The 4-disc SONGBOOK is a great suggestion. Those tracks span 4 decades of Lightfoot's career, so you'd get a fine sampling of his various sounds.
The 60s: youthful vocals; generally sparcer production.
The 70s (to about 82): richest, deepest vocals; lots of great production from Lenny Waronker.
The mid 80s to present: unexpectedly thin voice; but ultimately endearing, especially considering his burdens and longetivity.
I rate Sundown #1 of ALL the albums. Since you're already ranking it #3, I don't dare recommend where you go next. Maybe stay in the 70s for a while.
Wait. Let me muster some courage: get SHADOWS!
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