Hadestown might be a bit heady for someone’s first go-around at the theatre, especially because the ending is a bit bleak.
Wicked is a pretty good standard for a first show, and I think he might love Little Shop Of Horrors.
I also want to toss Waitress in the mix as well. I’ve always found it to be a very simple and accessible show with tuneful music, equal comic and dramatic moments, and just very easy to digest (no pun intended). I took my friend a few years back and he absolutely loved it as his first Broadway show.
If you think he might be into an improvised and audience-engaged experience, he might love Freestyle Love Supreme
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