Learned to be an Entertainer
Jack Wolf
Jack Wolf and his twin sister, who is nine minutes older, were born in Yuma, Arizona in 1987. Jack spent most of his early years growing up in East Tennessee, near Knoxville. His father performed in a Buck Owens cover band and loved to sing. In the 5th grade, he was formally introduced to music. He learned to read music he played piano and later played drums in school and church groups.
In middle school, Jack and eight others auditioned for choir but he was the only one not accepted. His vocals obviously have improved since then. Jack attended junior college in Fullerton, California for one year. At age 19, he had a crush on a neighbor who enjoyed the band Radiohead. With a guitar purchased at a pawn shop he taught himself a Radiohead song but the neighbor was unimpressed.
He later moved back to Knoxville and tried selling cars but hated the work. He began busking in Market Square, and made enough money playing guitar to get by. He loved it so much he’s been playing music ever since. He continued playing solo, became a dance instructor, even started writing songs.
Jack met Rob Cook at an open mike session. They began playing at a few local restaurants. Most of the gigs stopped in the winter so they decided to go somewhere warm to play. Someone suggested Key West “where Jimmy Buffett was from”. They spent three weeks working their way to Key West. Arriving in February 2013, they started busking and having a great time in the warm weather.
He met local Key West musicians and was quickly invited to play a few gigs. Jack and Rob Cook got a steady gig at Irish Kevin’s, working five days a week for the next eight months. Later, Rob moved on to the Love Lane Gang. Another friend, Tim Hollohan, called and suggested that Captain Tony’s needed a musician. Jack auditioned and was immediately hired in 2014. He played there six days a week for the next three years.
He loved playing music at Captain Tony’s where he learned to become a Key West entertainer. At first, he felt very vulnerable and hardly spoke to the audience while performing. He just played music and hoped he was appreciated. Later, he learned from others how to connect to his listeners. He said that if he knew how it affected his tips, he would have learned how to entertain the audience much earlier. He learned every song that was requested that he didn’t already know. For the next three years Jack increased his cover song list and honed those entertainment skills.
Wolf receives quite a few requests for Jimmy Buffett songs and has learned an appreciation of some of his amazing songs, especially the last song, “Bubbles Up”, which brings tears to his eyes. Probably because of Buffett’s influence, when writing a song, Jack prefers to write the lyrics first. He likes to work on the story then work on a melody.
He thinks Jack Johnson is one of the best songwriters who speaks of truth and love with a positive philosophy. His favorite Johnson songs are “Better Together”, “Banana Pancakes”, and “Flake”. He can play entire Jack Johnson albums. His favorite bands of all time are Nirvana and Sublime. In March of 2017 Jack was invited to perform several of his originals at the Sunday Ramble at the Key West Theater.
In 2020, during the COVID shutdown, Jack was worried that music would be cut and he would have to find something else to do. He quickly discovered how important music was. After his first online music streaming, he never felt more appreciated and respected. 
It changed the way he viewed his profession. He maintains a serious online presence with over 800 hundred subscribers and routinely releases music online.
Jack was immediately attracted to Kari Daley when they first met in 2013. They became very good friends and continued performing music as friends for several years. In November of 2020, Kari was living in an RV parked at Jack’s apartment driveway. She helped Jack decorate his first Christmas tree. Kari had a wedding gig next door and invited Jack to sit in with her. Something happened between the two during the gig. The bride asked if they were a couple. They became a couple that evening.
At a gig with Pete Jarvis and Kari at Sloppy Joe’s on May 3rd of 2021, as a diversion Pete started talking about Kari and Jack’s relationship. Jack got the engagement ring out, got down on one knee and proposed on stage in front of a roaring audience. Kari accepted and Pete cried.
Their relationship is very strong after three years. Once a month, they perform together as Wolf Love at Mangoes Restaurant. When they travel, they always perform together. Jack and Kari Wolf are an amazing Key West musical couple that have a lot of fans that love them both.
