While the Invitational is primarily a “word person’s” game, it’s the maniacal cartoons by the semi-maniacal freelancer Bob Staake that establish its zaniness to the unwary.

Bob started illustrating the Invite’s weekly contest in 1994, and he has drawn close to 1,000, not to mention dozens of Invite caption contests. In the meantime, this weekly taint on his résumé has inexplicably failed to keep Bob from picking up pocket change and a house/studio on the Cape Cod waterfront as the writer and/or illustrator of more than 50 children’s books, among them the bestsellers “The Donut Chef,” “Look! A Book!” and “The Red Lemon,” and regular appearances slumming on the cover of the New Yorker. His favorite Invite cartoons are sprinkled through these pages.

But the Loser Community itself is also responsible for some of the Invitational’s most memorable pictures. Perhaps the most striking came to us when Fred Dawson of Beltsville took the Empress aside at the 2005 Loser holiday party and whispered: “Would you like to see a really bad painting? I did it myself.” For a long time after that, if you Googled “world’s ugliest painting,” you would see the portraitof Red-Haired, White-Faced, Joker-Mouthed, Drumstick-Armed Girl that Fred donated as a prize.

The winner regifted the Ugly Painting, then won it right back in a contest for what to do with the thing. It eventually went to someone who’d painted a mirror image. The Ugly Painting became an icon for the Loser community, featured on the Losers’ name tags at Loser brunches. And Loser Stephen Dudzik even made them into genuine U.S. postage stamps through Zazzle.com.

And then are the several contests in which we asked for art by the Losers themselves — in 2006 and 2011, photos featuring food (Jeff Brechlin’s “Dorian Grape,” from Week 657, 2006, is pictured here); in 2007, fun with household gadgets; and in 2008, illustrating any of five captions we supplied first.

Be sure to check out the many other segments of this 20th-anniversary Style Invitational retrospective: classic limericks; song parodies; neologisms (new words); horse “breeding” and “joint legislation”; and dozens of other winning entries from the past decade. Plus how to enter this week’s new contest, and a look at the Losers and their remarkable subculture. And more! See the index of articles here.

We left out your favorite entry? Let the Empress know at The Style Conversational.