About Me

Hello,

Let me introduce myself, I'm the one and only Grand Daddy Cool as named by many of my friends and family. My actual name is Michael Charles Chessman and I've been in the entertainment business for 40 years and counting. I've been fortunate to share the stage with so many amazing performers over the decades and had the opportunity to meet some pretty incredible people along the way, many of which are now life time friends.
 As a visitor here you are becoming part of a fantastic community that has developed around me and the  the shows I'm so privileged to perform at. It seems every where I play people get together and seem to bond in some way creating a giant network of friends that participate in upcoming shows and public events. Its fantastic so see all these folks having fun and catching up with each other while enjoying the music and tales from the stage. I've learned a lot about people over the years and how to be a good conduit to a great time. No loud guitars and feedback is key and always play what people want to hear. I specialize in creating a fantastic vibe and try hard to engage my audiences creating moments and memories for all that attend.  I travel just about anywhere and my gear is the best in the industry providing a turn key, great sounding show every time with fast set up and load in. I'm a firm believer in that the less you see of me setting up before a show the better.  I don't intrude on your event anymore than I have too.       Working with my clients is a favorite part of the process. Seeing their vision of a successful & fun event come to life is always a treat. I bring a huge wealth of experience to the table and can help guide you through just about any theme or environment you'd like to create. I've done thousands of shows so I've seen a few things. I especially love playing solo acoustic shows where the name of the game is up close and intimate. There's nothing like connecting with an audience this way. To create or bring back special memories and feelings is an art and requires craftsmanship and work hard to get those moments at every show.  I really enjoy dinner shows, patio performances, back yard parties and small events as they are so personal and up close.  Its a special feeling when you can hear a pin drop in a break of a song because everyone is listening and deeply engaged. It's amazing!! 

  I've raised two beauty young women with the love of my life of 40 years and we're so happy to see them thrive and live the lives they worked so hard to build. Life has been good to us all. 

  Grand kids is the future for us and we are embracing our new place on this old planet with joy and optimism for the future. I still rock and roll like a 20 year old. I ride my Harley and atv along with my Ebike and just about anything else that moves me forward. I'm a rebel and always will be.  Age is just a number and I can go toe to toe with the youths any day. I can play all the new music should it be needed for your event but I like the classic hits best. The timeless, ageless tunes from music history always do well with any audience when performed well. I'm an old soul at heart.

  We spend a lot of time on the farm in Port Perry with my daughters and the animals, its a good life. 

  Music to me has always been just something I do but as I've got a little older I realize what a gift it's been and how lucky I am to be able to do this and make so many people happy while I have generally just have fun with crowds playing music and telling stories. Yes, its a lot of work sometimes but when it's good it's really good and I wouldn't trade it for anything. 

 My late Father said "we all get one good kick at the can" and I'm taking mine. I'm looking forward to the adventures in my life as I meet more people and explore new opportunities in music with new friends and old. It's a bright future and I hope in one way or another I can include you in the journey. We only get one  journey and I'd like you to be part of mine. 

  Connect with me on Facebook or Instagram at the links below and lets stay in touch and I hope to one day share a drink or conversation with you. I'd like to get to know you.

  Until the next time we speak or correspond I wish you well and good fortune. It's a great life so get out there and get some and with any luck I'm included in your path.

Thanks for dropping in and checking in on me.

Grand Daddy Cool