Lackadaisy Flimflam

No.  I didn’t reference any faces for the artwork, and definitely didn’t want him to look like any specific person, celebrity or otherwise.  I’ve received messages telling me he looks like Chris Pine, Zac Efron, Emile Hirsch, Robert Sheehan, Robert Pattinson, young Val Kilmer, Alexander Rybak, Justin Bieber, Peter Pan, Dmitri from Anastasia, Tom Sawyer, several “a guy I know”s, and some I’m forgetting, though.  I can’t fathom in what way he resembles some of those but, eyebrows aside, he does have a sort of generi-face.  I can understand how that might register as any number of young men to an onlooker.  Oh well..

What are the reasons a barefoot hellion child wouldn’t have a brick on a rope?

Sometimes it happens immediately, sometimes it requires pages and pages of awkward drawings and conceptualizing and writing before their personality and design seem to move into alignment where everything sort of clicks.  Once that happens, though, it begins to feel more natural to draw them, and to do so in ways that reflect who they are.  (Rocky’s face is built around the arches of his brows and smile, tapering off into little devil horn points.  Freckle has the repeating round shapes of guileless youth, cue ball head and saucer eyes.  Zib’s, sleek, but with a lot of prickly anxiety underneath, is all acute angles and narrow triangles.)
They never really seem to stop ‘evolving’ though - a not altogether unwanted side effect of time, I suppose.

No…but he does have a cactus friend.

I use the mid to late 20’s, generally.  It’s a fashion era that’s pretty easy to distinguish from the early 20’s and early 30’s.
The early 20’s maintained a lot of Belle Epoque / Art Nouveau sensibilities - softer looking in form and employing a lot of gauzy layering and lush, organic patterns (top image).
The latter half of the 20’s was distinctly modern and almost assertive looking by contrast, where Art Deco had become the prevalent mode. (middle image)
In the early 30’s, the overall shape of clothing underwent more noticeable changes.  It was a conservative time compared to the hedonistic 20’s.  Dresses got a bit longer and waistlines returned to their usual location as the more traditional female shape became fashionable again. (bottom image)