Leon Redbone. I hope I’m this cool when I’m old. Leon Redbone is like the grandfather you wish you had. He tells little cute, schtick-y jokes all the time, and is basically constantly entertaining. And he is the only guy out there I know of who seems like a true ambassador of the Delta Blues / Tin Pan Alley eras. He plays a mean guitar and his voice is perfect for the songs he sings. None of it seems phony or put-on.
Something you might not know about Leon Redbone: he was the voice of the snowman, Leon, in the Will Ferrell movie Elf, and he sings the “Baby It’s Cold Outside” duet with Zooey Deschanel that plays over the end credits.
I’ll leave you with one of the jokes Leon Redbone told: “My doctor told me to drink alcohol an hour before I went to bed.” Someone in the audience says, “What happened?” Redbone says, “I tried but I could only drink for 45 minutes and couldn’t hold any more.” Ba-dump.
When I grow up I want to be Leon Redbone.