*Gold Diggers of 1935 *is an all time favorite. When the first number includes Ginger Rogers singing “We’re in the Money” in Pig Latin, you know you’re in for a treat.
Gilbert & Sullivan - The Mikado / Eric Idle, Lesley Garrett, Richard Van Allan, Felicity Palmer, Richard Angas, Bonaventura Bottone, Susan Bullock, English National Opera (1987)
An interesting and entertaining production of a classic, moved from Japan to an English seaside resort in the 1920s.
Oooh! Also, Guys and Dolls is great!
(Yes, yes, we all know Brando’s singing sucked.)
Singin’ in the Rain is a must. The acme of movie musicals.
The Music Man is very good on film since it had the same stage director as it had on Broadway (and Robert Preston).
For old ones, there’s Footlight Parade (Busby Berkeley, Harry Warren, and Jimmy Cagney) and 42nd Street (More Berkeley and Warren, plus surprisingly dark).
Chicago and Moulin Rouge are the best of the more recent musicals, but check out Woody Allen’s Everyone Says I Love You, an early entrant into the trend.
I absolutely love Hello Dolly (link goes to Netflix), with Barbara Streisand – who, no matter what anyone says, was the perfect choice for Dolly Levi.
Speaking of Barbara, I’ve also heard that Funny Girl is a very good musical, but I’ve never seen it.
Already mentioned but I definitely vote for Moulin Rouge, Chicago and My Fair Lady. Three of my favorite movies. I’m sure that you have seen The Wizard of Oz but I will mention it since no one else did. Meet Me In St. Louis was good in my opinion- but then again I think Judy Garland is just a wonderful creature, I enjoy anything she’s in. Re-reading the OP, I realize that you’ve likely seen all of these from your statements but if not, be sure to watch them.
Two that I think are quite important to the genre, and that haven’t been mentioned yet, are Porgy and Bess and Show Boat.
ETA: And you might get a kick out of a singing and dancing Clint Eastwood in Paint Your Wagon.
That’s from GD 1933. The number starts great, but it’s interrupted (by creditors). GD 1935 has “Lullaby of Broadway”.
Milos Forman’s version of Hair is fairly cool, if you don’t mind seeing Beverly D’Angleo’s boobs.
I tend to hate musicals, but I did like “Oliver”, along with “Man of La Mancha”.
Damn Yankees with Ray Walston as “Applegate”
It could help if you could share mini reviews with us of what you liked, thought was mediocre, not worth the time, etc.
Lots of people like Damn Yankees, but I found it to be somewhat blah overall. The creative musicals that I like include Black Orpheus with its (at least for me) almost hypnotic music. The Umbrellas of Cherbourg may be too intensely romantic for some tastes. It’s another musical that seriously stirred me. And a musical that can be seriously haunting is Hallelujah I’m a Bum, currently out in a DVD with a mediocre audio track (the VHS version was better). Maybe with the renewed interest in Jolson MGM will re-issue a better DVD, assuming that Criterion can’t/won’t.
If you like Busby Berkeley, then you could try Footlight Parade, with its fun, pre-code script and cast. Another fun pre-code is Love Me Tonight. Later fun includes some Doris Days, Calamity Jane and The Pajama Game, each with (for me anyway) lots of lively and memorable songs. If you like knock-your-socks-off singing, then Ethel Merman has several good numbers in Alexander’s Ragtime Band.
For what is not (yet) on DVD, Jessie Matthews made several enjoyably silly musicals, with perhaps It’s Love Again the best. Englewood Entertainment released some good-quality VHS tapes around the turn of the century.
There are many good musicals out there (some with Judy Garland). I hope that you have plenty of time to experience and enjoy them all. You gotta have heart.