Michael McCloud – Leaving Key West after 40 years.

Comments: 42

Michael McCloud – a plethora of useless information

Michael McCloud and his faithful and Cinderella performed at Schooner Wharf

Michael McCloud grew up in Beckley West Virginia and decided he wanted to play music very early in childhood. His father was a man of music, but he was not a musician. His Grandmother was a piano player from Wales, she sang in Welsh. Early on his hands were too small for a guitar so he started playing a ukulele at seven. It was at the start of the folk music era (inspired by the Kingston Trio). At thirteen he was playing folk music with his brother.

At seventeen Michael McCloud joined the Navy, trained as a hard hat diver, played music in Coffee Houses all over the world, did his final Navy duty in Key West in 1970. After the Navy he promised himself to return to Key West.

He returned in 1971, telling the cab driver he was a folk singer. The driver drove him past the house where Jimmy Buffett was living, telling him that Buffett was a local “folk singer” but was currently out of town. A neighbor Mark Boudiansky (Food & Beverage Director, Casa Marina) was standing in the front yard, introduced himself, asked Michael what that guitar case he was holding was for? When Michael told him, Mark directed him a few blocks to the newly renovated Casa Marina and the basement “Bird Cage” lounge. He hired Michael on the spot and his first gig was 5 pm that afternoon.

Mark drove Michael to the Greyhound Bus station to pick up his amplifier and PA system. On the way back, they stopped by Captain Tony’s on Green Street. He was introduced to the Captain and Mark asked if he had any day work for Michael. Captain Tony said no but walked Michael McCloud across the street to Sloppy Joes and introduced Michael to Sidney Snelgrove and said “Sid, I got your daytime musician for you.” In less than an hour Michael McCloud had met most of the Key West music scene proprietors and had two gigs. Michael performed at Sloppy Joes for fifteen years and played the Casa Marina for nine years playing double gigs almost every day. Key West quickly became his new found home.

The first few years in Key West, Michael traveled for gigs. He traveled to music festivals and performed as a backup singer for a group of singer-songwriters. The gigs were terrible and the audience were ‘cookie cut’ identical. The traveling gigs kept reminding him of why he needed Key West. Key West was full of interesting characters, and his audience was always different.

While traveling, he was hired to do a private party at the Rabinski’s in the suburbs of Baltimore for an After-Circumcision party.  He planned to sing a few of the classics, some jazz tunes, but needed a blues song – he found Big Joe Williams, “Take A Little Off the Top”.

Lately, Michael has taken songs that everyone knows – but not the way Michael McCloud knows them – and makes them great fun. For example, he turns Michael Jackson’s “Billy Jean” into a slow jazz swing beat. He gets a request for “Billy Jean” at least twice a week.

While performing he never takes his mind off the audience and always appears completely comfortable. On a good day he gets requests for really good songs that he hasn’t played in so long they’re hard to remember.

Michael says while performing at any point in time, “I’m playing music for three groups of people.” One group can only hear the beat – they could dance to the National Anthem. Another group thinks they know the song but only really know a few chords of music and three or four words of the chorus. The third group, they know what you’re doing and are zoned in. The first group, the largest, listens “at” music. The second group listens “to” the music. The third group are “into” the music and the artist. Most from group one are young and the music is only incidental. Group two are in their middle years and probably really intended to listen to the music. Group three are usually in their older years, and they know what they’re there for.

According to the McCloud philosophy Jazz came from a bunch of Blues players that got tired of the playing same old notes and they got together and formed a new type of complex Blues music and called it Jazz. Michael was a big fan of Jazz Fusion when it first started. He loved high energy Rock n Roll played by really good jazz musicians that wanted to rock like Pat Matheny, Joco Pastorius. Joni Mitchel reinvented herself as a Jazz Fusion musicians. Michael says “it was like when Bob Dylan showed up at the Newport Folk Festival with an electric guitar.”

Schooner Wharf Bar has been Michael McCloud’s steady gig for over 30 years – a record for any Key West performer. Michael said, “On those rainy days when the crowd is under the covered area at Schooners Wharf and I’m on the stage playing just whatever the hell I want. I get to really listen to the way I sound and its fun.”

McCloud says he tries hard to be honest with himself but not everyone else. He says, “I’m a plethora of useless information. I’m not very proud of most of the things that I had done in my life. Most of the things that I’m proud of doing in my life, I made up.” From these and many other comments, one can understand how Michael McCloud has become a Key West icon.

Michael likes Key West because it is a destination. You have to want to arrive here when you come to Key West. It’s at the end of the road. He says, “In Key West, there are very few people that are in a bad mood because they’re late getting to where they wanted to be.” Michael McCloud will retire to Arizona this April 30. He will leave a huge hole in our Key West music tapestry.

I have nine of his recorded albums and I know I’m missing a few. He worked with Shel Silverstein for over 15 years producing hundreds of demos and new arrangements. He performs to thousands of adoring fans that will never forget him. No Key West musician has ever held a steady gig longer than his 31 years at Schooner Wharf.

In spite of his humor Michael McCloud has plenty of accomplishments to be proud of – and he has plenty of information that is very useful… and he had the cutest little doggie ever.

Authors Footnote: Michael McCloud refused all attempts to be interviewed for the Soul of Key West, Volume I & II. In fact I don’t remember any articles or interviews of Michael by anyone in Key West. It seemed like he was in the Key West Musicians Witness Protection Program. One afternoon in 2017 while attending “Friday Church” at Schooners, while on a break Michael came over and asked out of the blue “When are you going to interview me?”

I immediately scheduled an interview before he changed his mind. I have now interviewed 146 Key West musicians and write a weekly music column for the Key West Citizen. My interviews usually last 30-40 minutes. Michael’s interview lasted 2.5 hours one side of my ribs hurt from laughing so hard. The above is a small slice of his so called “useless information”.

I have an entire section of Michael and Shel Silerstein collaborations. I’ll squeeze it all into the next release of the Soul of Key West, Volume III. Coming in the fall of 2023 available on this website and most book stores and gift shops in Key West.





  • Anita Davis says:

    I heard Michael back in the day at Sloppys! Bought his tape!

    • Nancy Fischer says:

      Micheal sending much love, laughs and joy within your sails.you charmed us and may you fondly remember the backyard BBQ twirl girl.here he comes darlindaughter:)×0

      • Terri says:

        My husband, friends and myself have been entertained many times by the amazing Michael McCloud. We count ourselves lucky to be a part of his history. Thanks for end memories. Enjoy retirement. You’ve earned it! ❤️🌴🐚

        • Doug Mogle says:

          A few years ago I showed Michael a 35 yr old cassette tape I had bought from him when he was still working at Sloppy’s. In classic Michael fashion he shrugged his shoulders totally unimpressed. Well Michael I’ve impressed by you for many years. Happy trails!

      • Mark Budiansky says:

        Michael you might be leaving but you’ll never be gone 😎

        • Sue and Phil Dean says:

          We’ve been following Michael since he played at The Bull. We used to travel from St. Lou to KW for a week every month. We were regulars. Never tire of his patter and songs.

    • Terri says:

      My husband, friends and myself have been entertained many times by the amazing Michael McCloud. We count ourselves lucky to be a part of his history. Thanks for the memories. Enjoy retirement. You’ve earned it! ❤️🌴🐚

      • Jae Side says:

        I’ve been playing at The Marker Resort on Sundays since I moved here 10 months ago, and go over to Schooners on my breaks to listin to him. I didn’t know who he was at first, but the more I listened to him, and heard his stories, I realized how much of a legend he was. This piece here has helped me gain a way better understanding of his story,so thank you! I had to go down and catch him today since it might rain tomorrow. Much Respect to both of y’all 🙏

    • Jeff Lee says:

      I had the pleasure of seeing him in the 80’s at the Bull. I was hooked. Key West won’t be the same without him. Much love Michael in your next chapter.

      • Cindy Kapellusch says:

        For 24 years we were entertained by Michael McCloud! Excellent musician.. enjoy your retirement sir.. you earned it! I’m coming back as a Schooner Wharf Dog💕

  • Charles Norton says:

    A true legend and amazing singer!!

  • Jason Curtis says:

    I love this and Thank you both for putting this together 🙂
    I ended up with one of Michael’s guitars by an odd coincidence and the instrument and the man are both always an inspiration. He will be truly missed.

    • Elizabeth Shewan says:

      My late fiancee,Scott Strong had a wonderful memory of riding in the back of Michael’s bike while handing out “ugly shirts” to needy guys,!!!

  • Ronnie Sites says:

    Can’t wait to hear the “rest of the story “

  • Dave Cox says:

    Love This!!!!

    • Bob George says:

      It has been many years since Micheal strolled into then Rum Runners on Duval to play a few songs in between sets of the duo that was there. He played
      “Just came down for the weekend” and “Conch Republic Song”. He said he was playing at Bull and Whistle down the street. I have never forgot about this 1st introduction to his music. I wish Micheal all the best in his retirement!!

  • Sarah says:

    Heard him many many times over the years. Wonderful musician, an icon of KW

  • Russell Roman says:

    Been going to KW since 1998, when we got married.Now we travel there at least 6 times a yr. Michael has always been part of our daily walks. He will be truly missed at that ” Tourist Town Bar”. And Yes we are the ones that Just came down for a weekend…25 yrs ago.

  • Papa Tom Grizzard says:

    Linda and I were just there and so happy to see Michael before he leaves. Been going there for 23 years

  • Emily Wright says:

    Dont go…… !

    • Kelly Sommerkamp says:

      I found Michael on my first trip to KW to visit my Das who had moved there. He was going on about this musician’s sarcastic humor. Once I heard him I was hooked. My son was 4 at the time, we returned when my son turned 21 and we are still huge fans. Michael you will be missed my friend!

  • Jeremiah Arney says:

    Thank You for all the great music we heard when we traveled to Key West. I’ve got a few of your CD’S to remember your music.

  • Bob S says:

    Saw Michael twice two weeks ago. He will leave a huge hole in the music scene. A heart felt thanks for your music we’ve enjoyed it since 1996. Enjoy Arizona.

  • Connie Thurnher says:

    First heard Michael at Schooner Wharf in 1993, I was there with Island Boy Band from Tidewater Va. playing at Margaritaville. I was ‘hooked’ on Michael McCloud! Each cost to Key West my first mission was to hear Michael play. Happy to say I have all of his CD’s, signed. Fair Winds Michael on your new adventure. Needless to say Key West won’t be the same without you🤗

  • Richard H Besser AKA Rick Banyan says:

    We came to KW sometime in the late 80’s for 2 week vacations, then 3 week vacations and then spending the entire winter there. Michael McCloud and the Schooner Wharf has always been an integral part of our enjoyment while being in Key Weird. Thanks for all the fun music and banter Mr. McCloud.

  • Lynda Bradeen says:

    Michael is like a brother to me….While living in Key Largo my husband & I made many a day trip to Key West just to sit & listen to Michael til 5pm then go back to Key Largo. I have introduced Mike & his music & band of happy-go-luckies to countless friends over the years. He will be sorely missed but our loss is Arizona’s gain. God speed Michael & know you take a piece of our hearts with you….This “tourist” loves you.

  • It’s sad to see Michael go. He was the best songwriter in town.

  • Denise and Bruce Canedy says:

    You’re one of the reasons we love KW. An older couple into the “music” God speed to your next adventures. You will be missed.

  • Steve Fowler says:

    The wife and I have been coming to Key West since 2000. We never missed a year not seeing Michael play. I have downloaded some of his songs from Apple music. I hope you enjoy Arizona as much as you have enjoyed Key West!

  • Lawrence Talt says:

    I loved hearing you sing “She got a Butt”. Thanks for the music!

  • Mark Budiansky says:

    Michael might be leaving, but he’ll never go away 😎

  • Vicky Barnes says:

    Thanks for the memories of entertaining chatter, while waiting to start the next song. Loved sitting and listening. Good luck in Arizona and retirement.

  • Mark Budiansky says:

    Gone but not forgotten😎


    We have followed MM since we went to Key West on our honeymoon 32 years ago! We will miss him at Schooner Wharf. What a loss for us but I can imagine he is ready to slow down. All the best in AZ

  • Howie Baker says:

    Michael has been a delight and an inspiration in a world that takes itself way too seriously. He’ll keep entertaining through his recordings. Thanks.

  • Joe Seagle says:

    Sorry to hear Michael has finally retired and left KW. My wife and I have enjoyed his music and banter since the late 80’s (Sloppy Joe’s, The Bull, SWB). Our planned trip to KW this year will not be the same… another “last little piece of old KW” is gone. Best wishes in your retirement, Michael!

  • Jay W Wright says:

    Sorry to see him go. We go to Key West every year and always made it a point to hit SWB to hear him sing. I always requested the Dutchman and he always sang it to perfection. Best of luck to him.

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