No president wants to be known as a big joke - except on the night of the White House Correspondents' Association Dinner.
Each spring, the commander-in-chief sets aside his usual gravitas to tickle the funny bones of the White House press corps - and their celebrity guests.
The Correspondents' Dinner - or "Nerd Prom" as it's affectionately called in Washington - is a delicate balancing act: Jokes should be "edgy enough to get a laugh, but not dangerous enough to get you into trouble," according to former Bill Clinton speechwriter Jeff Shesol.
President Obama is no stranger to satire. He tested his comedy chops earlier this year on Zach Galifianakis' "Between Two Ferns." And he's already taken the stage at the dinner five times before. From cracks about the first daughters' potential beaus to jabs at his political opposition's personal grooming habits, here's our roundup of the president's best WHCD jokes to-date.