It's a Hollywood-Washington mash-up that always teeters on becoming a smash-up.
Conan O'Brien brought the late-night comedic chops as host of the White House Correspondents Dinner on Saturday night in Washington D.C.
But it was President Obama who got in the best zingers – much to the delight of the famous faces in the crowd.
"I just witnessed our President deliver the funniest speech I have ever heard," Tweeted Katy Perry
Then O'Brien had his chance.
"Right now - Conan. Is killing it!!!" added Julia Louis-Dreyfus on Twitter.
It was definitely a star-studded night.
Look among the tables of politicos for the likes of Sofia Vergara
, Rebel Wilson, Connie Britton, Amy Poehler, Jessica Pare, Julie Bowen, Kerry Washington and Hayden Panettiere.