Jeff Tupolski said: "I think if you had to narrow down a set of Sondheim’s biggest shows, it’d be a group of four rather than five. It feels like general consensus would include Sweeney, Woods, Company, and Sunday, while the fifth show would be more up for debate.
With that said, I do think Follies would be that fifth show, but the others feel solidly ahead, and there’s definitely argument for other works in its place."
Yes, I think you're correct. I had no trouble filling the first four slots, but deliberated quite a bit about the fifth. My personal favorite for #5 would be Assassins, but objectively, I think A Little Night Music is sort of perfect. Follies has a more thrilling score, but a less ironclad book in my opinion. Forum is also so well written that it's hard to mess up, but it's score is somewhat forgettable. Which is all to say, after you get past those first four, you could debate the merits of the rest for eternity.