That's nice. Is he a country singer?
No, he is a Canadian indie rock singer. 
Has he ever toured in the U.S.?
Yes, all the time actually. I saw him live in Florida. 
How many times have you seen him live?
Only once a few years ago when I was 18. i want to see him more. I also like to watch his youtube channel.
Cool. I Let My Baby Stay one of his songs?
Yes, I really like that one because it is slow and peaceful. It helps me calm down.
I believe I saw him on The Tonight Show awhile back.
Yes, he performs on TV sometimes, but not recently since the borders have been weird.