Both Alex Trebek and Gordon Lightfoot were born in Canada, so I guess it makes sense their paths would have crossed professionally at some point. Here they are in 1963 on Music Hop, a teen dance show in Canada akin to American Bandstand. Trebek was its host. CBC: "In the interview, Trebek calls Lightfoot 'Gordie,' Lightfoot calls Trebek 'Al,' and Trebek hopes Lightfoot's upcoming songs 'turn out real well' for him. It's all very endearing." (Everlasting Blort)
If you don't want to watch it below through Twitter, head to the CBC site for this and more moments from Lightfoot's career.