I think Grandpop enjoyed Judy Collins's take. Barbra Streisand recorded a version in the 80s which was very popular. Not surprising to you, I'm sure, Frank Sinatra's version is my favorite. He recorded it for 1973's Ol' Blue Eyes is Back, arranged by the great Gordon Jenkins, but I think Sinatra took it to another level when he sang it live, and there are a number of live recordings out there — it became a staple for him.
Interestingly, I read Bobby Short was the first to record it in a pop setting. I haven't heard that before, I'll be checking it out right after I'm done here. But I could imagine it being perfect for his unique voice and delivery.
At any rate, here's mine. I'm not sure I lived up to all of Sondheim's intricate instructions on how to deliver the lyrics, so hopefully he never finds himself down a rabbit hole on social media and comes across this. I assume he's got a lot of better things to do.