Jackson — who is also a Grammy and Emmy award winner — is continuing to make history, specifically for Chautauqua Institution as he appeared for the first time on the amphitheater stage on Friday alongside award-winning poet and author Kwame Alexander.

Alexander welcomed Jackson to the stage with him, to help him close out a week of conversations and presentations about finding one’s passions, seizing opportunities and, ultimately, changing the world.

Alexander noted that he and Jackson first met in 2023 when Jackson hosted the Children and Family Emmy awards. The two began their conversation on Friday talking a bit about the creative process that Jackson has when it comes to music and songwriting, and the role music can play in people’s lives.

“I like to think that music plays a role of organizing the chaos of nature, the chaos of emotion, and in a singular way can focus it directly to the part of our hearts that needs to hear from it most,” Jackson said.

Christopher Jackson, most well-known for being the first man to take on the role of George Washington in the Broadway show “Hamilton” joined poet Kwame Alexander on the Chautauqua Amphitheater stage on Friday. P-J photo by Sara Holthouse

He said not all music that people listen to is everyone’s cup of tea, and specifically for theater the reason one goes to a theater is not necessarily the reason why they stay or they leave humming the songs afterwards. Music, he added, allows people to be reminded of their humanity and expand the capacity of themselves at any given moment.

Jackson and Alexander then discussed how Jackson once visited the White House during his time as George Washington, and performed in front of President Barack Obama in 2016. The pair briefly discussed how their ancestors as slaves would use music as a form of communication, and that music is more than just the song but also the action and choice to tell someone’s story.

“You’ve shown us that the reason we all come and gather here … is that ultimately we understand that we want to be together,” Alexander said.

Jackson told a bit about his story at the beginning of “Hamilton” and how he first found out about getting the role. At the time he was starring as Benny in “In The Heights” on Broadway, also written by Lin-Manuel Miranda, the writer and creator of “Hamilton”, and Jackson outlined how Miranda told him backstage about a new project he was working on “about the Treasury Secretary”, without many more details. It was a few days after that when his director of “In the Heights” referred to him as George Washington when Jackson first was told he was going to play the role, and which Jackson said at the time he had no idea what his director was talking about.

Jackson talked about reading the biography of Washington seven times to prepare for the role and some of the similarities he felt with the man and character, such as having a life defined through loss. Jackson said Washington lost many people important to him at a young age, and Jackson himself lost his father — who he had a strained relationship with — during the first week of previews during the opening of “Hamilton”.

Christopher Jackson and Kwame Alexander talk with two kids during their lecture at Chautauqua Institution.

Alexander then talked about a sermon he attended at Chautauqua earlier in the week about the power of choices, asking Jackson about how his choices have shaped his life and got him onto his path. Jackson said a lot of his choices boiled down to the choice to say yes to things, being willing to be uncomfortable in front of a crowd of people, and that all of his successes he did not accomplish on his own, as they were all with others in a show or on stage or as a collaboration or influenced by others in some way.

Alexander has been at Chautauqua throughout the week, talking with different people throughout as a part of this past week’s lecture series, all with the theme “The Power of One”. He said the idea of Jackson’s success being influenced and brought on by collaborating with others ties right into that.

“What you’re suggesting is that the power of one is really us,” Alexander said. “The power of one is being able to recognize that we are one; so the one is not singular, but perhaps it is community.”

Alexander then welcomed two kids onto the stage to talk with him and Jackson for a bit, including one who came dressed as Washington and rapped a little bit of the “Hamilton” song, “Are You Aaron Burr, Sir?” Following some conversation and questions with the kids, who Alexander had met earlier in the week, he said he brought them on stage to emphasize the point that everything people do is to ensure that who they love and leave behind have better lives and opportunities than themselves.

Jackson then talked a bit more about his past, specifically places and family in Illinois, and the “bubble of love” he grew up in. Alexander asked what Jackson considered his most powerful moment on stage to be, and Jackson said it is whenever he is able to make an audience laugh.

“Knowing that either by a look or note or movement I’ve been a vessel of expression,” Jackson said. “The reason why we all gather together is to feel and hear something we already know about, so it reaffirms something, or that we disagree with so we’re here to possibly be convinced of a different thought, or that we’re here to give expression and release to thoughts and feelings and ideas that are not easily expressed, because why? Because we’re human beings and that’s really hard to do and somehow by standing on a stage and amplifying our voices we make it look a little less daunting.”

To wrap up the day, Alexander talked about how he and Jackson are working together on a collaboration to create a musical of Alexander’s book “The Crossover”, with Jackson composing the music and which will be produced by the Chautauqua Theater Company, their first musical commission. Alexander, who has had everyone he talked with throughout the week respond to a piece of artwork, then read a community poem alongside a professional violinist, and had Jackson respond to it with a song of his choice. Jackson chose to sing “Lovely Day” by Bill Withers.

The overall event ended with a short question and answer session, followed by a meet and greet on the back porch of the Amphitheater.