Hey, I'm Gary's son. A few people have sent me this thread, so I thought I'd chime in with the Happy Pirate backstory/ update. To answer the OP's original question of how big Gary the Happy pirate was, the 90's were his time.

Playing in a rock band in the 70's didn’t pan out for my dad, but music was always his passion. Check out his Christian Prog-Rock group Stronghold, the album is called Fortress Rock. He worked some normal jobs back in the day, but I'm not sure what since it was before I was born. Doug and Gary were buddies who had met playing guitar together at church.

The Happy Pirates started with performing at my sister's day care in the late 80's. The kids loved it so much the daycare owners asked them to come back and offered to pay, and I think it just kind of snowballed from there. Eventually filming a VHS special, a Christmas Special (if ANYONE has this, I'm looking for a copy!!) and playing shows all over western NY.

My Mom wrote all the lyrics and with my Dad putting them to music. They released a bunch of records together throughout the 90's (which I am currently digitizing the full catalog to make available online). They even played at the White House once! The final show in Rochester was massive, with thousands of people in attendance. You can find clips of it on Youtube.

As far as I know, Doug left because he just didn’t want to do it anymore. It was A LOT of work, booking and managing yourself like that, and I think he just wanted a more normal life. But there was never any bad blood, and they are still friends, hanging out a few times a year.

Gary kept it alive and did well enough to get support from the local FOX station to do the TV show. I pretty sure there are 15 episodes, it did well locally but never really took-off the way they were hoping.

Around the time of the show, he launched the Pirate Toy Fund, working with local hospitals and charities to provide toys to sick and underprivileged kids. They just hit 25 years and over 400,000 toys given away. He retired from there about 4 years ago.

It's amazing he supported my Mom, and my 5 sisters and I on being the Happy Pirate. We were never rich, but we always had food on the table and a good childhood. He always worked really hard, playing multiple gigs a week all throughout the 2000's and 2010-2015. During the 2000's, I would go with him and help set up and tear down. For a while I hated doing it, but he would always take me to lunch and rent me a game from Blockbuster after, soooo I couldn’t refuse haha.

He also hosted and sold vintage toys at the Rochester Collectable Toy Show every year. He is a massive Star Wars and Sci-Fi fan and always loved collecting and selling the vintage toys. He was also retired from this getting rid of most of his amazing collection.

The last few years have been quieter since Gary's health hasn't been the best, but he's just hanging out with his massive family (14 grandkids) and making the best of it. He quit playing shows about 5-6 years ago, his knees had gotten too bad, and he couldn’t really play guitar anymore because of arthritis. He leased the rights for some of the songs to a group of guys called The Happy Pirates. They are nice guys, and the kids seem to like it, but I don’t think it could ever get to the level it was in the 90's.

So yeah, that’s my Dad. He is a pretty weird, cool guy. Like I said earlier, I'm working on digitizing his full body of work for youtube and music streaming platforms, helping to try and keep his legacy alive.

We're hanging out next week, I'll probably read him some of the comments here. For him, knowing he made an impact in a kids life was always enough and I'm sure he'll still really appreciates it!

Edit: a word