I'll answer the above question in a real weak way - it all depends, but in this case, not really. Frankly, I think the VW add that has gotten so much attention is more silly than sinister.
Here's the premise: a predominantly white setting - an office park, perhaps in the American mid-West, which features what appears to be a nearly all white, all make work force. One man is perhaps American, perhaps of east Asian descent. A handful of white women work there too. A white man from Minnesota imitates Jamaican patois as he goes around, smiling and spouting funny sayings to encourage everyone to be push away their Monday morning doldrums. In one clip he tells a clearly frustrated female colleague to "turn that frown the other way." The character is goofy and when I see it, I don't see anything that remotely resembles Jamaican or West Indian people, or even an attempt to mimic Jamaican people. If the presentation of a clearly non-Jamaican person tried to do that - in satire or even in an exploitative way - that would be, as NY Times columnist Charles Blow said, "black face with voices." But I don't think that's what is happening here.
This commercial spoofs Americans and Westerners, mostly white, but perhaps of any color, who adopt a cartoon-like version of West Indian and Caribbean style and aesthetics as a means of stepping outside their own seemingly humdrum social and professional worlds. Think of the American tourists who spend a week in Montego Bay and braid their hair and burn their skin as a means of vacating from their everyday lives of work and kids and commuting. I think the ad makes fun of those people more than anything or anyone.
A clearly satiric - and I think hilarious - spoof of white Americans "playing Jamaican" is Andy Samberg's character, "Ras Trent."
Samberg is much clearer about who is the butt of his parody: white privileged college students who play at being Rastafarian as a means of rebelling against class, religious and parental conformity. But Ras Trent and the character in the VW commercial are two sides of the same coin - privileged Americans with money who escape via what they imagine to be authentic, carefree, happy Jamaican culture. In truth, both the VW and the Ras Trent spook tell us more about the vapidness of those privileged Americans than about Jamaica or its people.
Before I saw the VW add, I heard about it on the Public Radio International radio program, "The World." The podcast is available here:
The podcast features an interview with Karen James, a journalist in Kingston, Jamaica. Her analysis is smart and basically, without directly saying so, I think she lets-on that the reason many Jamaicans are not offended by this add is that they are laughing at silly Americans making fools of themselves wasting money getting high and drunk and what have you during their Caribbean get away.
There are real exploitative issues at work in Jamaica's relationship with the wider world, namely that a place like Jamaica faces problems of debilitating poverty while at the same time serving as an international playground for massive levels of conspicuous consumption through its tourism industry.
Unfortunately, the VW commercial has not prompted conversation about that type of economic exploitation and imbalance.
And this is where I part ways with Karen James's analysis. She welcomed the VW commercial as a positive presentation of Jamaica and Jamaican people. (She even made an interesting argument about how the commercial uplifts Jamaican patois as authentic language, although it is ironic that a white American male playing Jamaican becomes the international vehicle through which Jamaican linguistics attains legitimacy.) As a journalist beset with the everyday problems Jamaicans face - poverty in the midst of plenty, and crime, violence, economic segregation - she no doubt saw this commercial as a chance to embrace a lighter side of life in her home, the side in which Jamaicans promote positivity and happiness to the jet-setters, wedding parties, spring breakers, and middle and working class vacationers who come to the island's white beaches to spend a week or so forgetting about their first-world problems. Perhaps, for a change, a spoof of how silly vacationing Americans look when they bring back their sing-song West Indian speak to their banal office parks can offer beleaguered Jamaicans a respite from their troubles. I can't fault her for feeling that way.
But I wish that instead of debating whether or not the VW add is racist, Americans could have a serious talk about how economic exploitation shapes life Jamaica, and about how international trade policies and histories of colonialism make possible that inequality, as well as Americans' enjoyment of it via tourism. In short, let's have some intelligent national talk about the themes raised in the 2001 documentary film, Life and Debt.
Because just like VW will laugh all the way to the bank through this parody of Americans playing West Indian, someone is getting rich off all of the decadence American tourists experience during the sun fun weeks in Jamaica.
And it certainly isn't the vast majority of Jamaicans.