Before the Baby Taylor was invented, and before the ukulele craze, a very young Tim Hollohan started out on the smallest instrument his dad could find him, a mandolin. By age seven he was performing alongside his dad and uncle in a band called Stain Glass Bluegrass. They played old gospel songs like ‘The Old Rugged Cross’ in an upbeat bluegrass style and performed in churches and at county fairs in South Carolina and Georgia.


As he got older, Tim was more interested in sports than guitar, until an ex-girlfriend encouraged him to start playing music in public. So in his mid-20’s he learned a bunch of Buffett covers and got his first gig at Cheeseburger In Paradise in Greenville, SC. One day they asked if he had a band for a Cinco de Mayo party and he said he did, but he didn’t. But what he did have is a family full of musicians, so he started a band called Sullivan’s Roof along with his brother, Sean Hollohan, and cousin, Robert Gunning the Fifth (aka Five Alive), and eventually his other cousin Andrew Gunning (now also a fulltime Key Wester). The band performed upbeat sing-a-long 90’s pop like Matchbox 20 and the Googoo Dolls.


While Tim played with the band a lot, he never thought he could really play music exclusively, so he still had a ‘day job’. After a whirlwind 24 hour visit to Key West he wound up landing a job at a building supply company in Monroe County and moved down in 2010. When he first got to Key West, he worked his ‘day job’ during the week and played music on the weekends. His first gigs were at Hog’s Breath and Willie T’s (before the stage and lighting).


Tim eventually quit his day job and began working 4-5 nights a week playing music, but with all the extra singing, he developed a vocal nodule and had to take time off. In retrospect it was the best thing that could have happened because he was able to start over and think about playing music more seriously.


Tim’s philosophy is simple: play songs that the audience wants to hear. When he’s not spending time with his wife and son, that’s just what he does. Tim can be seen out and about almost every day of the week at Willie T’s, Lazy Gecko, Hard Rock and Sloppy’s.