It would be impossible to overstate the admiration I felt for comedian Stephen Colbert in my early 20s. As America stumbled into successive disasters during the George W. Bush presidency, Colbert’s pitch-perfect parody of a hyperpatriotic news anchor on Comedy Central exposed the self-important stooges who operated the machinations of government and media. And it was funny as hell, from the eagle’s cry at the beginning of the intro to the rippling American flag graphics to Colbert’s pretentious lift of the brow.

At the 2006 White House Correspondents’ Association dinner, Colbert crossed over from comedy star to folk legend. In one of the most daring moments in the history of American comedy, Colbert delivered a searing and uproariously funny roast of the most powerful man in the world, sitting only a few feet away. As the 17-minute bit ran its course, Bush’s good-natured grin morphed into a spiteful grimace. It later emerged that his team hadn’t properly vetted Colbert’s act and thought he was a conservative comedian (heckuva job, everyone!). Colbert went for the jugular. It remains one of the most quintessentially American cultural moments: no royalty, no ceremony, no limits.