Leon Redbone was one of those characters that seemed to have stepped out of an E.L. Doctorow novel, or an Our Gang comedy. Playing Tin Pan Alley shuffles and ragtime ballads on the guitar and whistling like a drunken bum with just a swig of whiskey left in his flask. Except instead of appearing out of an alley in New York back in the roaring 30s, Redbone came from the Toronto folk scene and by 1975 had released his first album On The Track with Warner Brothers Records. He was a guest on Saturday Night Live twice their debut year, and impressed people as diverse as Bob Dylan, Bonnie Raitt, and Jack White.

Redbone went on to do voiceovers in commercials, did television show jingles(Mr. Belvedere), and even played a snowman in Elf. He recorded 16 albums between 1975 and 2014. Leon Redbone was this enigmatic character that never revealed his hand, and was even thought to have been a character being played by another celebrity, which  Andy Kauffman and Frank Zappa were both mentioned(he outlived both of them.)

My experience with Leon Redbone was much more personal. At 19-years old I bought his debut album On The Track. His television appearances in the 70s made an impact on me, and his voice and old-timey style stayed with me all those years. At 19-years old I saw a copy of On The Track in a bargain bin and instantly felt this melancholy nostalgia roll over me. I grabbed the CD and listened to it all the way home, which was an hour drive. Songs like “My Walking Stick”, “Lazybones”, and “Haunted House” were favorites. But it was Redbone’s timeless character that truly got me. Leon Redbone was a black and white character that stepped from a film short into a colorfully modern world, much like Jeff Daniels in The Purple Rose of Cairo. Except Redbone had the advantage of knowing the modern world, so his WC Fields schtick could somehow comment on the current times, all the while sipping his whiskey and singing Tin Pan Alley tunes. Whatever it was that he possessed, I completely locked into. He was like a cross between Foghorn Leghorn, Django Reindhardt, and Mark Twain.

In 2009 my older brother called me and told me Leon Redbone was playing at a local middle school auditorium on a Thursday evening in October. It seemed too bizarre to be true, so I looked into it and sure enough tickets were being sold for a one-time performance of Leon Redbone. He was playing on the same stage where I once performed in a trio my Junior year of high school. How could I not go to this? Turns out my older brother was equally affected by Redbone in the 70s, so we both got tickets and attended.

It was a strange and wonderful evening. Leon Redbone sat in an old chair on the stage with no lights on in the whole place except for a single living room lamp which sat on a nightstand next to Redbone’s chair. He bantered and told stories in a drunken drawl, and played all the songs I remembered as a kid. There were times I looked over to my brother to make sure this wasn’t just some weird dream I was having, and even for weeks after I’d mention it to him to make sure he indeed remembered that evening in October as well. He did. It was truly a one-of-a-kind and magical evening with Mr. Leon Redbone.

Leon Redbone died May 30th, 2019. He was 69.

RIP, Leon Redbone. Or, whoever you may have been.

Read his official obit here.

[youtube https://www.youtube.com/watch?v=cxNw1WAEvTE&w=560&h=315]