Seeing as your username is "Hairspray's Number One Fan," I have to say Hairspray's a lot of fun... and different live than the film. But if that's your username, then you might have already seen it.
Even if "Lion King" isn't exactly a true classic, I have to say, it's the type of show you won't be able to stop talking about after you see it, because it's very different from most musicals in terms of staging. I highly recommend everyone sees it live at least once! Just listening to the soundtrack feels weird because it's such an incredibly visual show. However, my mom didn't much like it-- it's much more African styled than the film, with a lot of African chanting and dancing, and she felt a bit alienated by that. I never thought a Disney musical could alienate anyone, but there you go.
Wanna Be A Foster suggested [title of show], but I have to warn that if you're not really familiar with theatre, that's not the way to go. There are a lot of injokes, and unless you're really involved with that type of thing, it might be hard to get. It'd certainly confuse my mom more than "The Lion King!"
Spamalot is AMAZING, but only great for true Monty Python fans. It's a rehashing of the HOly Grail, with a twist. It's actually my favourite musical (tied with Les Mis and Scarlet Pimpernel), and though there's a lot of crude humour, it's hilarious, the songs are catchy, and YES, Tom Deckman is just brilliant. If you think Spamalot is subversive, DON'T see Avenue Q, which makes Spamalot look like "The Little Mermaid!" Very, very inappropriate humour, but great.
Honestly, I really loved Little Mermaid, and that's a really fun, fluffy show, but it's hardly what you'd call a theatre classic. Definitely cheesy and over the top, but I can't remember ever having more fun in a theatre! Amazing cast, though, and if you go see it now, you'll still be able to see the OBC, which is not a common opportunity!
Two extremely popular shows are "Wicked" and "Phantom of the Opera." I've never seen either one live, but all of my friends who have loved them (Well, except for an unfortunate boy whose mother dragged him to Wicked. It is a rather girly show!)and both are packed with songs you won't stop singing for weeks afterward.
South Pacific and Gypsy are revivals of old classics, and they've been getting a lot of praise. Patti Lupone's a legend, and Kelli O'Hara's on her way there.
In my pants, she has burst like the music of angels, the light of the sun! --Marius Pantsmercy