The musicals I have watched over and over again are Grease, The Sound of Music, and The Music Man. My grandmother introduced them to me when I was very young and they have always been my favorite. I enjoy musicals with a lot of songs you can sing along to and of course a lot of dancing. Other favorites include Carousel, South Pacific, Damn Yankees, and Bye Bye Birdie.
I also watch White Christmas and Holiday Inn every year at Christmas time. I started this tradition years ago and now my brother joins me as well and shares my love of musicals.