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A Comprehensive Review Of Bob Dylan’s Career, Starring His 2014 Chrysler Super Bowl Ad

Everybody has a Bob Dylan story, and over the years I must have heard all of them. The stories are incredible. They all seem to be handed down, based in a surreal and beautiful oral tradition that is rapidly fading from us as the hippies start to die out. And Bob Dylan, of course, hovers around all these stories like a ghost. These are stories as diverse as America itself, and I doubted all of them, but they all shared one common truth: Bob Dylan lives in a huge house on Point Dume.


For years I studied his career, and today I am satisfied that my journey is done. I came away conflicted, as all Dylanologists do, but I learned everything there is to learn about America in the process, and I do not regret it for one second. Here now is my review of Bob Dylan’s career, with highlights in descending order, like you do.

3. Victoria’s Secret (2004)

My journey got off to a rocky start with this 2004 Victoria’s Secret advertisement. A good pitchman is defined by his ability to sell me a product. It’s just that simple. Does this commercial make me want to spend my hard-earned money on what you’re selling?

Bob Dylan does not mention the product at all. Instead, he stands there in a cowboy hat, moping around like an old dog. This does not instill confidence in the product. And the overemphasis on music feels like a trick. Smoke and mirrors, designed to intoxicate me into falling for a product instead of making a rational purchasing decision.

It is difficult to believe that Bob Dylan could attain such a large house with a commercial this fundamentally poor. He does not once mention the women’s underwear he is selling. I know nothing of what sets this underwear apart from any other brand. Moreover, I don’t care.

The worst failing, however, is how innately uncomfortable the commercial is. I can’t watch this with my children. There is a virtually naked woman on-screen for over half of the running time and Mr. Dylan, dressed inexplicably like a riverboat gambler, suggests we’re looking at a brothel. Not only does he make me disinterested in buying the product, he makes me want to actively shun it. He’s laughing at somebody in this advertisement, and it feels a lot like me. He’s making fun of the buyer. That’s terrible for the brand. An inexcusable failure.

0 stars out of 4.

2. Chrysler 200 (2014)


A decade later, and Bob Dylan is a different person. This represents a massive amount of maturation. It’s like looking at a different pitchman altogether. Where Bob Dylan failed outright at selling women’s underwear, here he has confidence of the sort you can’t fake. I can tell he believes in this product. He’s even talking. There’s no sense that he feels above his audience anymore.

But while his technique has improved, his message hasn’t. It all comes across as muddled and needlessly confusing. The first line of his pitch is a throwaway. “Is there anything more American than America?” he asks us. What a waste. He has conviction but no message to back it up. This is not related to the Chrysler 200. It sounds like something Peter Griffin would say in Family Guy. The purchase of a car is a major life decision. Take your buyer seriously.

Things get worse from there. Soon we see Bob Dylan playing a guitar. This is completely irrelevant. Tell me about the car. Show me the car, Bob Dylan. It takes almost 58 seconds before we see the Chrysler 200 at all, and even then its appearances are sporadic. I watched this advertisement several times to confirm my suspicions, and the car has a mere 9 seconds of screen time. I have no idea what the interior looks like. I know nothing about the turning radius or MPG.


The advertisement is so dizzyingly ambitious that I’m tempted to give it 4 stars for entertainment value alone. But at the end of the day, I don’t know what I’m buying. Bob Dylan, you forgot what your job was here.

2.5 stars out of 4.

1. Cadillac Escalade (2007)

This is it. This is the masterpiece. As soon as I finished watching it, I immediately watched it again. This is where it all clicked and I understood all those stories about that house at Point Dume and more importantly its size, which is huge.

Why it’s a masterpiece, of course, should be obvious to everyone who watches it. If you don’t get it, then you’re just never gonna get Bob Dylan, and that’s a very sorrowful thing indeed. This is where the soul of man never dies.

Bob Dylan’s masterpiece opens guns a-blazing. It’s in widescreen, perfect for display in theaters before the feature presentation. Bob Dylan’s driving an Escalade through the rolling hills of America. He’s not talking about driving, not explaining the beauty of driving. He’s just driving. The Cadillac logo is right there on the bottom of the screen. This advertisement shows you the American dream without condescension. This is one man driving a car alone through his country. The Cadillac Escalade takes the American dream and puts it in your driveway, and Bob Dylan’s right there in the passenger seat, giving you the road map.

It’s so effortless, this depiction of America’s intimidating vastness, this depiction of speed and individuality, that you almost forget Bob Dylan is even selling you an Escalade. He’s selling you eternity for seventy thousand dollars. There is no pretense, no artifice – just a man and his luxury SUV, on his way to anywhere.

And where the Chrysler ad fails by forcing Bob Dylan to over-narrate a weak, abstract premise, this ad is so self-confident, so fully-realized, that all Bob Dylan has to do is take us on a ride with him. And when the ride has to end, as all rides must, he imparts a wisdom that only Cadillac can provide:

What’s life without the occasional detour?

4 out of 4 stars

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