Phil McKenney with one of his pieces of art.

Rock ‘n’ Roll, caricatures, history and, oh, can’t forget the wine! On March 14, Montross native, Phil McKenney, shared his talent of combining history with music and art at Caret Cellars Winery. 

McKenney shared the history of mid-19th century Rock ‘n’ Roll in a unique fashion by not only his sharing caricature drawings of famous artists, but by also singing classics with a loud, full and in control voice that brought on nostalgia of the early rock era. His show, titled “Wild Men: The Dawn of Rock ‘n’ Roll,” has taken him all across the Northern Neck, Charlottesville, Southern Maryland, Richmond and Fredericksburg at venues such as wineries, women’s clubs, libraries and more.

With a tambourine at his side, McKenney sang Rock ‘n’ Roll classics such as “Shake, Rattle and Roll,” “Ain’t That a Shame” and “Tootie Frootie” while also sharing the history behind pioneering Rock ‘n’ Roll artists such as Alan Freed, Fats Domino, Wanda Jackson, Chuck Berry and more. McKenney’s crash course on the music genre was easy to follow and entertaining with its live performances and comedy. McKenney even shared the history behind Gene Vincent, a Rock ‘n’ Roll pioneer from Norfolk, Virginia.

McKenney’s inspiration to study the history of Rock ‘n’ Roll was actually an accident. He stated that one day he was looking for a good book to read, and ran across a book on Jerry Lee Lewis. He enjoyed learning about Lewis so much that he drew a caricature of him. From then on, he began creating his collection of artist caricatures. McKenney stated that after a while, it dawned on him to start telling the artists’ stories. 

So, how did this Northern Neck local decide to create one of the most unique history lessons to date? He simply stated: “I’m an illustrator by trade.”

At the age of 41, McKenney obtained his B.A. in Communication Arts, with a focus on illustration, at VCU. He stated that he first began drawing when he was old enough to hold a pencil. Throughout the jobs he worked, McKenney kept working at his artwork on the side until he decided to pursue his career in educating people while keeping them entertained. 

With a knack of singing, playing the tambourine and keeping a crowd laughing and singing, McKenney is a sure-fire entertainment talent that is creating joy and memories for all that have the pleasure of seeing his shows. In fact, he stated that his show at Caret Cellars Winery was his 175th performance. 

To witness the entertainment and talent of Phil McKenney, all are welcomed to his upcoming local shows at the Hague Winery Show on May 16 at 6 pm and the Montross Library for his “Teen Idols” show on May 18 at 6:30 pm. To book Phil McKenney at any venues, he can be contacted at


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