I first discovered Bolling's Little Archie stories when I was a kid in the late 70's and early 80's. Although he was no longer drawing the Little Archie feature at that time, his work from the late 50's and 1960's was being reprinted in the digests Archie Comics was publishing. At that time I had no idea what the name of any Archie artists was, outside of possibly Dan DeCarlo. I just knew which styles I was attracted to and the ones I gravitated towards. Bolling had stopped drawing the Little Archie feature in 1966 with the 38th issue, and Dexter Taylor took over the art chores completely. Taylor had pretty much been on the title since the beginning, sharing the book with Bolling and was still drawing the main title at the time I was reading them. Not to disparage Taylor's version but as a kid, I was drawn to Bolling's version that I was discovering through the digest reprints. As I grew older I discovered that the "good Little Archie artist" was Bob Bolling. I began a quest to track down the early LA comics, which was no small feat in the days before eBay. Through due diligence and so many wasted hours that could have been used for better and much more productive activities, I was able to piece together Bollings early run on the title from 1956 through 1966, as well as a few spin-off titles along the way. At that time (mid-1990's) there was very little information available about the history of Archie Comics, and almost nothing about Bob Bolling. Around the year 2000, I decided to write a letter to Bob Bolling care of Archie Comics in the hopes that it would reach him. I typed up a few questions and mailed the letter off (this is really dating me). I don't even remember if I knew if he was still alive, but I figured what the heck, it couldn't hurt. After a couple of months, I received a package in the mail from Bob Bolling himself! He was kind enough to answer all of my questions, and the best part was an enclosed drawing of Little Archie with Mad Doctor Doom and Chester! What a swell guy, eh? I've included the letter he sent me along with the drawing below. I didn't post the Q&A because, frankly, it's embarrassing. I believe there was an interview with Bolling in an issue of Comic Book Artist that came out a few years later that is much more informative. I recommend tracking that down for more information.
Below are examples of Bolling's work from the late 50's up to the mid-1960's. You can see his progression as a writer and as an artist. His early work had a more humorous bent whereas the later issues tended towards more adventure and fantasy fare. Both periods are great, but I tend to lean more towards the adventure stories.
Drawing by Bob Bolling, 2000
Letter from Bob Bolling, 2000
Inside Front Cover from Little Archie #2 1956
Little Ambrose #1 1958
Little Archie #12 1959
Little Archie #27 1963
Little Archie #29 1963