The charismatic Don Draper from Mad Men was a mastermind of advertising. It’s not just that he was a creative genius, though, he was also an outstanding salesperson. He had a presence that dominated every room he entered, so it’s no wonder he was regarded as one of the company’s most valuable assets.

Even though Don Draper’s ad agency was brimming with questionable workplace choices, he excelled at his job. Most of his pitches were an instant success. Unfortunately, some of his work didn’t sit well with the clients, regardless of how ingenious the campaigns were.

10 Life Cereal

Don was very drunk during his pitch for Life Cereal, but it was far from the worst pitch featured on the show. Roger and Don came to the meeting straight after an award show, drunk on both alcohol as well as power.

Even though the clients didn’t like the pitched idea, Don wasn’t discouraged. He just kept on spitting ideas at their faces until they liked the slogan that the genius ad man actually stole from another guy: “The cure for the common breakfast.”

9 Lucky Strike

Don Draper’s sharp mind and charisma first shines during the Lucky Strike meeting in the pilot episode of Mad Men. The clients were unhappy: doctors started advising people against smoking, so they could no longer advertise their product as safe.

Don saved the meeting, though. “We have six identical companies making six identical products,” he told his clients. “We can say anything we want.” Then, he encouraged his clients to explain how cigarettes are made and so, he came up with their next slogan – “It’s toasted.”

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8 Dow Chemical

When Don and Roger came to sweet-talk Dow Chemical, they weren’t pitching an ad – they were offering their services. The conversation Don had with them proved that he wasn’t just a creative genius. He was also an amazing salesman.

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“You’re happy because you’re successful – for now. But what is happiness? It’s a moment before you need more happiness,” he told the businessmen before standing up and thus ending the meeting. It was Don Draper at his finest: assertive, confident, and persuasive.

7 Playtex

The ’60s were a different time. As was evident in the pitched Playtex advertisement, society, as a whole, was far more sexist and demeaning to women.

The Jackie & Marilyn dichotomy was Paul’s idea and it made the men in the office objectify their female coworkers, but Don presented it with elegance and style. “Nothing fits both sides of a woman like Playtex” was the slogan and the clients instantly ate it up.

6 Jaguar

Don’s pitch for Jaguar was the only good thing about that account. And even though it was one of his finest monologues, it was Joan’s sad sacrifice that ultimately won the account. Don likened the stunning car to a gorgeous woman: “Oh, this car — this thing, gentlemen — what price would we pay, what behavior would we forgive if they weren’t pretty, if they weren’t temperamental? If they weren’t beyond our reach, a little out of our control, would we love them like we do?”

The comparison is, without a doubt, painfully problematic, and this point was hammered home beautifully with a montage of Don talking and Joan going to meet Herb.

5 Hershey’s

It’s hard to say what’s sadder about Don: the fact that he had a difficult childhood or the fact that he had kept it all a secret that gnawed at his heart. His Hershey’s pitch started with a made-up story about his childhood. He told the clients how his father used to buy him a Hershey’s chocolate and that it was like a symbol of love.

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Since little Don found great solace in their product as a kid, he felt compelled to tell everyone in the room the truth about his childhood and how much the chocolate meant to him. It was one of the show’s most emotional scenes, so fans naturally adored it. The clients – not so much.

4 Hilton Hotels

Don’s vision for Hilton Hotels was to make the company’s name synonymous with the comfort of a hotel. “Hilton – it’s the same in every language” was the motto. It was one of the wittiest and ingeniously simple campaigns on Mad Men.

The customer is always right, even though they have no idea how to sell hotels. Don’s vision for Hilton Hotels was outstanding, but the clients didn’t like it at all. What they wanted was the moon and Don didn’t respect their wishes.

3 Heinz Ketchup

Very similar to the Hilton Hotels idea was Don’s pitch for Heinz Ketchup. His million-dollar idea was the slogan, “Pass the Heinz.” The clients didn’t like it, though. They wanted to see the bottle, but as Don told them, it was the imagination of the consumer that was their biggest asset.

Even though it was among Don’s top pitches, Heinz didn’t go with it. It was simply too modern and forward for their taste.

2 Belle Jolie Lipstick

When the clients criticized the “Mark your man” pitch, Don stood up and essentially re-pitched the idea in a far more convincing way than Freddy before him.

Every woman wants choices, but in the end, none wants to be one of a hundred in a box. She’s unique. She makes the choices and she’s chosen him. She wants to tell the world he’s mine. He belongs to me, not you. She marks her man with her lips. He’s her possession. You’ve given the gift of total ownership.” Everybody in the room was left speechless by his performance, and so the agency signed a deal with Belle Jolie.

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1 The Kodak Carousel

The Kodak Carousel is Don’s greatest pitch by far. He understood that what sells things isn’t just the product itself, but also “a sentimental bond with a product.” He then proceeded to explain the meaning of nostalgia and made some grown men cry.

“This device isn’t a spaceship, it’s a time machine. It takes us to a place where we ache to go again,” he told the room as he showed them snippets of his family life. While fans could shed a tear in the privacy of their own homes, Harry Crane got so emotional that he had to leave the room.

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