Cheers to Pat Dailey, the “Coolest SOB in the World”!

Pat Dailey, an island entertainer for forty years, summer resident, entrepreneur and island legend, passed away on July 3rd.

Pat was a seasoned entertainer before he ever heard of Put-in-Bay. He had traveled the country never knowing that a little island in Lake Erie would change his life and the lives of so many others.

He was new to the Cleveland area when friends there told him about Put-in-Bay. Pat’s arrival on the island scene came at a time Put-in-Bay was working to come out of its shell and become one of the top tourist destinations in the MidWest. He arrived on the island in 1978 when the island was still a bit sleepy with no Jet Express, no drive-on ferries, few hotels and little live entertainment. He soon became part of the island renaissance working with agent Tom Brady who was working with the island business community to promote Put-in-Bay at the time.

Interestingly, Pat’s first efforts to find a gig on the island were met with skepticism if anything at all. As the story goes, Pat was turned down at the Round House when he first came to the island. In retrospect, the venue could never have accommodated Pat’s explosion into Put-in-Bay’s entertainment world. Even Tip Niese at the Beer Barrel Saloon in the old Colonial building needed a little prodding to hire Pat, and it took a couple of meetings before Pat was hired to play his first gig. Pat told Tip he didn’t have to pay him anything, and that he would just take the door. With a house full of Westside Cleveland fans, Pat went on stage and ended up playing on the island for the next four decades before retiring in 2018.

Pat’s popularity had a phenomenal impact just at the right time, and soon “Pat Dailey” and “Put-in-Bay” seemed synonymous. His popularity spurred other bars to hire more and better entertainers leading to an entertainment revolution now fed with customers who could stay late thanks to the Jet Express or could stay overnight due to the building boom in overnight accommodations on the island.

In 1984, Pat headed to Key West. Playing at the world famous Sloppy Joe’s, he soon had a following there, too. A few songs and stories of Put-in-Bay and the Great Lakes had people spreading the word that Put-in-Bay was the “Key West of the North.” Put-in-Bay’s fame was spreading to the point that there has been a “Put-in-Bay Music Festival” in Key West for years featuring entertainers from the islands. It was also in Key West that Pat met the world famous poet, songwriter, playwright Shel Silverstein. Shel caught Pat’s show and suggested a songwriting collaboration until Shel’s untimely death 15 years later. Together they created “The Great Lakes Song,” “Blue Catawba Moon,” “On the Water,” “Walleye Willie,” “Vermilion,” “Ugly Feet” and more.

When the old Colonial burned to the ground in May of 1988, Pat, who had been staying upstairs in the employee housing there, lost his favorite guitars. Most everyone on the island was wondering what would come next and ultimately, Tip rebuilt. The Beer Barrel Saloon was now the longest bar in the world with a variety of really great entertainment for the huge venue, but with Pat always the main headliner with his songs about Put-in-Bay, the Great Lakes, life on the water, fishing and a variety of songs with clever lyrics every one of his fans could relate to, laugh at and have fun listening to.

While other entertainers sang the songs of others, Pat, aka “The Coolest SOB in the World,” “Legend of the Lake,” and “Jimmy Buffett of the North,” always played his own music creations….songs like “Put-in-Bay,” “Legend of the Lake”, “After the Fire,” ”Island Fever,” “Big Money Walleye,” “Yo Daddy,” ”Rich, Young, Dumb Nymphomaniac” and many more.
In 1990, Pat and his wife Anne became co-owners of Cooper’s Restaurant with partner Tim Matthews. Pat Dailey’s Tavern at the Bay. Pat’s family pitched in with his brother Dennis and sons Kevin and Tommy working there. Pat and Anne first had a small cottage in the woods and later purchased their island home on the South Shore where they also had a couple of rental cottages nearby.

With all this, Pat was ever community minded, whether performing with fellow island entertainers at the White Spider last ferry send offs at the Lime Kiln or at an island benefit. He was also gracious and welcoming to the many island friends he made over the years, plus a mentor to his fellow musicians who were making their way into the Put-in-Bay entertainment world.

In 2007, Pat left the Beer Barrel for a smaller, more intimate venue at The Boathouse. He played there until his retirement in 2018.

Pat’s rich legacy of original music isn’t his only one. Just ask island entertainers like Ray Fogg, one of the owners of the Reel Bar, about Pat’s influence on his life. Another one is Bob Gatewood, island entertainer and entrepreneur, who took Pat’s advice and moved to the island. Entertainer Pat Shepherd now entertains on the island with his Pat Dailey Tribute show. These and other entertainers will be playing on the island for years to come. Pat’s two sons, Kevin and Reese, still have connections to the islands. Reese plays here from time to time, and Kevin manages the Boathouse. Pat’s late son Tommy also worked on the island at the Brewery and Mojito Bay for many years. Scott Jackson, who worked at Dailey’s Tavern at the Bay in its second year in business, now owns and operates it as the Goat Soup and Whiskey and can thank the Daileys for the opportunity that dramatically changed his life. Also on an individual basis, Miller Boat Line captain Eric Engel’s life was enriched and influenced while moonlighting as Pat’s sound man for 20 years. It would take a book to tell the many positive experiences and stories of those whose lives he touched.

Pat’s legacy will leave an indelible mark on our Rock until the last day his “Put-in-Bay” song is sung. Rest in peace Pat, and thanks for the island memories from all your island friends and neighbors.