Holiday Silliness

Comedy is often found in the unexpected, a contrast between the serious and the frivolous, the modern and the old fashioned. Or, it may be discovered in the all-too-familiar. Such as here – the more accurate account of the holiday season. Specifically for those of us who don’t wrap presents like mall workers, have a Christmas photo with everyone smiling and can’t make it through the tree-decorating process without dad throwing out his back.


All Wrapped Up in Christmas—Richard Sargent

All Wrapped Up in Christmas
Richard Sargent
December 19, 1959

This dad is about to vanquished by his Christmas Eve wrapping project. Maybe he should have delegated this task to someone else…


Doggy Basket—Charles Kaiser

Doggy Basket
Charles Kaiser
December 19, 1942

Christmas, candy canes, and a puppy! There’s nothing not to love about this classic Post cover. Unless, of course you’re the dog who will be receiving a flee treatment and bath.


Santa’s Helper—Norman Rockwell

Santa’s Helper
Norman Rockwell
December 27, 1947

This retail worker is done with the holiday season and, by the looks of it, so is the store. Instead of working in the studio for this cover, Norman Rockwell setup shop in Chicago’s Marshall Field’s department store. The store happily provided the setting and toys for the scene but Rockwell felt the picture needed more dolls so he went out and purchased a large number of them. He joked with the Post editors that he owned more dolls than any other 53-year-old kid.


Hidden Gifts—Constantin Alajalov

Hidden Gifts
Constantin Alajalov
December 10, 1949

A cover revealing the difficulty even adults face when compelled to investigate their presents. Depicted by Russia-born artist Constantin Alajalov who specialized in illustrations gently pointing out human frailty. Though, it’s hard to fault this lady when the temptation lays less than five feet from her bed.


Trimming the Tree—George Hughes

Trimming the Tree
George Hughes

Can’t we all relate to the exhaustion after the Christmas decorating has ended? This man couldn’t even make it to a couch. In reality though, Hughes set the scene for this painting in June of 1949 after he ventured into the Vermont woods, chopped down a pine tree, took it home, and decked it with holiday cheer. He was forced to finish his work quickly, as the summer heat was causing the tree to drop needles and his 2-year-old daughter kept pulling off the ornaments.


Tree Love—Constantin Alajalov

Tree Love
Constantin Alajalov
December 23, 1950

As if one tree wasn’t difficult enough! Alajalov’s art can often be located at the intersection of cartoonish and realistic. His ability to combine a fashionable, clean stlye with warm-hearted satire was not only perfect for the Post but also for The New Yorker. He is the only artist to work for both magazines (each normally demanded exclusivity).


Christmas Photograph—Amos Sewell

Christmas Photograph
Amos Sewell
December 11, 1954

As the camera became ubiquitous, so did the family Christmas card. The only problem? Getting everyone to cooperate.


Topping the Tree—John Falter

Topping the Tree
John Falter
December 28, 1957

Tipping point? Falter specialized in capturing the comedy in family life, often delivering a small, humorous moral. We’d proposed, for this one, the lesson: “Behind every holiday-decorating hero is a woman firmly holding him upright.”


Christmas Morning—Ben Kimberly Prins

Christmas Morning
Ben Kimberly Prins
December 27, 1958

Prins artfully unveiled Christmas morning. This sweetly humorous illustration also has a wistful quality: All those weeks of preparation-the buying of gifts, the careful wrapping—then suddenly we’re left with a roomful of shredded paper.


Merry Christmas from the IRS—Ben Kimberly Prins

Merry Christmas from the IRS
Ben Kimberly Prins
December 17, 1960

How nice to be remembered with cards and packages bursting from one’s cheerfully decorated mailbox! But Christmas might be ending early for this man after receiving a notice from the U.S. Treasury Department.