Ever wanted to be a cowboy or sing the Ballads of the True West?

A great friend growing up had a dad in exile in Bahamas named Len Stuart, a larger than life businessman with crystal blue eyes. Len made a fortune in the bingo business and retired to Paradise Island. This was his jaw dropping spread and toys! 

I never knew Len when he was active in business but in his later years he was still a formidable man. Len was like a beloved general to his household and boat staff. Brilliant, a riot, and generous, Len could alternate hot and cold but was always engaging.

He became a co-owner of Second City Entertainment in the 1970s. I took my buddies to Second City Chicago for my stag this past year which was awesome. Len was an executive producer of SCTV and was with John Candy when he died on set of a Western in Durango, Mexico partying in 1994. The titan among comedians, Len became executor of Candy’s will.

Each night in retirement, after a few martinis, Len would fall asleep to old spaghetti Western movies on the TV. This man with everything may have only wanted to be a cowboy.  In the mornings Len would take his boats out fishing and would listen to music from country legend Willie Nelson.

Len passed away in 2016 after a brief bout with cancer and I think of him often. I’ve also been a big fan of Willie Nelson ever since.

“Texas in My Soul” a 1968 Nelson record I discovered is awesome.  Dallas, San Antonio, Hill Country Theme among favorites. “The Streets of Laredo” track 3 really had me in heaven. The story of a fallen cowboy Len would love.

“Go fetch me some water, a cool drink of water, to cool my parched lips,” the poor cowboy said. Before I returned, his spirit had left him. He’d gone to his maker. The cowboy was dead.”

Down the rabbit hole I found this Johnny Cash mono version from the 1965 record, “Sings the Ballads of the True West”  and was like, wow! Amazing range and storytelling by Cash. He’s just having fun with it.

"There is another more dear than a sister. She'll bitterly weep when she hears that I'm gone. And if some other man ever wins her affection, don't mention my name and my name will pass on."

"Take me to the green valley, lay the sod o'er me, I'm a young cowboy and I know I've done wrong."

The Streets of Laredo (mono) by Johnny Cash, for Len.