The usage of the phrase has evolved past carrying about the actual generation (kind of like how people still talk about "millennials" like they're college students).
Also, Hoffman very intentionally opened the door to talking about generational differences, this kind of feels like the commenter may have touched a nerve
"Ok boomer", as I understand it, basically means "I'm not going to engage seriously with that outdated perspective", often used to shut down a conversation rather than to continue it.
I don't know that what Reid is expressing is an outdated perspective, but that's of course subjective.
The usage of the phrase has evolved into a thought terminating cliche.
> kind of like how people still talk about "millennials" like they're college students
Is that really an evolution? "Millennial" was coined to refer to the cohort that gradated from high school in the year 2000. Not all high school graduates become college students, of course, but if we are generalizing it isn't unreasonable to think of recent high school graduates as college students.
Now, there was nothing in the definition to declare if you must continue to recognize them for who they are going forward (i.e. 40-somethings now), or if you are to remember them in that moment as high school graduates, many of whom were college bound. So still thinking of "millennials" as being college students is a fair interpretation before evolution.