Bert's Bar and Grill will have a special guest from Key West play twice this weekend for everyone's enjoyment.
Jack Pittorino, otherwise known as Yankee Jack, will perform Friday, July 27, at 7:30 p.m., and again on Sunday, July 29, at 2 p.m., in Matlacha.
The musician, who is originally from Boston, moved to Key West 24 years ago and now plays about eight gigs a week. Pittorino said he began playing in 1964 and did his first professional gig when he was 13-years-old.
While in Boston he said he was inducted into the Country Music Hall of Fame in Massachusetts and received more than 50 awards at the state, regional and national level.
Once he arrived in Key West his style gravitated to "trop rock," which is a cross between Alan Jackson and Jimmy Buffet with a little bit of Jeff Foxworthy thrown into the mix.
Pittorino currently has 11 albums released out of Key West and eight albums that he released while living in Boston. His first album that was released in the Keys was titled "Divorce in the Key of West."
That album, he said, consisted of a lot of content that was ex-wife bashing, which he said makes people think.
"It's not blatant, it is innuendo," he said about the type of humor that has made his career successful.
His inspiration comes from everything and his music is geared towards the audience. While playing a gig, Pittorino said he takes in a scenario that pops up, which may be marriage, divorce, an engagement or someone meeting someone else for the first time.
"I try to have a song that covers it," he said of his music.
If any of those situations are taken out of context, Pittorino said it may be of bad taste, but when doing it within a theme and certain flow and flavor everything seems to work out.
This weekend, he said he will put his feelers out while entertaining the crowd to see if he has permission to sing some original songs and if the crowd enjoys the music he will sing more. If not, he said he will entertain the crowd with music by some well known musicians.
"You have to make an informed decision by looking at them," Pittorino said of which songs he will sing. "If there is an audience with kids, you do a children's show. I can adapt to any kind of venue."
Although he has never visited Matlacha or Pine Island, he said he and his wife visit Fort Myers Beach whenever they have the opportunity.
"Fort Myers Beach seems to be a perfect place for us," Pittorino said, adding that if they ever have a few extra bucks they would purchase a condo on the beach.
He said he is looking forward to playing at Bert's.
"Everyone knows Bert's," he said. "People say they go there all the time."
Due to the popularity of Bert's, Pittorino said he is expecting a pretty good house.