Reddit mentions of Company

My recommendations are a bit limited because I haven't been to New York in many years, but from productions I've seen elsewhere or from previous casts, I'd recommend Wicked, Cabaret, and to a lesser extent Chicago. Wicked is what really drew me into musicals and it's a phenomenal extravaganza in terms of music and sets. I love gritty type musicals, and Cabaret has such a fun gritty atmosphere, it's very playful but very dark, and the ending left me stunned and speechless. Chicago is very fun and my mom who isn't into musicals, still talks about how much she enjoyed it years later.

Definitely the best way to experience theatre is live, but since I often can't, I watch a lot of cast recordings. The 2006 production of Company at the Lincoln Centre (it aired on PBS's Greats Performances), is my favourite. It's available on youtube or you can rent it from amazon. The first time I watched it, there were a couple of songs I found a bit boring, but over time, the more carefully I listened to it or had situations that made me relate to the feelings they convey, the more I love it.

I definitely agree with /u/ally-saurus's analogy. You get sucked in by a Harry Potter, and then find out there's such a wide variety of literature in the world, and generations of prolific authors. Maybe once you get into Hemingway or Shakespeare, you may find that you've outgrown some Harry Potter type books, but you'll likely still have a soft spot for it. I certainly found that I was first was drawn to the big, flashy productions but these days, smaller esoteric ones are what I prefer.