant smugness in the group. She works hard at creating commercial taglines for clients, does well but is sometimes frustrated at Don whisking her off at his own will from the office. She is aware that this makes her look unprofessional and obviously shows how she got her new job and does not like it.
Her youthfullness and optimism contrast with the cynism of most of her peers when she prepares a surprise birthday party for Don. She expects a great party with fun, sex and groovy music but was not counting on some unwelcome reactions by some of the people she works with. Peggy who has a bit too much to drink has a go at Don for having to do extra work during the weekend since he is not taking care of his duties. She prepares a dance and song for Don as a present but being Canadian wasn’t counting on the prudeness of most of the American guests. What’s worse, some days later at work she accidentally walks into Harry making lewd and sexist comments about her in the office kitchen. What hurts her most is Don’s insensitive behaviour with her once all the guest have left. He tells her off for embarrasing him with a clear indication that for people of that social circle and age group a simple dance like the one she performs can shock them.
At work she does well, she proves to have a good insight, imagination and creativity and 
one of her ideas convinces Heinz to stay with the agency when they were tired of Peggy’s ideas and were scouting the competion. It is quite revealing that with this client she manages to do something that neither Peggy nor even Don could manage.
We also get an insight into her origins when her family comes to vist. Her family, highly disfunctional prove to be a constant challenge to her emotional balance. Her father a leftist scholar finds it hard to accept her materialistic lifestyle and empty profession in advertising. He is not going through a good time and fails to get his works published. His wife Marie cruelly emasculates him in public. Marie has an antagonistic relationship with Megan. She loves her daughther yet does not know how to express this properly and more often than not comes out as cruelly discouraging and negative.
Much to Don’s surprise Megan one day gathers the courage to give up advertising and pursue a future in acting. Her teammates intially do not understand her decision but finally accept that it is her choice and wish her luck for being brave enough to take this bold step. Megan however deals very poorly with the inevitable frustrations a performer always has to face when they begin and one day breaks down infront of Don. She aks him to use his position as partner to get her a job for an advert for one of the agency’s clients. Don who adheres to a strict code of ethics at his work initially rejects her plea but finally gives in which begins to chave his relationship with her.
Betty Francis/Draper (January Jones) – Betty is finding it hard to cope with her new married life with Henry. She has become a bored housewife who no longer wants to be paraded as a trophy wife clinging to some man’s arm at any social gathering, beit a successful advertising executive from Madison Avenue or an ambitious politician from the Republican Party. She spends most days with little to do at home and has visibly gained weight. From earlier ep
isodes we learn that Betty used to be a chubby girl and pressures Sally not to be one. Henry and her argue often now. When she goes to the doctor for a diet pills prescription she is shocked to learn that she might have cancer and chooses to call Don to tell him about it. He comforts her on the phone with the simplicity and warmth she often lacks from Henry.
Yet, openly jealous of Megan’s youth and beauty she hates the fact the children also bond with her and begins to meddle between her, Don and Sally. She ackwardly dyes her hair black in a failed attempt to be more accepted by her children.
Roger Sterling (John Slattery) – Roger has become even more frivilous at work. Now that Lucky Strike is definetely out of the picture he starts to scavenge from Pete’s accounts to see what he can find. His competition with Pete becomes really ugly. At one point he noses over his agenda and appears unannounced at a meetin
g with Mohawk Airlines. Pete is furious and pranks him to attend a fake meeting with an important client at 6 am. Yet knowing Pete he goes one step too far and publicly humiliates Roger infront of the whole staff when signing of Mohawk is announced making it look that Roger is his junior.
When Pete, who knows he is more important as far revenues go, asks to have Roger’s bigger and more stylish office, Roger reacts challenging him to a fistfight knowing too well that like him, Pete is a rich kid from a very priveldged background but unlike him, has never been tested in armed combat. This points out to a desperate Roger clinging to his status as an important partner with whatever means necessary no matter how unprofessional he chooses to be.
On a personal level Roger becomes one of the higher-class vivants who tries LSD in the 60’s and finds out a lot from his past and frustrating present. Whilst still high he has a deep and meaningful chat with Jane and divorces her. Once again, a rich middle-aged divorcee he embarks on a new spree of one night stands and shallow hookups plus a colourful and insane affair with Marie, Megan’s arrogant and insensitive mother.
Joan Holloway/Harris (Christina Hendricks) – Joan’s character evolves to new depths in Season 5. She has decided to keep her baby, a boy named Kevin whom she had out of wedlock with a one-night stand with Roger. With her husband away in Vietnam her mother has moved in to help her, something she finds difficult to deal with. When she goes back to work after her maternity leave she becomes one of the few people besides Don who understands Lane who becomes i
infatuated with her.
In the past Joan has always been objectified by most men in her life because of her physique. Greg, Her own husband, a failed surgeon with little character and no morale raped her some years back. Now we see Joan step by step take more control of her life. When Greg comes back after a year in Vietnam and then announces her to her that he has signed up for another year, she furiously breaks off the relationship with him reminding him of the ugly act he did.
When Pete manipulates her to sleep with one of the directors at Jaguar so that they could win the account she is disgusted but when falsely believes that the rest of the partners agree with the idea she decides she will not be a simple pawn in this ugly game but rather negotiates to her favour, first asking for a big fee and then later agreeing to a partnership securing her future and her son’s. Her connection and fondness for Don evolves further when he consoles her after she receives a letter of divorce from Greg and when he tells her that she should not go ahead with the Jaguar deal; that no one should have to do business with people like that. She respects him even more when she finds out that he did not partake in the agreement the other partners did come to.
Lane Pryce (Jared Harris) – Lane becomes the sad personification of tragedy within Season 5. (Big spoiler alert). What initially seemed to be an English expat finally settling in New York after years of complaints from his wife and meddling from his intrusive and abusive father, he seems happy and content. He has 
always made a huge effort to fit in America, but was never quite accepted by his peers because of his social ackwardness at times and their own narrowmindedess. When he makes a business connection with an executive at Jaguar he tries to manage the account but fails leaving the more apt Roger, Don and Pete to meet with him. When it all goes wrong, Pete insults him crudely and to his shock Lane challenges to him to a fistfight in the office and beats him up.
Despite we see his wife finally making an effort to settle in New York he fantasises with other women, including Joan but never does anything. Yet the depths of his personal failure become highlighted with his huge financial troubles.
Some months back when all of the partners had to supply with thousands of dollars each to save the company from bankrupcy, Lane moved money from his UK accounts to pay his share. The English Government claims back a penalisation for doing so and fines him for it. It is then revealed that whilst forming SCDP Lane settles for a much lower salary than the other partners and does not have enough money and time to pay this fine. Fearing being jailed for not paying on time in desperation he forges Don’s signature and hands himself a cheque to pay this amount promising himself to pay back that amount once the dust settles down.
Bert notices this and berates Don for what he thinks is Don handing out an unauthorised bonus to Lane. When Don angrily asks Lane about this, he ends up confessing. Don who has lost all trust in him aks him to resign, he offers him the chance to think up of a dignified excuse over the weekend and offer his resignation. Lane unable to face the humiliation of losing his job and petrified of having to go back to go back to England as a failure hangs himself in his office.
Sally Draper (Kieran Shipka) – Sally now more mature shows her aspirations to be seen as 
a young adult rather than a little girl. At home she asks to have dinner and have more grown up food with Betty and Henry rather than with ther little brothers. She constantly challenges her overbearing and old-fashioned step grandmother to have more freedom. When she has a domestic accident Sally takes good care of her earning the praise of Don. In fact Sally becomes somewhat of a bridge between the kids (her younger brothers) and the grown ups in her life.
She bonds with Megan and enjoys going out with her and her liberal friend, also an actress. Her closeness with Megan irks Betty who starts to meddle between both of them and Don. She tells Sally of Don’s previous marriage with Anna conveniently leaving out the details of how both of them supported each other. Sally who feels betrayed by Megan briefly becomes hostile with other until Don fills in the gaps of the story. Her relationship with her father continues being of admiration and emotional dependancy. She beams with pride when Don praises her for taking care of her step-grandmother.
She asks to go his awards ceremony and is joyous at his success. Yet this awards ceremony turns out to be an eye opener of the lack of morale also present in the grown up world. Roger who has been amusing her all evening briefly disappears during dinner and when she gets up looking for the washroom she accidentally sees him with Megan’s mother giving him fellatio. The crudeness of the scene shocks her since Marie is a married woman with her husband sat down at their table only a few feet away. When her friend Glenn asks her what she thinks of New York she calls the city “dirty” in a clear reference to this incident.
Michael Ginsberg (Ben Feldman) – Michael is one of the fresh new faces at SCDP. He represents change. A Jewish copywriter for the first time ever in the agency, he clearly stands out not only for this reason but also his wit, creative genius and eccentricity. He is hired at the signing of Mohawk Airlines who would reject Peggy as copywriter being a woman. During this time it was also fashionable in Madison Avenue to hire Jewish copywriters and therefore Michael is brought in. Despite seeming to be insane to Peggy when she interviews him he manages to appear witty, confident and charming
in his second interview with Don and is hired much to Peggy’s surprise.
Michael soon becomes one of the major creative forces at SCDP. He creates ads of immense quality and soon starts taking over Peggy as the main copywriter for most clients. He even poses a threat to Don at one point when both of them compete for artwork for an ice cream advert. Don aware that Michael’s idea is definetely better sabotages Michael’s work and presents only his to the client. Michael’s excentricity is further explained in a conversation he has with Peggy with both of them working late one evening. He reveals to her that he is an orphan who grew up in a concentration camp in Sweden and was adopted by his foster dad when he was five and came to New York. He also believes to be an alien from another planet, which throws Peggy back, who does not know how to react to this akward conversation.
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