Onstage in Broadway’s Hamilton, Chris Jackson is the only person who gets to boss Lin-Manuel Miranda around—his towering George Washington refers to Miranda’s Hamilton as “son” and gives orders that, even when Hamilton doesn’t like it, he abides. But backstage, the creator and star of the Pulitzer Prize-winning Hamilton is the one in charge, right?

Well, actually, “I'm still probably the only person who can fuss with Lin and he'll listen,” Jackson says. “But he doesn't listen that well.”

Jackson goes further back with Hamilton than nearly anyone other than Miranda himself; he first met the writer and star, along with director Tommy Kail, in 2002, when Miranda and Kail were fresh out of Wesleyan and in the nascent stages of developing the musical In the Heights. Jackson originated the role of Benny, the show’s only non-Spanish-speaking character—like Washington, a character who stands apart from the rest of the cast. When Miranda presented selections from what was then The Hamilton Mixtape, in 2012 Jackson was there as Washington, and has played the role in every iteration since.

Miranda has described both Hamilton’s version of Washington and Jackson himself as a combination of Common and John Legend, a comparison Jackson modestly brushes off. But he admits he was at least an older brother figure long before he became a Founding Father.

“I was very protective of Lin,” Jackson recalls from the early days of In the Heights. “I very much took on a big-brother role with them and still do.”

Jackson was a Broadway veteran by the standards of the youthful In the Heights cast, having snagged a role in 1997’s original Broadway production of The Lion King “an hour before the first rehearsal.” The job came so last-minute, in fact, that he kept working his restaurant job for two more weeks “just so I wouldn't leave [my boss] hanging.”

The Lion King also prepared Jackson for the blitz of attention that comes with a Broadway hit—The Lion King won six Tonys and is the third-longest-running musical in Broadway history, a fate that Hamilton seems easily to match. But now in his 40s with two kids at home, and performing each night alongside close friends, he says, “Hamilton doesn’t compare to anything I’ve ever done. With the exception of In The Heights I've never been as emotionally invested in anything that I've done, and I've been invested in everything that I've been a part of, but this requires so much more. It's my best friends that have written this thing and included me in it. So it's a different kind of experience.”

The whirlwind of Hamilton has led to plenty of surreal moments for Jackson and his castmates, from multiple visits from President Obama (“When he comes in and gives you a pound and a bro hug, I mean, I'm not going to say no”) to a successful campaign to keep Hamilton on the $10 bill. But for Jackson, a West Wing superfan and subscriber to The Washington Post’s Presidential Podcast, the trip to the White House may linger longest. “We did a Ham4Ham parody, where we did the first Cabinet battle in one of the parlors downstairs, and it was crazy. It's just a little corner office, but it's just knowing that we're there. My mind is blown.” (Talking about encounters with famous Hamilton fans, Jackson sounds nearly as starstruck by The West Wing star Bradley Whitford as Obama, and calls the Aaron Sorkin show the “shorthand“ between him, Miranda, and Kail).

Though he’s careful not to indulge in “Founding Father chic,” Jackson has a clear reverence for, if not the people depicted in the show, the history they represent. “That brick that you're standing on, that foundation that you're standing on, there's a brick in there that was placed by someone you never knew, sort of a faceless possibility, but you're there now. You have an opportunity to put your own brick in there. That's what it feels like we're doing with Hamilton.”

The show, as the millions of people who have obsessively listened to the soundtrack know, is consumed by the idea of legacy, and in the final song the cast faces the audience and asks repeatedly “Who tells your story?” It’s in that moment that Jackson and director Kail came up with a way for Washington—and Jackson himself—to acknowledge his role in perpetuating slavery, an issue addressed only on the fringes of the musical. “It's something I spent a lot of time and a lot of angst trying to figure out how I reconcile being in this man's skin,” Jackson says. “As a black man, I just couldn't put it together.”

In the song, which is mostly about Eliza Hamilton’s life after her husband’s death in the famous duel, she sings about raising funds for the Washington Monument and then immediately about speaking out against slavery. On that line, Jackson steps out of the spotlight. As Kail put it to Jackson, “What happens if Washington's great shame is something that he's aware of and that's unfinished business. He didn't finish it. He allowed everybody to kick it down the road.” Jackson continues, “It instantly felt like, for me as an actor that I justified, I was able to draw a direct relation between Chris the actor and being George Washington.”