In 2009, comedian Jon Stewart mocked President Obama on “The Daily Show” for hosting an evening poetry jam at The White House. Near the end of his rant, he specifically ragged on one of the artists, a Broadway singer, for his performance as Vice President Aaron Burr singing about Alexander Hamilton.
“You’re rapping about Alexander Hamilton?!?” said Stewart. “This is kind of ridiculous. A black man in the White House, so you can stop now.”
That song would go on to be the opening number for “Hamilton” the musical, which earned a record-setting 16 Tony nominations, winning 11, including Best Musical, and was also the recipient of the 2016 Grammy Award for Best Musical Theater Album and the 2016 Pulitzer Prize for Drama.
The man performing at the White House in 2009 was, of course, now-celebrity Lin-Manuel Miranda. Michelle Obama would later say that “Hamilton” is the best work of art she had seen in her life.
“I’m actually working on a hip-hop album,” Miranda said that evening. “It’s a concept album about the life of someone I think embodies hip-hop: Treasury Secretary Alexander Hamilton.”
It must have been even more awkward for Stewart when President Obama appeared on “The Daily Show” in 2015, just after seeing a preview matinee of the musical. According to Broadway Black, Obama told Stewart backstage that the show was “Phenomenal!” and “went on to remind Stewart that Lin-Manuel Miranda performed what would be the opening number of the piece five years ago at the White House.”
Thankfully, Stewart wasn’t the one green-lighting the now culturally-mainstream performance, and the show survived his harsh critiques. In the end, it was Stewart’s sassy segment that did not age well. Mocking a nerdy, history-focused rap at the White House was low hanging fruit coming out of his writers’ room, and Stewart probably regrets running with it.