I'm going to go out on a limb here and bet that the guy pictured below never rises to become the CEO of a company.
I don't know anything about him other than his appearance, and my impression given the tattoos and piercings is that he rejects mainstream culture. This leads me to believe that he's not likely to be a cooperator. (I said I was going out on a limb.) His tattoos and piercings make him an uncertain candidate for employment. When the stakes are low, say, seeking an individual to fill a janitor position, there's not much of a risk in hiring someone like this. But when the stakes are high, say, finding a qualified and competent mid-level manager, the risks are greater and he's likely to be disqualified for the position outright. Again, I know nothing about this guy's qualifications, I'm simply stereotyping based on looks. Replace the tattoos with a doo-rag or missing teeth and he's likely to suffer the same discrimination, albeit maybe due to different inferences.
When you hear the term "used car salesman" you are likely to think of a cheat or a dishonest individual. There are certainly plenty of honest and ethical salesmen out there, but the initial impression most people have of used car salesmen is not one of integrity.
Whenever we enter into social relationships, either market or otherwise, we invariably deal with information asymmetries. Our expectations of others' behavior--mostly strangers, but not always--is usually based on group stereotypes. These stereotypes come from past experiences or from other forms of social learning such as our social peers and/or the media.
Although I wasn't as big a fan of the movie Crash as he was, Bryan Caplan has a good post on just this topic. Of importance is Bryan's following argument:
It is particularly interesting that Crash illustrates one of the deep truths of models of statistical discrimination: The real social conflict is not between groups, but within groups. People who are below-average for their group make life worse for people who are above-average for their group. Women who get job training and then quit to have children hurt the careers of single-minded career women, because they reduce the profitability of the average woman. This lesson is beautifully expressed in the scene where the successful black t.v. producer (Terrence Howard) chews out the black teen-ager (Chris "Ludacris" Bridges) who unsuccessfully tried to car-jack him:
You embarrass me. You embarrass yourself.
The upshot: If you really want to improve your group's image, telling other groups to stop stereotyping won't work. The stereotype is based on the underlying distribution of fact. It is far more realistic to turn your complaining inward, and pressure the bad apples in your group to stop pulling down the average.
Most people are far more understanding and accepting of stereotyping the tattooed individual than they are about stereotyping based on, say, race or gender. My guess is that this is so because someone with tattoos or a doo rag has self selected to be part of a group with a certain stereotype while someone of a specific race or gender hasn't. I can't change the color of my skin and I can't control the behavior of others with the same skin color as mine, therefore I am a victim of circumstances beyond my control. I can choose not to be tattooed, but I can't choose not to be black. But I don't think that this in any way diminishes Bryan's argument.
But since much of the information we acquire about the behavior of others comes from the media and from peers, a valid argument can be made that at least some stereotypes are unfair. (Again, this doesn’t diminish Bryan’s argument, only the party to blame for the negative image associated with certain groups.) For example, name a movie that portrays a young black male in a positive light. Not one where he is an affable buffoon such as Urkle, but one who is respected both within and outside his social group. The media and peer relationships are instrumental in defining how individuals of specific groups are viewed by outsiders. If that information is unfairly skewed, it unfairly skews outsiders' reactions when encountering members of specific social groups. And this is just an example that is more complex than what I'm making it to be only for simplification.