I love the 1988 albums from the Canadians, Leonard Cohen and Cowboy Junkies. The funny thing about the Cohen album is I think the songs actually sounded better when he played them live 20-25 years later, when he had a great band backing him. I saw him in 2012, one of my favorite concerts ever.
Also from 1988:
Mary Margaret O'Hara "Miss America"
Van Morrison and the Chieftains "Irish Heartbeat"
Billy Bragg "Workers Playtime"
The Proclaimers "Sunshine of Leith"
Fine Young Cannibals "The Raw and the Cooked"
Tracy Chapman "Tracy Chapman"
Waterboys "Fisherman's Blues"