The Big Yin completed the six drawings as part of his Born On a Rainy Day series.
In a video filmed at his home in the Florida Keys, Billy, who has Parkinson’s disease, looked healthy as he spoke about creating the works.
The drawings include one called Wearing The Ring, which shows a figure trying to lift a ring-shaped weight.
Billy, 78, said: “Wearing The Ring is a shallow look at gymnasiums. I hate them. I have tried all my adult life to be the same shape as those guys who work there but I can’t, I’ve given up. The ring is a nod to a piece of equipment.
“It’s about the torture I have undergone in gymnasiums.”
Another drawing is of a multicoloured baby holding two tambourines and is called Tambourine Man in tribute to the Dylan song. Billy said he loved Dylan and described him as his “hero”.
The comic, who retired from stand-up in 2018, told how he was now using more colour in his drawings but wanted them to retain their “melancholy”.
The drawings will go on sale on March 7 through Castle Fine Art.