I can't speak for other cultures, but in general the typical American is pretty entitled. We live in an extremely individualistic culture where everyone thinks about their own happiness first. So when TRP claims that American women are extremely entitled, I tend to agree with them. However, I think this entitlement is even stronger in American men. Let me support my argument with specifics.

Men feel more entitled to higher salaries.

Now most people agree that when controlling for other variables such as career choice and time taken off work, the wage gap is much smaller than 77 cents on the dollar. It's more like 95 cents on the dollar. But what is the reason for this 5 cent difference? Women don't negotiate as well. Why? For the same amount of work, women believe that they are owed less than men do. Men feel entitled to more money, so they find it easier to negotiate higher salaries. There is nothing wrong with this of course, actually men have it right. They should fight for the most money that they can possibly get. However, my point is that men feel more entitled to more pay for the same amount of work than women. Source

Men feel more entitled to better grades for less effort.

A collection of students were asked how much they agree or disagree with statements of the following type.

"The instructor of this class should bend the rules for me"
"The instructor in this class should modify course requirements to help me."
"I should only be required to do a minimal amount of thinking to get an A in this class."
" I would confront the instructor in this class to argue about my grade. "

Men were reported to more strongly agree with these statements than women. To quote the article...

Thus, gender accounted for nearly all of the within-class and between-classes variances that previously existed in students’ entitlement beliefs. These findings suggest that men reported significantly more entitlement beliefs than women did, regardless of the classroom context.
Source.
Another study that found the same thing.
Another study that found the same thing, although the results were less significant.

Men feel more entitled to desirable mates.

Men are more likely to see dates with more desirable partners as their courtship entitlement; that is, they are more likely to put themselves forward as potential dates for my (fictive) ad placers when, an independent panel of judges determined, they would not be deemed sufficiently desirable partners for them. Source

Men score higher in general on narcissistic entitlement.

This gender difference remained stable in U.S. college student cohorts over time (from 1990 to 2013) and across different age groups. Study 1 also investigated gender differences in three facets of the Narcissistic Personality Inventory (NPI) to reveal that the narcissism gender difference is driven by the Exploitative/Entitlement facet..
Source

In addition, women are more likely to feel gratitude and forgive transgressions, which are both predictors of lower levels of entitlement.

Source 1
Source 2

I don't think that this gender difference is because we socialize men to be more entitled. Rather I think it is a biological result of men being more competitive in nature. Men need to compete with other men for mates and resources. This would go very badly for men if they were always deferring the object of competition to other more 'deserving' men. In order to compete, men need to believe that they deserve it. Entitlement is a natural result of this.