The contest:
Using MSPaint, draw a picture of a pirate playing chess against a keg.

Most of the drawings are large. so if you’re using IE wait until the picture loads, then hold your mouse over the picture until the ‘expand’ button appears in the lower right. Click on that to view the picture in the proper resolution. OR, just view all the pictures in an expanded window.

We didn’t have quite the same participation as in the last few contests, but I suspect that this is because the topic was a little lackluster. I promise to put extra effort into the next contest topic!!

Entries (with brief commentary):

Please note the cost of the coffee items in the back. That’s right. Doubloons. Perfect.

Never has their been a better chess board drawn in MSPaint.

The sleeping pig? AWESOME. As is the fact that this pirate is a chick.

Czech Matey. heh heh. Very well drawn.

I really enjoy the ocean and scattering pieces. I keep finding myself looking at this one.

Interesting use of black and white. I like the Keg.

ha ha. there’s a K on the Keg. And the chess pieces are screaming for mercy.


Sweeping brush strokes! I enjoy the fluidness and real feeling of motion.

The little keg man in the lower right is hilarious.

Space pirate Ho! I love the borg cube and the chess board. Very fun.

I don’t think the artist was proud of this… but I think it’s good.

The face is really well done! I also really like the text. nicely done.


Vote by leaving a comment – no voting for your own drawing!

Also, the point tallying methods will be changing slightly.

42 thoughts on “PIRATES!

  • 10/14/2005 at 7:54 am

    1: 9
    2: 10
    3: Nothing. None of them were all that hilarious. I thought they were all great, but nothing tat made me laugh out loud. i mean there was like 7 uses of the joke “ARRRR!! Check Matey!” But great job everyone!


  • 10/14/2005 at 8:04 am

    Artistic – Pirate 9 is so nice to look at.

    Creative – Pirate 10 is possibly my favorite paint in the last three contests. It reminded me of the short story called “All the King’s Men” in Kurt Vonnegut’s Welcome to the Monkey House. I would be interested to know if the artist used this short story as an inspiration.

    Hilarious – Pirate 8 suprised me by using a non-traditional keg.

    I think MikeD’s is 12. Also, is pirate 3 a chick? I thought it was a guy with long hair. But maybe the artist just can’t draw faces well.

  • 10/14/2005 at 8:11 am

    1. 4, I really dig this pirate. Makes me think of Sid Meir games. Delicious.

    2. 10, because… well look at it, it’s awesome!

    3. 7, and only because the pirate has two peg legs. I imagine he was in a fight and one got taken off by a cannon ball. He probably thought “Damn, but I should expect that… I’m a pirate!” but when some jerk took his other one i bet he was depressed for a long time and drank a lot of ale, which is where he met this keg. In conclusion, God hates pirate #7.

    And a bonus award to #1 for being the first to reference PBR.

  • 10/14/2005 at 8:49 am

    1. #4 wins for best artistry; Varying thickness of strokes adds an element of realism and shadow that is nigh impossible to attain with the tools granted in the MSPaint palette.

    2. #10. Reminds me of the episode “The Rook’s Move” of “The Prisoner”. Also, the two commanders emerging from caves is classy.

    3. #1. The surreality of a PAINTING of a pirate battling a keg at chess… unbeatable. Also, thanks to the drink menu, you know the pirate lost his leg in a freak gasoline fight accident.

  • 10/14/2005 at 8:59 am

    Artistry: #10. There’s just so much to look at right down to the cannonballs on the ship!
    Creativy: #4 “Czech” I mean Come on.
    Hilarity: #7 THE PIECES ARE SCREAMING FOR HELP!!1!!shift1

    Mad Props to #9 for making me question my sobriety.

  • 10/14/2005 at 9:04 am

    I don’t know… 12 feels like the most miked like but “i be tapped” doesn’t sound like his humor.

    #5 looks like Jesse.

  • 10/14/2005 at 10:01 am

    I thought you would like it. I stole it from your site. I just didn’t know how to turn “Macgyver 2008” into the link itself. If you can go in and fix that, that would be grrreeeeaaaaaattttt……….

  • 10/14/2005 at 10:03 am

    I happen to think this drawing contest is better than the last and was not at all lackluster. I’ll vote later.

  • 10/14/2005 at 10:10 am

    1. MOST ARTISTIC: Pirate 4: good drawing, I am amazed at the artistic ability to make the pirate relaxed.
    2. MOST CREATIVE: I love Pirate 9. You’ve created your own art form in MSPaint.
    3. BEST MSPAINT HILARITY: Pirate 7: The fact that the pirate has two peg legs and two hooks shows how CRAZY he is. So crazy that he’s playing a keg in chess….

  • 10/14/2005 at 10:20 am

    Most Artistic: Pirate 9, really attractive
    Most Creative: Pirate 11’s pirate looks like the napster cat and the star trek theme is smart
    Best Mspaint Hilarity: Pirate 7, on top of everything everyones mentioned, the pirate also looks like indigo montoya.

  • 10/14/2005 at 10:37 am

    Hello, my name is Inigo Montoya. You killed my father, prepare to die.

  • 10/14/2005 at 10:41 am

    That guy is awesome in ‘dead like me’

    That’s all I have for now. I’ll vote later.

  • 10/14/2005 at 10:51 am

    1. 6 just looked cool
    2. 11 The star trek chess board was key
    3. 10 The little men made me laugh the most

  • 10/14/2005 at 10:52 am

    I met him in real life….he got fat, but was really nice

  • 10/14/2005 at 10:53 am

    It seems nerd references win this thing… Tim won almost completely on the strength of his Thundercats reference, now we got star trek vs. princess bride?

    I’m putting in as many nerdy references as i can fit next time.

  • 10/14/2005 at 11:25 am

    Artistry: #10, of course.
    Creativeness: #11….the pirate is the Napster dude, and Napster was PIRATING music…haha….
    Hilarity: #7. The keg’s expression is great.

  • 10/14/2005 at 11:26 am

    WHOA. Subtle pirate undertones. clever.

    was I the only one who didn’t pick up on that?

  • 10/14/2005 at 12:12 pm

    Patrick’s fly-by first impressions:

    1) I don’t “get” the Starbucks stuff, but then I live in Seattle. However, maybe there’s nothing to get, and it makes for a creative and memorable setting.

    2) This one leaves me asking questions like it’s an episode of Lost. What’s in that flowerbox? And who’s going to turn off the tap before drink spills onto the deck? What’s wrong with his eye? Is he going to stab someone?

    3) My favorite piece of this one are the three kegs of increasing strengths of X. I like the pirate treasure map. And the sleeping pig, like the Starbucks scene, makes it more memorable.

    4) Ok, this one begged me to look it up. Pilsner originally hails from Plzen, which is in Czech-land. I don’t know if having all of those other “check mateys” makes this funnier or not. Because it’s like, “this joke is overused, but yet it’s different!”

    5) Underrated feature of this picture: the stars! It gives the image a little more setting and depth.

    6) What is a knight fork? But then again, I’m not a pirate. I love the black and white (and subtle red!) on this one. So far, this is getting my vote for most artistic.

    7) I’m imagining the pirate with a French accent. I think it’s because of the curly moustache, hat, and hooks. Therefore, the keg shouldn’t be too worried: he’e french, and he has no natural limbs. Simple and cute.

    8) I recognize the pirate’s teeth from one of the clowns (or maybe a dinosaur), but I’m too lazy to go track down the artist. Also, how is this check mate? Assuming that black piece is a queen, the white king has two options. Ok, the ‘check matey’ is officially old, even the “ooh look at me at how witty I am” ‘czech matey’ variety.

    9) This reminds me of that optical illusion with the old lady and young lady, so I keep looking for the hidden hottie in the picture, but I can’t find her. This has got to be the most docile pirate I have ever seen.

    10) I like it. It’s thematically so different from the others. The shading is top notch. Thanks fo Mike D for pointing out the little keg man. I might not have noticed on my first viewing.

    11) I strongly considered having a music pirate for my entry, but then didn’t pull the trigger on it. (I thought I had something better, but after looking at the entries, I didn’t). However, I’m not a Trekkie, so I don’t think I can fully appreciate this one.

    12) That’s either the shortest pirate in history, or the largest chess table. I dig the floating eyes on the keg. It reminds me of some cartoon I saw as a kid, with floating eyes, but I can’t remember what it was.

    13) Wow, the last one, and very well done. The text is a little too fancy for my taste, but the reality of everything else is exquisite, especially the pirate’s face and sword. The pirate reminds me of that “happy trees” painter dude from PBS, only with inverted hair and attitude.

    My votes go to:
    Artistic: #13, in a squeaker with #6 (which would be in my top 3 overall, if not for the categorical format this time around)
    Creative: It’s gotta be #10
    Hilarity: #3, because it doesn’t use any overused pirate jargon, and it has 3 subtle humourous things: the treasure map, the pig, and the variety of keg offerings.

    Great work by all!

  • 10/14/2005 at 12:40 pm

    Artistic – # 9
    Creative – # 3
    Hilarity – #6

  • 10/14/2005 at 12:52 pm

    Artistic: 4
    Creative: 10
    Hilarity: 12 (The parrot’s drinking!)

    -Spelled “dubloons”, it’s not two of anything.
    -You know, in #8 it’s actually not checkmate.
    -In #10, zoom in on the pirates. The level of detail’s retardedly high. That little keg is halarious.
    -Please sir, I’m just a keg. Fantastic.

  • 10/14/2005 at 1:05 pm

    Not quite. My entry last week oozed of Star Wars, and I got one vote. So, go figure.

  • 10/14/2005 at 1:58 pm

    One, two, ready, play.

    Artistic: Pirate #13. (My guess is that this is Jesse’s). The beard and face are what won me over on this one. This pirate exemplifies “scurvy knave”.

    Creative: Pirate #3. The ambiguously gendered pirate, looking at the map, whilst a frosty brew or two sits on the bar and Hamilton the Sleepy Hog dreams of a house of bricks? No contest.

    Hilarity: I’m voting for #5 here. Why, you might ask? Well, it’s because of two things. First, the smile on the keg is classic – reminiscent of the Cheshire Cat. It’s the Cheshire Keg. Good stuff. Also, going with the Star Trek theme, doesn’t this pirate show a striking resemblence to Commander Riker? He’s got the beard, the dark red top, the black pants, the eyes, the hair…I bet he’s got Counselor Troi below deck in her “Sailing Wench” outfit.

  • 10/14/2005 at 2:25 pm

    Yeah, I thought the same thing about #8, Sander.

    #8 is not checkmate.

    And neither is #1. I can’t seem to find an combination of blue pieces in those positions that would force a checkmate.

    And neither is #2. It looks like all of the white pieces are pawns, so couldn’t the king move down and to the right? Perhaps my perspective is all wack, and the white pieces started at the bottom, and not the right. In that case, we’d have a stale, matey.

    And don’t get me started with #4. Not only isn’t it checkmate, but the pieces aren’t really on the squares! Maybe that’s how they play in Prague.

    The only one of the lot that has correct chess terminology is #6. Look at the knight. The keg’s got him.

  • 10/14/2005 at 2:50 pm

    Indigo Montoya…. Inigo’s long lost, severely disabled brother!!!

  • 10/14/2005 at 3:01 pm

    You both are obscenely fat though. So thats probably why you didn’t get it.

  • 10/14/2005 at 3:05 pm

    I have to say, I laughed more at these comments than for any other mspaint contest. I love how people noticed different things in each drawing.
    My votes go to:
    Artistic: Number 9. This one is awesome! I think my mom did this one.
    Creative: Number 6. The etching look and the creativity of design won me over. I think this one is Mike D’s.
    Hilarity: I would vote for my own, but I can’t, so I’m voting for pirate numero 11 because it’s quite funny in its interpretation of the drawing subject.

  • 10/14/2005 at 3:08 pm

    #2 is actually checkmate. The king can’t go anywhere without a pawn, is that what they are?, getting him. Well I guess you could say, its the pirates turn then he gots to move a ‘pawn’ therefore creating an opening for the keg to retaliate. But we’ll never know. Not until the artists are revealed! I can’t wait, the suspense is killing me!

  • 10/14/2005 at 3:51 pm

    I think the drinking parrot on #12 is really the key to the giant chess game they are playing.

  • 10/14/2005 at 4:41 pm

    Artistic: #4. I think it’s the only one in which the characters clearly have mood. The other ones imply mood, but this one just has it.

    Creative: #9 is so Picasso, or maybe Monet, or maybe some other artist, but those are the only ones in my artist vocab because I’m massively dumb, and that’s that.

    Hilarity: #6. “Why?” you ask… Look at how fat his face is and the complete lack of a neck. His head is garGANTUAN compared to his shoulders and his arms are so short. It screams Midget Pirate, which of course is the funniest thing I could possibly think of right now (total lie, by the way). If this pirate stepped into the light, he would certainly resemble a certain Daniel DeVito.

  • 10/14/2005 at 5:27 pm

    Kurt, I still don’t see the checkmate on #2, maybe it’s a perspective thing. Here’s how I see that corner of the board:

    Now, there are two ways to interpret this:
    1) The players started on the left and right.
    2) The players started on the top and bottom

    Assuming condition #1, it is not checkmate. The king can move diagonally one space. Since pawns can only attack diagonally forward, the king is safe there. Interestingly, under condition #1, with the pirate announcing checkmate, that would make you believe that he is playing white. But white started on the right side of the table, but the pirate is on the left.

    Assuming condition #2, the king cannot make a safe move. However, the king is set where he is, so therefore it’s a stalemate.

    Even if it’s white’s turn to move, white cannot force a checkmate with one move, in either condition.

    Now let’s examine another possible interpretation of the perspective, which is:

    Assuming condition #1 from before, the king could take the middle pawn and be ok.
    Assuming condition #2, the king could take the middle pawn and be ok.

    And, even after analyzing all that, there is still a disturbingly serious flaw with this match.

  • 10/14/2005 at 9:17 pm

    That pirate totally has a huge polygonal head. However I think that’s how pirates were. Think Marv from Sin City. With a hat. Kickass.

  • 10/15/2005 at 11:34 am

    These entries were all so good. This is going to be tough.

    1. Most Artistic: 4 – that pirate looks like Jesse (runners up: 3 – nice pig, 13 – an excellently executed drawing. I suspect Mike D did this one)
    2. Most Creative: 10 – the ridiculousness of this scene kills me (runners up: 9 – gestural expressionism, 6 – nice scroll thingy around the text!)
    3. 12 – what is going on in this picture? Is the pirate a midget? Is the pirate a 6 year old? Why is he so small? Why is that bird’s eye on the wrong side of its head? Why are there eyes floating in the middle of space? (runners up: 11 – what is that thing? I’m pretty sure it’s the little Napster guy, but I can’t be for sure. Are the keg’s hands magnetic? 2 – Nice feather.)

  • 10/16/2005 at 5:43 pm

    Actually, “doubloons” is correct and it is TWO of something. It has something to do with the coin being worth twice of some other value. So well done, Pirate 1. And Sander, IN YOUR FACE.

  • 10/16/2005 at 7:18 pm

    I was seriously blown away by all of the entries… there are some talented people on this site.

    MOST ARTISTIC: Pirate 4 – I like the perspective and the pirate’s posture, which is incredibly realistic.

    MOST CREATIVE: Pirate 10 – It’s a unique idea, the perspective is great and the little men are hilarious.

    BEST MSPAINT HILARITY: Pirate 3 – This one gave me the biggest chuckle. The map, the pig, the kegs with the increasing X’s… funny stuff.

  • 10/16/2005 at 10:36 pm

    I seem to remember seeing it spelled differently, perhaps it’s commonly spelled incorrectly? Either way, my mistake. Good catch, Jill Rogers.
    But where’s all this hostility coming from? Never come to the House of Rock while I’m here again, meanie.

  • 10/17/2005 at 6:30 am

    Actually, Jill’s last name “Rodgers” is spelled with a “d” between the g and the o. The D stands for Danger. And Jill can come to the House of Rock whenever she wants.


  • 10/17/2005 at 7:11 am

    Wow, Sander. I would say something about how I would totally kick your ass at the spelling bee, but I don’t want to extinguish that fragile flickering flame that is your ego.

  • 10/17/2005 at 7:53 am

    also, i’m fairly certain that Jill would win in a fight against sander.


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