The irony of progress
When a contemporary reader thinks of progress, they probably think of the evolution of philosophy from modernism to post-modernism as an instance of progress, but this book is Adorno and Horkheimer screaming from the mountain-top that actually, progress is one specific thing, not just the passage of time, not just "being cutting edge," but truly progressing as a species. For Adorno and Horkheimer, this obviously falls within the domain of ethics and the right answer is exposure to serious art and narrative.
The irony of tyranny
The irony of tyranny is implicit. Power derives from the people typically, but many times, tyrannical powers can find their way into power, and then they start changing policy so that they can stay in power. Therefore, a tyrant is ironic, because he has used the greatest platform for public service, and he has used it for his own selfish, regressive interests.
The irony of morality
This book captures an ironic aspect of morality, that even a person's sense of moral goodness can be manipulated by art with an agenda. The agenda of Western art for the masses is to make a good consumer. So part of the Westerner's view of what a happy, successful person looks like is to have the nicest, most competitive stuff. That's not a very ethical moral.
The irony of homogeneity in the arts
Art is about the diversity of the human experience, so it's ironic that the capitalist effect on art is that all the art starts to look the same. As the corporate interests learn more about human behavior and psychology, they can assure themselves profit by adjusting the art to match the formula that has been proven to earn money. So "art" declines into "entertainment" which declines into "blatant advertisement" or just propaganda.
The irony of power
People typically expect that the world is fair, but difficult, but actually, the truth is that a lot of the difficult in human life is only the consequence of a singular issue: Human greed. When people find power, they typically want to keep it, so instead of doing what is best for the people (helping others to learn business skills, helping others to start successful businesses) doesn't get done; only what keeps the status quo.