To me it feels like...
Early 2000s Apple vs MS/Dell/then later Samsung/everyone else (even on some superficial counts, e.g. recent ads).
The better balanced Democratic Party of past vs the now pretentious/deluded/self-destructive Party.
Some corners of IRC/90s security underground vs the holier-than-thou Institution (many of the 90s legends are at OpenAI now).
Anthropic continues to reflect much of what went wrong with the Democratic Party...elitism, insulation, naivete (both morally and strategically), etc.
OpenAI's culture is far more approachable than Anthropic's, similar to certain periods of Apple vs Microsoft (IMO). And the culture is more conducive to potential innovation on the next-most important layer(s). The product strategy is (more) astutely multi-pronged and balanced, again IMO.
Even OpenAI's design and messaging/communication are much more approachable/interpersonal than Anthropic's, specifically with regard to yanno...the rest of the normal world vs devs/researchers/technical/corporate folks.
Yo OpenAI vs Anthropic is literally this generation Windows vs Mac