I'm going to give you the benefit of the doubt and assume these are sincere questions. If I'm wrong, please feel free to cruise on by. No hard feelings.
When Gruden writes, "Dumboriss Smith has lips the size of michellin tires," he is (whether consciously or subconsciously) playing on an ugly racial trope with significant, ignominious historical roots in this country. Unfortunately, there is a history in this country of making caricatures of black people with large, disfigured lips and exaggerated body parts, and which was particularly popular during Jim Crow. Throughout that era, the insensitive depictions of racial stereotypes of the "pickanninies," "coons," and "golliwog" dolls generally tended to include large, red lips in their depictions. (See
Link to the Jim Crow Museum's Webpage on Anti-Black Imagery). This is, shamefully, a very real part of American history. But these stereotypes continue to show up to this day, albeit typically in less obvious ways.
One example of how this sort of profiling based on stereotypical Afrocentric features (e.g., full lips, dark complexion, dark eyes, wide nose) can be particularly dangerous is its impact on our criminal justice system. Some studies have shown that while overt racial profiling in sentencing is down, profiling based on stereotypical Afrocentric features continues to be a problem (See
Link to One Such Study). In essence, a black man in America with a darker complexion and bigger lips is more likely to get a harsher sentence than a black man with a lighter complexion and thinner lips for a similar offense.
Your question about Julia Roberts is also interesting and illustrates these pervasive racial undertones as it relates to certain features. Julia Roberts tends to be celebrated for her full lips. And today, women across this country get injections and treatments in order to have full lips. However, African-American women with full lips have not generally had the same reception to their full lips, even fairly recently. (See
Link to NY Times Article re: Ugandan Model Aamito Lagum Getting Dragged By Racist Internet Trolls on Instagram). So Julia Roberts's full lips are something to be desired, but Aamito Lagum's full lips are vilified and the target of overt racial slurs, with the one major difference being the former is a white American actress and the latter is a black Ugandan model.
Back to Gruden, I can't say for certain whether he was consciously trying to be racially insensitive in his insult (which could be considered "racist") or whether he was simply trying to be crass and was merely unaware/ignorant of the racial connotation and undertones present in his comment (which I, personally, wouldn't consider "racist"). Intent is hard to judge off of an e-mail, and I try not to condemn people for the thoughtless things they say. But any time the discussion tends to the derogatory depiction or classification of a person's physical features that is also a historically, negatively stereotyped feature of that person's ethnic/racial group, I'm going to be suspicious, at the least.
Moving away from Afrocentric stereotypes, had Gruden said Josh Rosen has a nose like a flamingo, or that Younghoe Koo's eyes are more slanted than a Louisiana politician, would you ask whether Rosen really had a large nose, or whether Koo's eyes are actually slanted?
Just some food for thought (and, maybe, understanding).
