Heart of a Fool (original song)
My Poor Heart (original song)
Everything (original song)
Regionally renown for his smooth yet powerful voice and impressive guitar abilities. Will Cheshier is known for his performances of classic and contemporary hits as well as a collection of distinctive and soulful original tunes. Far from a coffee house strummer, Will’s voice and acoustic guitar arrangements of popular favorites have a full sound without being overwhelming.
Will can provide up to 4 hours of uninterrupted (no breaks) performance that includes hits from Marvin Gaye, The Beatles, Bill Withers, Micheal Jackson, U2, John Mayer, Dave Matthews, Keith Urban and many others.
11 reviews
Martin B.
October 3, 2026Our guests could not have been happier with Will Cheshier! He was the perfect entertainer for our Friday evening dinner and exactly what we were looking for. Will is an exceptionally talented guitarist with a wonderful voice and an impressive variety of music spanning multiple genres.
From start to finish, he was a pleasure to work with. He arrived early, was extremely polite and accommodating, professionally dressed, and understood the room perfectly. The volume was spot-on throughout the evening - not a single comment about the music being too loud or too soft, which is no small accomplishment in a club dining environment!
Will helped create exactly the atmosphere we wanted, and the feedback from our members and guests was outstanding. On a five-star scale, Will Cheshier gets six stars from us! We look forward to having him back.
Hired as: Singing Guitarist
Danielle D.
July 31, 2025Very polite and easy to work with! Our membership had a great time!
Hired as: Singing Guitarist
Angela S.
June 28, 2024Will was so great at our party in the flats! He was the perfect addition and just the right volume. He played songs we all know and love and even a few requests! I couldn’t have been happier with his performance! He is an awesome musician and has an incredible voice. I only wish I had more parties to book Will.
Hired as: Singing Guitarist
Will Cheshier
It was a pleasure to meet you and perform for your wonderful family. Congratulations the new couple!
Kelly R.
May 31, 2024Will played great music, was on time, professional and did a wonderful job for us at our event. Would highly recommend him for future events.
Hired as: Singing Guitarist
Kara M.
October 8, 2023Will helped create the perfect environment for our gathering. He was communicative leading up to the event, arrived early and sounded great!! We will certainly call Will again!
Hired as: Singer/Songwriter
Friday
Dinner Party
5:00pm - 8:00pm
•
Beachwood, OH
Friday
Dinner Party
5:00pm - 8:00pm
•
Shaker Heights, OH
Friday
Dinner Party
5:00pm - 8:00pm
•
Shaker Heights, OH
Friday
Dinner Party
5:00pm - 8:00pm
•
Shaker Heights, OH
Saturday
Camp Event
6:00pm - 9:00pm
•
Lakeside Marblehead, OH
Thursday
Corporate Event
4:00pm - 7:00pm
•
Cleveland, OH
Thursday
Restaurant/Bar Event
6:30pm - 8:30pm
•
Columbia Station, OH
Friday
Nonprofit Event
5:00pm - 6:30pm
•
Cleveland, OH
Saturday
Wedding Cocktail Hour
5:30pm - 8:30pm
•
Cleveland, OH
Thursday
Nonprofit Event
4:30pm - 7:30pm
•
Cleveland, OH
Thursday
Dinner Party
6:00pm - 8:00pm
•
Cleveland, OH
Sunday
House Party
4:00pm - 8:00pm
•
Sandusky, OH
Saturday
Cocktail Party
5:30pm - 8:30pm
•
Huron, OH
Saturday
House Party
6:00pm - 9:00pm
•
Cleveland, OH
Saturday
Concert
4:00pm - 7:00pm
•
Cleveland, OH
Friday
Dinner Party
6:30pm - 9:30pm
•
Bay Village, OH
Thursday
Concert
6:00pm - 8:00pm
•
Cleveland, OH
Saturday
Cocktail Party
6:00pm - 10:00pm
•
Avon Lake, OH
Saturday
Graduation
5:30pm - 9:00pm
•
Solon, OH
Saturday
Grand Opening
10:00am - 2:00pm
•
Mentor, OH
Saturday
Birthday Party
6:00pm - 9:30pm
•
Strongsville, OH
1 grounded outlet
Singing Guitarist