Perry Roskilly's source of inspiration for paintings of the naked bike ride is Annibale Carracci's fresco of the 'Triumph of Bacchus and Ariadne' (1597-1599). The energetic melee of naked figures in a Baroque composition drive relentlessly across the picture plain in a mutual acceptance of nudity, celebrated on a mythological plane of ecstasy.He looks at how Carracchi creates the skin tones and unifies the painting in time and space creating depth and proportion. This fresco is central to his thinking on the naked bike ride paintings, putting mythological figures into situations on the route of the naked bike ride on bicycles. He also draws inspiration from Michaelangelo, Rubens, Cezanne, Degas, Picasso and Caravaggio for a sense of how to paint flesh and treat anatomy.

After eight years of drawing striptease almost daily, Perry Roskilly came to find that in drawing movement, distortion happens as the girl moves and twists to the music. Even when taking a few seconds to make a sketch, by the time a breast is noted her legs may be circling to a new location as he tries to complete the sketch. When moving on to make a painting the line became fundamental and colour added to give sense to the line and character to the girl he was drawing.
The move to the naked bike ride enables him to explore the gamut of emotions experienced by participants of the ride, both together and in relation to bystanders clamouring to cheer, gawp and take photographs.