Singer-songwriter, actor, veteran, and lefty bon vivant Kris Kristofferson died earlier this week at the age of 88. The most important thing I have in common with Kris is that we’re both graduates of San Mateo High School. Go Bearcats.

This week’s Friday Cocktail Hour features Kristofferson’s most famous song, Me and Bobby McGee. Nashville mogul Fred Foster gets a writing credit for suggesting the title and theme of the song. The lyrics are pure Kris, “Freedom’s just another word for nothing left to lose.”

Roger Miller was the first to record Me and Bobby McGee, so that’s where we begin:

The songwriter recorded the song a year later:

Janis Joplin’s posthumously released version of the Kristofferson tune was a monster hit. It’s the main reason the song became such a classic. Thanks, Janis.

Me and Bobby McGee was recorded a gazillion times from 1971-1975. We move forward in time with this version recorded by my countrywoman Nana Mouskouri:

Here’s the good old Grateful Dead performing the Kristofferson classic. Jerry rarely introduced songs but I saw him dedicate this number to Janis:

Here’s a 21st Century recording by Dolly Parton with a little help from the songwriter:

Finally, The Highwaymen live:

What would the Friday Cocktail Hour be without a instrumental versions of the week’s tune? This time, Charlie McCoy followed by Chet Atkins:

That’s it for this week. I propose a toast to my fellow San Mateo High alum, Kris Kristofferson. Thanks for all the great music, movies, and stories. It’s what The Highwaymen would want. Never argue with Waylon, Johnny, Willie, and Kris.