In 2005, CBC Radio had their listeners choose the best Canadian songs of all time.
Usually, these lists are pretty lame, but the CBC list has an amazing cross-section of music, and I personally believe all the songs should be there.
(I happen to agree with the choice of song for first place.
)
Given the fact that you are an Ian & Sylvia fan, I've put an asterisk after the songs I think would most appeal to you.
1. ‘Four Strong Winds' by Ian and Sylvia (1963) *
2. ‘If I Had $1000000” by the Barenaked Ladies (1992) *
3. ‘Heart of Gold' by Neil Young (1971) *
4. ‘Northwest Passage' by Stan Rogers (1981) *
5. ‘American Woman' by The Guess Who (1970)
6. ‘Canadian Railroad Trilogy' by Gordon Lightfoot (1967) *
7. ‘Both Sides Now' by Joni Mitchell (1969) *
8. ‘Suzanne' by Leonard Cohen (1967) *
9. ‘Big Yellow Taxi' by Joni Mitchell (1970) *
10. ‘Early Morning Rain' by Gordon Lightfoot (1966) *
11. ‘Lovers in a Dangerous Time' by Bruce Cockburn (1984) *
12. ‘The Hockey Song' by Stompin' Tom Connors (1973)
13. ‘Life is a Highway' by Tom Cochrane (1991)
14. ‘Try' by Blue Rodeo (1987) *
15. ‘The Weight' by The Band (1968) *
16. ‘New Orleans is Sinking” by The Tragically Hip (1989)
17. ‘Summer of '69' by Bryan Adams (1984)
18. ‘Takin' Care of Business' by Bachman-Turner Overdrive (1974)
19. ‘Snowbird' Anne Murray (1970) *
20. ‘Angel' by Sarah McLachlan (1997) *
21. ‘Constant Craving' by k.d. lang (1992) *
22. ‘Home for a Rest' by Spirit of the West (1990)
23. ‘These Eyes' by The Guess Who (1969) *
24. ‘Rockin' in the Free World' by Neil Young (1989)
25. ‘Sundown' by Gordon Lightfoot (1973) *
26. ‘The Universal Soldier' by Buffy Sainte-Marie (1964) *
27. ‘Courage' by the Tragically Hip (1992)
28. ‘You Oughta Know' by Alanis Morissette (1995)
29. ‘Wondering Where The Lions Are” by Bruce Cockburn (1979) *
30. ‘Mon Pays' by Gilles Vigneault (1965) *
31. ‘Raise a Little Hell' by Trooper (1978)
32. ‘Hasn't Hit Me Yet” Blue Rodeo (1993) *
33. 'Tom Sawyer' by Rush (1981)
34. ‘I'm Movin' On” by Hank Snow (1950)
35. ‘Echo Beach' by Martha and the Muffins (1980)
36. ‘The Safety Dance' by Men Without Hats (1982)
37. ‘Crabbuckit' K-OS (2004)
38. ‘High School Confidential' by Rough Trade (1980)
39. ‘Brother Down' Sam Roberts (2001)
40. ‘Diana' by Paul Anka (1957)
41. ‘Sonny's Dream' by The Wonderful Grand Band (1981) *
42. ‘Tower of Song' by Leonard Cohen (1988) *
43. ‘Sh-Boom (Life Could Be A Dream)' by the Crew Cuts (1954)
44. ‘Rise Up' by The Parachute Club (1983)
45. ‘Coax Me” by Sloan (1994)
46. ‘Let Your Backbone Slide' Maestro Fresh-Wes (1990)
47. ‘I'll Never Smile Again' by Ruth Lowe, performed by the Tommy Dorsey Orchestra (1940) *
48. “Fly By Night” by Rush (1975)
49. ‘Disco Sucks ' by D.O.A. (1978)
50. ‘My Swiss Moonlight Lullaby' by Wilf Carter (1933)