MUSICIAN MICHAEL McCLOUD IS LEAVING KEY WEST AFTER 40 YEARS

a man holding a white dog in his arms
Musician Michael McCloud will leave Key West after 40 years. RALPH DE PALMA/ Contributed

By Ralph De Palma

If you’ve ever happened into Schooner Wharf Bar on basically any afternoon, you’ve seen and heard local troubadour Michael McCloud, who will be leaving Key West later this month after 40 years on the island. 

McCloud grew up in Beckley, West Virginia and early in his childhood decided he wanted to play music. His father was a “man of music,” but was not a musician. His mother was a piano player from Wales who sang in Welsh. At age 7, McCloud’s hands were too small for a guitar so he started playing a ukulele. It was at the start of the folk music era, inspired by the Kingston Trio. At 13, McCloud was playing folk music with his brother. 

At 17, he joined the Navy and trained as a hard hat diver. He played music in coffee houses all over the world. Completing his final Navy duty in Key West in 1970, McCloud promised himself he would return to the island.

He did just that 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 Buffett was a local “folk singer,” but was currently out of town. A neighbor, Mark Boudiansky (at the time, the food and beverage director at the Casa Marina) was standing in the front yard, introduced himself and asked McCloud what the guitar case was for. When McCloud told him, Boudiansky directed him a few blocks to the newly renovated Casa Marina and Bird Cage Lounge. McCloud was hired on the spot and his first gig was at 5 that afternoon. 

Boudiansky drove McCloud to the bus station to pick up his amplifier and PA system. On the way back, they stopped by Captain Tony’s Saloon. McCloud was introduced to the Captain, and Boudiansky asked if he had any day work for McCloud. Captain Tony said no, but walked McCloud across the street to Sloppy Joe’s and introduced him to Sidney Snelgrove, and said “Sid, I got your daytime musician for you.” In less than an hour, McCloud had met most of the Key West music scene proprietors and had two gigs. He performed at Sloppy Joe’s for 15 years and played the Casa Marina for nine years, playing double gigs nearly every day. Key West quickly became his home.

The first few years in Key West, McCloud 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 audiences were “cookie cutter” identical. The traveling gigs kept reminding him why he needed Key West: It was full of interesting characters and his audience was always different.

While traveling, he was hired to do a private party at the Rabinskis 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, McCloud 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 “Billie Jean” into a slow jazz swing beat. He gets a request for “Billie Jean” at least twice a week.

While performing, McCloud 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. 

McCloud 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 is “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 who got tired of playing the same old notes so they formed a new type of complex blues music and called it jazz. A little-known “Michael McCloud fact?” Jazz is his favorite music. He was a big fan of jazz fusion when it first started. He loved high energy rock ’n’ roll played by really good jazz musicians who wanted to rock like Pat Matheny and Jaco Pastorius. He says Joni Mitchell reinvented herself as a jazz fusion musician. “It was like when Bob Dylan showed up at the Newport Folk Festival with an electric guitar,” McCloud said.

Schooner Wharf Bar has been McCloud’s steady gig for over 30 years – a record for any Key West performer. “On those rainy days when the crowd is under the covered area at Schooner 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 it’s 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’ve 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 McCloud has become a Key West icon.

He 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. 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 on April 30. He will leave a huge hole in our Key West music tapestry.