Despite Mad Men‘s reputation as one of the all-time great TV dramas, people forget just how funny it could be. In many ways, the show was a black comedy, offering up many bizarre situations, darkly comedic moments, and hilarious one-liners.
The show’s very soul is perhaps most strongly wrapped up in the character of Roger Sterling. Sterling mainly serves as the show’s comedic relief, but like everyone else, there’s an undercurrent of sadness and loneliness lurking just beneath his strong and confident surface. He’s certainly the funniest character, and also one of the most profound.
10 Funniest: “I Didn’t Think You Had It In You. And I Mean That.”
Roger is the master of the backhanded compliment, as evident by the absolutely hilarious line above. In the first season of the show, Pete and Harry come up with a rather clever plan for laxatives.
Cooper seems legitimately proud of the duo, but Roger can’t help himself from throwing out a hilarious backhanded compliment. Pete and Harry either don’t notice or ignore the quip, as they simply thank Roger and move on.
9 Profound: “Average.”
Roger can be quite profound without even realizing it. In season 3, episode 7 – titled Seven Twenty Three – Roger crams himself into the elevator and tells Don, “I watched the sunrise today. Couldn’t sleep.” When Don asks how it was, Roger simply answers, “Average.”
It’s funny, but it also speaks to a more upsetting truth about beauty and disappointment. Sometimes beautiful things disappoint, and sometimes people can’t see the beauty in a beautiful thing. Was the sunrise actually disappointing, or is Roger simply expecting too much?
8 Funniest: “Damn It Burt, You Stole My Goodbye!”
Few things bring Roger Sterling as much joy as firing Burt Peterson. Burt is originally fired in the premiere of season three but returns in the sixth season after the merger of SCDP and CG&C. Roger is quick to fire him again, and the entire sequence is comedy gold.
It’s filled with fantastic one-liners, including “Probably doesn’t make a difference at this point, but no one fought for you” and “No one will ever say you weren’t funny, Burt!” The best is when Burt says, “You’re a real prick, you know that?”, causing Roger to return with the greatest comeback in Mad Men history.
7 Profound: “Maybe Every Generation Thinks The Next One Is The End Of It All.”
The generational divide will remain a contested talking point for as long as humans exist. People have been complaining about the next generation for eons (as Roger puts it, “Bet there are people in the Bible walking around, complaining about kids today”).
The ’60s were no different, just as it’s no different in 2020. Roger shows an incredible amount of wisdom through this realization, and it strikes viewers as one of his most sincere and reflective moments.
6 Funniest: “You Ever Get Three Sheets To The Wind And Try That Thing On?”
One of the most bizarre decorations in Lane Pryce’s office is the random suit of armor. The armor is never really explained – perhaps it’s just a cool bit of decoration to make the office more interesting.
Roger isn’t concerned about where it came from or what it means, but if Lane has ever gotten drunk and tried it on. The line itself is funny enough, but what’s really hilarious is picturing the stoic and quintessentially British Lane Pryce getting toasted and walking around in a full suit of armor.
5 Profound: “A Lot Of Times In Life, You Get To Do Something And You Don’t Realize Until It’s Over How Much You Enjoyed It.”
As funny as the Burt Peterson firing moment is, it also contains a wonderful nugget of wisdom from Roger. Roger, relishing in the idea of firing Burt for the second time, utters the line. Of course, he uses the line as a bit of comedy – simply rubbing salt in Burt’s already festering wound of getting fired for a second time.
But it’s also a great piece of wisdom, not to mention a road map for enjoying life just a little bit more. Relish in the good and fun times, because they may be gone before you know it.
4 Funniest: “I Told Him To Be Himself. That Was Pretty Mean, I Guess.”
This line once again showcases just how little Roger sees in other people and that he isn’t afraid of launching a good insult – even against someone who’s related to him. Roger’s wife Jane convinces Roger to hire her cousin, Danny Siegel.
Danny is over-confident in his work and in the interview, and neither Don nor Peggy are particularly impressed. When Don goes to laugh about Danny with Roger, Roger launches one of his most vicious insults.
3 Profound: “Half The Time This Business Comes Down To ‘I Don’t Like That Guy.'”
Being likable and approachable is one of the most important things in business. The size of a resume only means so much when the person is hostile and disagreeable.
Roger knows as much – probably because Roger is one of the most likable men in the office – and also the one who is forced to put on his clown face and entertain the clients. While a naïve and inexperienced Don is learning what he can from Roger, Roger drops this nugget of wisdom – and Don certainly takes it to heart.
2 Funniest: “It’s All Fun And Games Until They Shoot You In The Face.”
Detroit jokes are easy to make. Apparently, it’s been that way for a while, as Roger was making Detroit jokes back in 1968. And easiness aside, the joke works for a variety of reasons – mainly Roger’s enthusiasm in telling it and the sheer brutality of the punchline.
Roger can make even the darkest joke funny thanks to his wild charisma, and he shows that off here thanks to his delivery and hilarious facial expressions – complete with the winning grin to Don and Joan that caps the joke.
1 Profound: “You Either Get Used To It Or Stop Thinking About It.”
There comes a time in life when you begin to think about death. For Roger, death seems a particularly troubling subject. He’s aging, he doesn’t take care of his body, and he’s already suffered two heart attacks. When Frank Gleason dies of cancer, Stan asks Roger how old he was.
Roger doesn’t seem particularly bothered by Gleason’s death, as he’s already a master on the subject. He simply tells Stan, “Older than you, younger than me. You either get used to it or stop thinking about it.” It’s unclear which choice Roger decided to make…
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