I'm a big Gordon Lightfoot fan myself. Amazon had a deal on all but his first four albums for 7.99 as mp3s, so i bought it and began enjoying his work tremendously. I would start one of three ways:
His first four albums are available as a double CD for 10 bucks. While I think his middle years stuff is the best, these first four are a great way to get started, and his first album is one of my favorites.
His greatest hits is a great 20 song set covering much of his career and lots of great, well-known songs. Can't go wrong with a smattering of a bit of everything, right?
If you want a specific album to start on, I think Sundown is his most famous, and has a bunch of great songs. I also think Sit Down Young Stranger would be good to start on (renamed to If You Could Read My Mind in the US)
Good luck plumbing Gord's gold :)
I only have two albums on my phone. I never figured out how get music on my iPhone via amazon and I HATE HATE HATE buying things from the iTunes store because they always end up disappearing later.
Hair in My Eyes Like a Highland Steer by Corb Lund
And some U2 album that I think came with my phone, but has some good songs.
The nuclear weapons guy in the office next door loaned me some Tegan and Sara and Oscar Peterson so I've been giving that a spin at work.
How about this? It's sort of black with orange and yellow and has 16 songs on it.
41 good songs. How can you go wrong with The Essential Willie Nelson. Although it's not just Willie, this is a really good album with Waylon Jennings.