New Year’s Eve has always been a moment of permission: to drink too much, flirt too freely, and make promises that feel sincere in the moment, even if they’re destined to unravel by morning. In the pages of Playboy, that moment was often captured through cartoons – sharp, indulgent, perfectly timed to land somewhere between aspiration and aftermath.

Across decades, these New Year’s cartoons did more than chase a laugh. They appeared alongside essays on literature, politics, culture, and power, creating deliberate tension between seriousness and satire. An office cocktail party gag appears next to an essay about the next great literary classic. An unexpected “Happy New Year” shares space with reflections on civil unrest. In later years, mafia axioms shared the page with New Year indulgence. 

Through champagne flutes, party debris, and as few clothes as possible, Playboy cartoonists captured what New Year’s Eve has always been at its core: the hopeful reset we half believe in. 

John Dempsey frequently upended corporate culture in his cartoons – putting buttoned up office life in scenes of unmistakable Playboy excess.

Alden Erikson’s cartoons were a staple of Playboy in the 1960s, 70s, and 80s, his humor often landing in unexpected places. Another Erikson cartoon welcomed 1966 with an immediate resolution—one we hope is also on your list.

Indulgence is no longer just expected – it’s upgradable. Why simply “blow” out the old year when you can start the new one with a bang? 

Robert “Buck” Brown was best known for his highly sexed, toothless, “granny” character, but this New Year’s Eve, he traded caricature for chaos. What we’re left with is not the party itself, but the wreckage: bodies slumping, unexpected characters all around, and an audience enraptured with the spectacle. 

Happy New Year’s Day. John Dempsey captures the divide between excess and the optimism of resolutions.