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The Largest On-Line Stash of Robert Osborn’s “Dilbert”

Robert Osborn

I’m not much for compiling lists of favorites, but if I had to ever list my favorite cartoonists, there’s no question that Robert Osborn would appear high atop the pantheon of greats alongside other cartooning heroes like Ronald Searle, Otto Dix, Vip Partch, Rowland Emett, and Miguel Covarrubias.

Osborn’s work has been on my mind recently. His name came up in a conversation a few days ago, and then there was Jerry’s post about Grampaw Pettibone, a character that Osborn designed and drew for a long time.

Robert Osborn

Osborn is the definition of late bloomer. He was approaching forty years old when he began drawing cartoons for the Navy, his first major body of work. He created between 2,000-3,000 drawings for posters and military training booklets, many of them featuring Dilbert, a goofball pilot who did everything incorrectly. It’s a crime that these drawings have not been collected nor reprinted anywhere since their original publication seventy years ago.

Thankfully, there’s the Ask a Flight Instructor website, an unlikely repository of Osborn’s work, collecting nearly 600 of his drawings from that era. It’s easily the largest collection of Osborn’s wartime work that I’ve ever seen and it’s a real treasure. The drawings are all related to the operation of aircraft and aimed squarely at pilots, but from a cartooning standpoint, they can be appreciated by all.

Robert Osborn

The first thing that strikes me about these drawings is the quality of Osborn’s line. The texture, the dynamism, the intensity–diminished somewhat by the low-res scans on-line, but still plainly evident. In my opinion, he had the most exciting line of any cartoonist.

Years ago, I had a conversation with cartoonist Eddie Fitzgerald and he theorized (quite eloquently, I might add) that the content of Osborn’s work was overshadowed by the sublime beauty of his line. I wouldn’t go quite that far, but the point is well taken–Osborn’s line is that of a master draftsman’s; we’d be more accustomed to seeing such elegant work hanging in an art museum than reprinted in instructional booklets for aviators. Osborn, said art historian Russell Lynes, “has never been one to observe too closely the distinction between cartooning and pure painting.”

The real thrill, however, is seeing how Osborn applies that line to the art of cartooning. He doesn’t hesitate to twist and distort forms, caricature expressions, anthropomorphize airplanes, and gag up an idea. And he does it all using a naturally funny and inventive drawing style which evolved to even greater heights in the years following his Navy cartoons.

Robert Osborn
  • Reminds me somewhat of Graham Annable (Grickle’s) work, whose work and penmanship and angular forms and shapes I also admire. I’m oretty sure I won’t be the only one to make that connection. Love the eye on the left plane in the ‘taxi dermist’ picture. Could have been done by Joan Miró, but maybe taking things a little far.

  • Uli Meyer

    Otto Dix? A Cartoonist? Hmm…
    Thanks for the link to Osborne’s work! How refreshing to see such honest drawing! Not a vector line in sight. Hooray!!!

    • amid

      Uli – I consider cartooning to be a subset of art in general. To be a great cartoonist, one has to be a great artist too. So while Dix was certainly other things besides a cartoonist, when I see his work, I see someone who applied the principles of cartooning better than almost anybody else. That’s why I consider him a personal favorite, though I understand not everyone wants to attach that label onto him.

      Otto Dix

      • Uli Meyer

        Depends on how you define cartooning. Over here the word cartoons is usually used for news paper strips and gag drawings whilst the work of Dix and Grosz would be described as satirical art. When I spoke to Ronald Searle I always felt that when you talk about his work as “cartoons”, it doesn’t sit that easy with him. In the “fine arts” world, if you were to label Dix a cartoonist, you’d be beaten up with Tracy Emin’s bed posts.
        As a cartoonist myself I think that is all nonsense and am happy to be in such marvellous company.

  • Paul D

    Love these!

  • eeteed

    is eddie fitzgerald related to owen fitzgerald?

    • I asked him. He said no.

      Anyway, I will say that this is much better drawn than that other, more famous cartoon named “Dilbert”.

      • eeteed

        much thanks for the info, charles!

  • Wow! I wish I could capture that energy in the strokes Osborn does. Also, it’s really inspiring that someone who started as late as he did was able to produce such amazing work.

  • tedzey

    now THIS is the look I wish to get from my comic strips! Great post, this website is always a treat to visit!

  • Steven M.

    Such beautiful works of art. I’m in love.

  • Wow thanks for this. Have been a big fan of Osborn since my early twenties–he is unfortunately too little known today. I rank him right up there with James Thurber… Too bad nobody ever seriously tried to capture his style in animation… (IMO the “Grampaw” shorts posted yesterday from both studios simply ignored his designs in favor of predictable generic treatments, unfortunately…)

    Great to have this stash to pour over-pure inspirational gold… Thanks again.

    • amid

      Will – I think Bill Littlejohn was perhaps the most sensitive when it came to respecting Osborn’s original designs in animated form: http://bit.ly/igEwz9

  • Good call Amid. I remember that spot now–it was a real attention getter and still holds up beautifully…

  • Kevin Martinez

    Wasn’t the Scott Adams Dilbert named for this Dilbert? I distinctly remember Scott Adams talking about, in one of the retrospective books, how the name was introduced to him by a co-worker who got it from an older WWII-era comic.

  • Paul M

    I’d never heard of Robert Osborn – I love anything to do with WWII aircraft, my dad had an old book of RAF cartoons from the period that were very similar. Thanks for sharing.

    When it comes to cartoonists with a perfect line, however, my favorite will always be Al Wiseman. The best place to find his work is at Pappy’s website:


  • Great stuff! Reminds me of Harvey Kurtzman a little.

  • Great stuff. Love Osborn. They had a book of his stuff in the Calarts library when I was there. I know Teddy Newton was also a fan. You can see Osborn’s influence in his work.

  • Ted Wilbur took over the Grandpaw Pettibone cartoons in the Naval Aviation News magazine- I kept some of them just for the ‘toons, which are quite brilliant as well.

  • I actually own an anti-war book by Osborn. It is called War Is No Damn Good… the thing I find completely fascinating is that it was published in 46. So around the same time he is light-heartily poking fun at the Navy he has strong opinions about any military practice. Of course the drawings are amazing…less comic strip and abstract pieces. His contrast is enviable.

  • My grandparents had a book of “science riddles” illustrated by Osborn and I loved the cartooning in that book. Simple, simple drawings that were amazingly effective. I used to copy some of the cartoons and try to make his big-eyed, noseless thinkers. (I still do.)

    Years later, during my undergrad, one of my art professors brought in a pile of books illustrated by Osborn, most of them little hardcovers about the foibles of life. I eventually found one of those at a 2nd-hand book store and snagged it. I should revisit it tonight and see if I can get a copy of the science riddles book, too.

  • This art style reminds me of Graham Annable. It must be the big noses and expressions.

  • Jason Novak

    You can also find many of Osborn’s illustrations by looking through issues of LIFE magazine in Google books, including a couple great covers. Though a late-bloomer in cartooning, Osborn was a classically trained fine artist and instructor for many years beforehand, which probably accounts for the subtlety, expressiveness, and confidence of his marks. He also worked almost exclusively in dry media – common enough then, but quite rare now. Amid, I’d be interested in your thoughts on why so many cartoonists have abandoned charcoal and graphite.

  • SKronquist

    I have a large collection of WWII US Navy Osborn prints that I am interested in selling. In fact, I have almost a complete set of the 385-770 series (I’m only missing about 10 of the prints), as well as some of the 800 series prints. Does anyone know what they are worth and how I should go about selling them? Thanks!

    • Jason McKeon

      SKronquist I would like to talk to you about your posters. The Dilbert posters on Ask A Flight Instructor are from my collection. I now have about 900 Dilbert and about 150 Spoiler the Mechanic.