Christopher
I agree that The Dance is a good place to start...It was responsible for bringing in a new crop of fans and it also served as a 'wake up' for the 'older' fans that Fleetwood Mac were STILL here and better than ever.
Drawing from my experience, I was probably close to being a freshman in High School when I really became a fan of Stevie Nicks/Fleetwood Mac. I watched a Stevie Nicks concert on cable TV...it was from the Bella Donna Tour (I know there's a video/DVD out there and forgive my ignorance but I forget what it's called...my brother 'borrowed' my copy 7 years ago and I haven't had it since
)
The concert started off with Gold Dust Woman...and Stevie 'floated' out all bathed in soft light...in a beautiful midnight blue shawl....looking like an apparition...and from there it went into Gold and Braid...which was the first time I had heard this rare track...and it's one of my favorites to this day....and Stevie was dancing and smiling throughout this song and having such a ball...and looked so beautiful.....other songs in this include...Dreams, Sara, Rhiannon (for the encore) Edge of 17, Stop Draggin' My Heart Around...Outside The Rain...After seeing this I wanted to BE Stevie Nicks...
After that I went into Rumours and followed the whole 'soap opera' and 'drama' that went into recording that album....the music is SO intense on this album...It's facinating to hear such amazing art come from such heartache....
Let us know what your friend thinks!!
And good luck
BTW: I consider Other Side of The Mirror one of my favorites as well...recorded somewhere between post Betty Ford and pre-Klonopin...there was a glimpse of Stevie at one of her finest hours I believe...but that's just my 2 pennies