Oh, boy - do we ever envy you, starting from scratch, as it were. Anyway, the short answer is -- it depends. If money is no object, there's SONGBOOK, a 4 CD box set which runs chronologically through Gord's career. It's $54.99 new but you can get gently used copies for about $10 less.
Alternately, there's a 2 CD set, the UNITED ARTISTS COLLECTION, 49 songs covering his first four albums with UA before he signed with Warners (the 5th album for UA is SUNDAY CONCERT, his only - to date - completely live album.) The UA Collection is $10.99 at Amazon.com.
Or there's GORDON LIGHTFOOT - COMPLETE GREATEST HITS, a 20 song compilation with some from UA and some from Warners. I'm sure others will have suggestions (GORD'S GOLD and GORD'S GOLD II.) Many of us have favorite single albums as well (mine's DON QUIXOTE.)
As for your son, maybe Leonard Cohen, Bruce Cockburn, Ian Tyson, Tom (as in Stompin') Conners, Bryan Adams, Randy Bachman, Stan Rogers, Oscar Peterson, Hank Snow or Guy Lombardo, to name a few.
And if you have a daughter, there's Joni Mitchell, Ginette Reno, k.d. lang, Diane Dufresne, Diana Krall, Loreena McKennitt, Renée Claude, Amanda Marshall, Linda Lemay, Anne Murray, Monique Leyrac, Holly Cole, Diane Tell, Jann Arden, Buffy Sainte-Marie, Terri Clarke and Chantal Kreviazuk to choose from, along with Alanis Morrisette, Shania Twain and, of course, Celine Dion.
Jesse (Winchester) works for both.
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