Oy, only five?
"Fragile" by Sting
First, Sting is my absolute favorite. I will not hear a bad word about him. Nothing Like the Sun is one of my "desert island" albums. At one time we owned it on vinyl, cassette and CD (the cassette is gone now). I'm including the original version here, but I also recommend watching this video from 9/11/01. Sting performed an intimate concert in Italy that evening; the rehearsals and preparation were filmed to be part of a concert film. When he learned of the tragic events, he offered to cancel the performance but all of the musicians still wanted to do it. This song became a kind of hymn after 9/11, and Sting performed it at the opening ceremonies of the 2002 Olympics in Salt Lake City.
"Walking on Sunshine" by Katrina and the Waves
A decidedly more uptempo piece than the first one (and the next one), this has stood firm as one of my all time favorite songs. It's just so damn happy!
Samuel Barber's "Adagio for Strings"
If you think you don't know this, you're probably wrong, as it's been used on soundtracks of movies and television shows. There is a choral version, which I also enjoy, but it's become a bit of a Good Friday tradition at church that the orchestra plays this and the choir just gets to close our eyes and listen.
"Some Nights" by fun.
OK, how about something from this century? I think I listened to this song 27 times in a row when I first heard it. I can't get enough of the tribal beat.
"Stars and the Moon" by Audra McDonald
I don't know how many years ago my friend David texted me and said "I have this song that you have to sing." It's become my signature song, with David at the piano. Sorry I don't have a recording of us - might have to work on that!