Worst Painting Ever, Dave Santillanes

I was painting alongside a road in Wisconsin recently for the Door County Plein Air Festival and, while focused intently on finishing up what would certainly be seen as a masterpiece someday, I was interrupted by a young art critic who yelled out “WORST...PAINTING...EVER!” as he drove past.  Now, this painting didn’t end up being the masterpiece I expected, but I was convinced that it showed enough skill to avoid being the WORST.  And honestly, if this guy had seen some of my earlier outdoor paintings he might not have spoken with such conviction.   But all of this got me thinking - what defines our best and worst efforts outdoors?  If the goal of a plein air painting is a finished masterpiece, judging the result is more straightforward.  But if the goal is simply to “study” - to learn and gather information in order to develop a finished masterpiece in the studio - which is what my aim is,  it’s a little more difficult to quantify the results.  Especially if you’re like me and learn quite a bit from making mistakes.  If this is the case it might just be entirely possible to paint the “Worst Painting Ever” and also have it be the “Best STUDY Ever”.


Norman Rockwell , “Girl Running with Wet Canvas”. \  All is not lost when you have to quit because of a thunderstorm.

Norman Rockwell , “Girl Running with Wet Canvas”. \

All is not lost when you have to quit because of a thunderstorm.

Since the time I began painting outdoors some 16 years ago, my goal has always been simply to STUDY.  To figure out exactly how nature works and translate what I’m seeing into paint.  So although I joke that my aim is to paint the “Best Painting Ever painted”,  I’m hardly ever looking for a finished piece outdoors.  Instead, I want to capture only the things that I can’t do in the studio - things I can’t get from a photo.   I’m taking notes on color, light and atmosphere.  And my focus is usually on the shadow shapes where I want to establish their exact value, color and temperature.  I’m arranging those shapes to lay the groundwork for overall design but I’m not obsessing about composition at this stage - there’s plenty of time for that in the studio.   In fact sometimes when I’m in the field, I’ll often ignore composition all together, especially when time doesn’t allow it... like when an afternoon thunderstorm moves in and I’m about to get struck by lighting.  This might make for a bad painting but not necessarily a bad study and definitely a smart one. 

Once I get back to the studio where time is more abundant, I’ll take those brief, pre-lightning notes and spend hours, maybe even days working out composition. For me, creating a painting on the spot with the same refinement as a studio piece has never been part of the plan. But, what I’ve found is that within these brief - sometimes hurried notes - occasionally a finished painting emerges all on its own.  In fact, a mere study, in it’s brevity can indeed be beautiful - even beyond the beauty of a more refined piece.  As Charles Hawthorne, founder of the Cape Cod School of Art once said, “A sketch has charm because of its truth – not because it is unfinished” .  I describe it as “poetry” to a “novel”... or an encyclopedia as the case may sometimes be.  And although it’s no use arguing this case with someone at a plein air opening who doesn’t understand why every speck of the canvas isn’t covered in paint, there are plenty of examples throughout history of studies that qualify as masterpieces.  But this doesn’t always happen and sometimes a study is just a study.  It may even be the worst painting ever.

“A sketch has charm because of its truth – not because it is unfinished” – Charles Hawthorne

Dave A. Santillanes “The Storm Begins”, oil, 12x9 inches

This was a 1.5 hour study that I tried in vane to paint larger in the studio.  But to no avail. Although the larger painting had more “words” it said much less.

Bato Dugarzhapov “Winter Sunset”, oil, 12x14 inches

I have no idea if this was an outdoor study or an indoor masterpiece but it doesn't matter. It's beautiful in any regard and says all that needs to be said with only a few "words".

John Singer Sargent Mountain Fire (Watercolor on paper. c1903. Brooklyn Museum of Art.)

In this brief study Sargent is focused only capturing that brief light of alpine glow.  The foreground dissolves into obscurity since it isn’t the focus of this painting.  What more needs to be said in the studio?



Whenever a painting fails miserably outdoors for me (or indoors) I euphemistically call it a “nice study”. If you happen to end up with one of these all is not lost.  After all you’ve just spent two hours intently observing the scene... you’re now the visual expert of it.  If anyone asks you a question about this place and the two hours you spent there, you have the answer.  Once when I was painting near my home, four police cars pulled up and one of the officers jumped from his car, approached my setup and, catching his breath asks, “have you seen a short, Hispanic male with a baseball cap running through the area?”  My first thought was that I fit this description precisely, but, realizing I wasn’t their suspect I was honored that they had come to me for my visual expertise on the scene.  I considered offering my painting as evidence but instead just answered “No”.  The point is don’t discount an intense 2-hour visual study of a scene. Many things will happen in those two hours to create the “story” that you want to tell.  And be confident that you picked up a thing or two regardless of how the painting turned out. For me, once a painting falls short of my lofty visual goals, I don’t try to whip it into shape in the studio by painting over the top of it and destroying my notes (good notes or bad).  And I don’t go back to the scene multiple times with the same canvas.  If I return to the scene it’ll be a new attempt, a new story with a new canvas.  But what I do instead is use my plein air notes and photos in the studio and seek out the good stuff.  I’ll analyze the notes I got right and try to make sense of the notes that are too vague.  I’ve learned that even my worst efforts outdoors contain something useful to help read and interpret photos from the scene.  There are just too many good, often unintentional, things that happen when we paint outdoors.  In our haste to capture a fleeting moment or escape a coming storm, we subsequently distill the scene down to only the essential elements - elements that tell the exact story we want to tell - without all the peripheral distractions.   In working fast and simplifying we don’t have time to paint the things we don’t want to or aren’t interested in painting - and that’s a good thing.  

John Singer Sargent Studies for Madame X portrait.  1883. Graphite and Watercolor. These quick sketches might not pass for masterpieces.  But the resultant studio painting certainly does.

John Singer Sargent Portrait of Madame X.  1883. 93x44 inches, Oil on Canvas


Robert A. Thom The Mighty Babe (Oil on Canvas. 1976. Baseball Hall of Fame, Cooperstown, NY.) Babe Ruth pointed to the stands and then knocked one out of the park.  But in painting sometimes a swinging bunt with a few errors in the field will also get the job done.


Ultimately what I’m saying is RELAX and remember how much fun this is.  I teach several workshops throughout the year and I’m always imploring my students to leave their frames at home when we go out painting for the first time.  I’m not trying to lower the bar for expectations but simply reminding them that painting outdoors is only one part of the process.  The goal is, of course, to take GOOD notes as opposed to BAD ones, but it’s my way of saying don’t put too much pressure on yourself because there’s something to learn from the bad ones too.  So my advice to every plein air painter is to get outside, “point to the stands” (as my friend Joshua Been is fond of saying), and paint the worst painting ever, it might just be the most valuable study you’ve ever done.






Dave Santillanes Worst Painting Ever, Oil, 12x16



Yep, here it is.... the worst painting ever!  Stay tuned, this may just end up a masterpiece someday.






Visit Dave's website to see more of his work.

Lori Putnam29 Comments