Deciding that Bolling was better at drawing children than adults or teenagers, Archie editor Harry Shorten assigned him to work on Pat the Brat, a comic about a child with an obvious resemblance to Dennis the Menace.

When the designs were approved by Goldwater and Shorten, Bolling was assigned to write and draw the first issue of Little Archie.

From 1957 to 1965, Bolling worked exclusively on Little Archie, writing, drawing, inking and lettering approximately half the stories in each giant-sized quarterly issue.

The character made his debut at "approximately the same time" as Marvel Comics' Victor Von Doom.

In between Archie assignments, Bolling wrote and drew the first two issues of Marvel Comics' Wally the Wizard.

"[6] Jaime Hernandez has said that Bolling's influence "is the reason I write the way I write,"[8] adding that he is influenced by Bolling's controlled sentimentality – "he knows when to back off; he knows exactly what to put in and what to take out, and when" – and by his ability to convey moods and times of day in his stories: "As a kid, I could just feel myself outside when I was reading them – being by myself when the stillness of the afternoon is spookier than the dark of the night, you know?

[9] He was presented with the Bill Finger Award for Excellence in Comic Book Writing at San Diego Comic-Con in 2022.