I would guess this has been done before.
Jesus Christ Superstar and The Wall come to mind.
I doubt I’ll ever adore a musical as much as Chess, and it’s criminally overlooked.
Chess In Concert: Live From Royal Albert Hall Trailer - YouTube Here’s a trailer for the best production of it, and really the first to even do the show justice.
Are you talking about movie musicals or musicals that originated on the stage?
Movies: It’s a cliche, but Singin’ in the Rain. Runners-up: The Band Wagon and On the Town.
Stage: Guys and Dolls. Runners-up: Parade and Avenue Q. Also, an honorable mention for Brigadoon. The show itself is soul-crushingly boring, but I love the music.
OK, now I totally want to see that. I’m too young to have caught Chess when it came out, and as you say, it’s underlooked, not often done and I’ve never heard of a production in my area in time to see it. 
I can’t answer this question. My backspace key is going to wear out if I keep trying and correcting myself.
The most I’ve ever enjoyed myself at a show? That’d be a local dinner theater production of Song and Dance (another underlooked one, IMHO.)
The one I’ve seen the most and spent the most money to see repeatedly in different cities? Les Mis.
The only one I loved enough to audition for at a professional level (and fail miserably, I knew I never had a shot, but I had to try)? Rent
Favorite musical made for movies? Moulin Rouge
Favorite movie production of a stage musical? The King and I
Favorite you’ve-never-heard-of-it musical? Hero
Favorite internet musical? Dr. Horrible’s Sing Along Blog
Favorite musical to be in? Jesus Christ Superstar …wait, no, Hair…wait, no, Grease …arrrgh!
Not really a fan of the form, honestly, but there will always be a soft spot in my heart for My Fair Lady–I saw it on TV as a little kid and fell in love and always will be.
Hard to choose just one, but for a stage musical, it’s currently The Drowsy Chaperone.
Movie is, of course, Singin’ in the Rain.
I can narrow it down to 3:
*Funny Girl
My Fair Lady
West Side Story
*
Toss-up between Hedwig and the Angry Inch or South Park: Bigger, Longer, and Uncut.
I don’t think of The Wall as a musical, and I’m going to keep right on not thinking it…otherwise that would make this question even harder!
Movie musicals, I’ve got a soft spot for the 1980’s version of Little Shop of Horrors (though I lived and breathed Grease for several of my formative years).
Stage musicals, I’ll give it to Book of Mormon at this time. I saw it last spring on Broadway, and I have the soundtrack on my iPod. Yes, I am working out at the gym to Hasa Diga Ebowai. 
The wife’s favorite Jesus Christ Superstar, closely followed by West Side Story. Mine is either The Music Man or Camelot.
Chess has a pretty convoluted history, as I understand it. I think it was originally performed just as a concert, not a fully-staged musical, and released on record. Then it was significantly changed and ran on Broadway. I remember reading that there are (or at some point were) competing interests between the two versions that keep it from being performed more.
I saw a touring production in 1990 that I rather liked.
I’ve seen five or six stage productions of Tommy, so I guess that would be my fave.
Does Rocky Horror Picture Show count? If so, that’s the one. If not, it would be my second favorite, Grease.
Cabaret…both stage and movie version - was quite good.
Chorus Line was great on Broadway, but the movie version sucked on every level and the producers of that film should be shot.
I have to say that **Wicked ** was the best musical I have ever seen.
I also love Joseph and the Amazing Technicolor Dreamcoatand Rent.
Has anyone ever seen Once? The song from the Tonys made me think I would really like it too.
I’m going to steal some of WhyNot’s breakout categories, for the same reason – no way to answer otherwise…
The most I’ve ever enjoyed myself at a show? Front row, Rent, NYC, when Idina Menzel gave me a wink during curtain call.
The one I’ve seen the most and spent the most money to see repeatedly in different cities? Les Miserables. Seen it in NYC, DC, San Francisco, Miami.
Favorite musical made for movies? Meet Me in St Louis. I can’t explain it. But I love this movie.
Favorite movie production of a stage musical? The Sound of Music.
Favorite you’ve-never-heard-of-it musical? The King of Hearts.
Favorite internet musical? Dr. Horrible’s Sing Along Blog
Favorite “old school” musical? My Fair Lady
Favorite tap musical? 42nd Street
Favorite general dance? West Side Story
Favorite musical to be in? Show Boat - I was Windy the riverboat pilot. Good role for me, since I sing in the key of ‘off’ and Windy has no musical numbers.
Musical season I’d produce and direct at the local dinner theater I buy after hitting the lottery:
Working
Sunday in the Park with George
The King of Hearts
Wicked
Avenue Q
Aspects of Love
Chess
It was a full stage production when I saw it in London, one week after the opening, but Misters Andersson/Ulvaeus/Price might very well have fiddled around with it after that (I don’t remember).
- West Side Story
- Tie: Guys & Dolls and 1776
- Chess (the UK cast recording version)
- Wicked
There are many other shows that I love, but these are the ones I’ve listened to the most over the years.
That’s my understanding, too. The performance in CyclopticXander’s link – in concert at the Royal Albert Hall – is supposedly Tim Rice’s ultimate version: it combines elements of the UK and US versions (and gave me an appreciation for Josh Groban’s voice that I didn’t have before), plus I think there’s some new stuff. It renders The American completely toothless, though, which makes me hate it. 
I can’t possibly pick just one! :eek:
Teen years: Camelot and West Side Story.
In my 20’s: Jesus Christ Superstar and Cabaret.
Well, that’s four, best I can winnow them down.
Overall favorite: West Side Story
Best “small” show: The Fantasticks
Most compelling characters/drama/dialog in a musical that also has good music: A Chorus Line
Best newish show: Spring Awakening
Best integration of all the elements of a musical into storytelling: Les Mis (particularly the first half… the second half degenerates somewhat into a sequence of soliloquies in song form, less interesting to me than the way the action moves from sequence to sequence so seamlessly in the first half)
Honorable mention: Rent