One is easier than five for me.
Camino (album/c.d./whatever) by Oliver Schroer
Why? the music itself. The story of the journey. The memory of the concert at Trinity-St. Paul. Trying to imagine what he'd be writing/playing now if he hadn't died so young. Simply the music.
To fill out the other four spots.
Why? the music, the musicians - the stories of how they came to Canada - how they make me laugh/dance/sing/appreciate the sheer musicianship. The rhythms/tonal combos that were outside of my Eurocentric experience growing up. Appreciating that white men aren't necessarily the be-all, end-all musically. They're damn good individually and collectively.
Why? the combination of the orchestra and the soloist. I like, don't love, Vivaldi. However, Anner Bylsma takes just about everything he touches over the top for me. Tafelmusik, with Jeanne Lamon at the lead, was at its youthful peak then. There is a group of new musicians livening things up again now - but the early 1990's were an exciting time to go to their concerts.
Why? sheer beauty and simplicity of his voice. Simplicity of the arrangements on most of this.
Roly Poly by Asleep at the Wheel, featuring the Dixie Chicks. From the Ride with Bob disc.
Two of my favourite contemporary groups, playing music originally made popular by one of the best Texas Swing bands. Joy and musicality. Pretty unbeatable combo.
I don't need sturm and drang.