*1943*
- At age five, he makes his performing debut, singing I'm A Little Teapot at St. Paul's United Church Sunday School in Orillia.

*1948*
- Lightfoot cuts his first record.  His sister Bev accompanies him on piano and they get it on the first take.  The school principal plays the record over the school's PA on parent's day.

*1950*
- Lightfoot begins piano lessons and voice study under Ray Williams in Orillia.
- The ten year old Lightfoot wins second place in an amateur show at the Orillia Opera House, sponsored by a local radio station. He sang "Bless This House".

*1951*
- Lightfoot makes a 78 rpm record of "The Lord's Prayer."
- Wins first place in his under 13 vocal class at the Toronto Kiwanis Festival, singing Alpine Song and Under The Greenwood Tree. He finished third in the unchanged voices class.

*1952*
- Wins first place again at the Toronto Kiwanis Festival in the soprano unchanged voices class.  He made his first appearance on the Massey Hall stage that year where he sang his winning performance, a 19th century song called "Who is Sylvia". (Read More...)

*1954*
- He makes his network radio debut, singing with a group called the Teen Timers.

*1955*
- Lightfoot writes his first song.  It's a topical song titled, The Hula Hoop Song.  He presents it to a publisher in Toronto and while it wasn't accepted, he received encouragement and the rest, as they say, is history!

*1956*
- His barbershop quartet finishes second in an Ontario competition.