My HS had a woeful tendency to do those shows written especially for schools. With titles like "Bats" and "How the West Was Warped"...the horror...
"We are engaged in two wars, one on drugs and one on terror, that can never be won. I mean, one is a group of inanimate objects and the other is an emotion. We might as well fight a war on pasta, which I guess the Atkins people are actually doing."
My school has recently performed Pippin, Grease, Fame and are now working on Dreamgirls. We tend to stray away from the Written-for-school shows because it is an arts high school specializing in drama and so far, I have nothing but good things to say about the shows. The dancing was especially good in Fame.
I wanted to get something that an "ex"-junkie like him would really appreciate and cherish....it's a brick of heroin shaped like a heart.
-Scrubs
In high school I did Annie, My Fair Lady, Grease and Joseph...Dreamcoat. Carousel is a great choice though, but you do need a Mr. Snow that's talented too...My college did that as our classic musical this year and it was amazing (and I personally hate the show but have gotten a little warmer) :-P
You need a musical with 2 female leads and 1 male lead, right? "Wonderful Town" fits those requirements exactly (Ruth, Eileen and Baker). "Chicago" would work as well (Roxie, Velma and Billy), but I don't really need to hear "All That Jazz" for the next decade or so. As other people suggested, you could also do "Gypsy." Going off the beaten HS path, you might also consider "Pal Joey."
When someone blunders, we say that he makes a misstep. Is it then not clear that all the ills of mankind, all the tragic misfortunes that fill our history books, all the political blunders, all the failures of the great leaders have arisen merely from a lack of skill in dancing. - Moliere