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A chat on subreddit /r/NoStupidQuestions
human
A pint would equal 5 Manhattans or old fashioneds. Or roughly equivalent to a 12pack of light beer

I've done that numerous times throughout my life, but usually only on a Friday Saturday night when I was in my 20s

That's a lot in one sitting. Especially if you double it.
gpt
You must like a heavy pour. Old fashioneds are normally made with two ounces of 80 proof alcohol, Manhattans with 2.25 ounces. A pint is 16 ounces so a pint would equal eight Old fashioneds or over seven Manhattans.

Light beer contains the equivalent of one ounce of alcohol so a pint equals 16 light beers.