When Daveed Diggs first strutted onto the stage at the Richard Rodgers Theatre, he wasn't just playing a historical figure. He was basically rewriting the rules of how we look at the Founding Fathers. If you've seen Hamilton, you know the moment. The lights come up for Act Two, the jazz starts pumping, and there he is—draped in enough purple velvet to make Prince jealous.
It’s iconic.
But honestly, the connection between Thomas Jefferson and Daveed Diggs is way deeper than just a flashy velvet suit and a fast rap. Diggs didn't just play Jefferson; he interrogated him. He took one of the most brilliant, complicated, and—let's be real—problematic men in American history and turned him into a high-speed, lyrical antagonist.
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The Rockstar Entrance: Why Jefferson Sings Jazz
One of the coolest things about the way Lin-Manuel Miranda wrote the show is the musical "age gap." Everyone in Act One is rapping. They’re the young, hungry, "scrappy and hungry" revolutionaries building a world from scratch. Then comes Jefferson. He’s been in France. He missed the war.
While the rest of the characters are moving at the speed of hip-hop, Jefferson enters with "What'd I Miss?"—a song rooted in boogie-woogie and jazz. Diggs has mentioned in interviews that this was intentional. Jazz is the "older" music in the world of Hamilton. Jefferson is the old guard, the landed gentry, coming back to a country that’s already moved on without him.
It’s a flex.
By having Diggs perform this role with such a preening, rockstar energy, the show highlights the disconnect between Jefferson’s lofty ideals and his actual life. He’s singing about home, but home is a plantation. He’s talking about liberty while handing his bags to a slave. Diggs plays that tension perfectly—he makes you love him even when you know you shouldn't.
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The Fast-Twitch Muscles of Daveed Diggs
Before he was a Tony winner, Daveed Diggs was a track star at Brown University. He actually broke the school record in the 110-meter hurdles. You can see that athleticism in his performance. Whether he’s leaping off a desk or firing off syllables at a breakneck pace, there’s a physical precision that most actors just can’t touch.
In "Washington on Your Side," Diggs hits some of the fastest lyrics in the entire show. We’re talking about a level of technical skill that comes from his background in experimental hip-hop with his group, Clipping. He wasn't just a Broadway actor learning to rap; he was a rapper bringing a specialized toolkit to the theater.
Breaking Down the Suit
Let's talk about the look. Costume designer Paul Tazewell did something brilliant here. While Alexander Hamilton wears green (the color of money and newness), Jefferson is in magenta. It’s meant to evoke "old money" and royalty.
Diggs has said that the costume helped him find the character’s "fabulousness." In the first act, he plays the Marquis de Lafayette with his hair pulled back in a tight ponytail, mimicking the 18th-century "queue" but with a modern twist. In the second act, as Jefferson, the hair is let down. It’s "explosive," as Tazewell put it. It’s a visual representation of Jefferson's ego.
Dealing with the "Sally" Elephant in the Room
It’s impossible to talk about the Thomas Jefferson Daveed Diggs portrayal without touching on the historical reality of slavery. This is where things get tricky. The musical has faced criticism for "glossifying" the Founding Fathers, and Diggs hasn't shied away from that.
He’s been very open about the fact that he disagrees with almost everything the real Jefferson stood for. He told Time magazine that he had to embrace the contradictions. He’s playing a man who wrote "all men are created equal" while owning hundreds of human beings.
There’s a moment in the show where Jefferson asks "Sally" to open a letter. That’s the only real nod to Sally Hemings. It’s a "blink and you’ll miss it" line, but in Diggs’ hands, it feels heavy. He plays Jefferson as a man who is so comfortable in his privilege that he doesn't even see the hypocrisy. That’s what makes the performance so effective—it doesn't try to make Jefferson a hero. It makes him a politician.
Why it Works (and Why We're Still Obsessed)
Usually, when you learn history, it feels like looking at a dusty oil painting. Static. Boring. Diggs changed that. He made Jefferson feel like someone you’d see in a modern-day cabinet meeting—someone who is incredibly smart, incredibly petty, and very aware of his own brand.
The rivalry between Hamilton and Jefferson in the show works because Diggs is a genuine match for Lin-Manuel Miranda. In the Cabinet Battles, they aren't just debating debt limits; they’re battling for the soul of the country. Diggs brings a "sassy" (as fans call it) energy that makes the intellectual debate feel like a high-stakes sport.
What You Can Take Away From the Performance
If you're an actor, a creator, or just a fan, there’s a lot to learn from how Diggs handled this role. He didn't just "act" Jefferson; he interpreted him through his own lens.
- Use Your Unique Skills: Diggs didn't hide his rapping background; he leaned into it to make the character faster and sharper.
- Lean Into the Contrast: He played the "villain" (or at least the antagonist) with so much charm that you can’t look away.
- Acknowledge the Flaws: By acknowledging that Jefferson was "pretty sh—ty" in real life, Diggs was able to play the character with more nuance rather than trying to be a "good guy."
Diggs left the show in July 2016, but his version of Jefferson is the one burned into the public consciousness. It’s the gold standard for how to take a "stodgy" historical figure and make them feel electric, dangerous, and undeniably human.
If you want to see the technical mastery for yourself, go back and watch the Cabinet Battles on the Disney+ recording. Pay attention to how he uses his hands, how he modulates his voice, and how he never stops moving. It’s a masterclass in character work that proves history is only as boring as the person telling it.
Check out Daveed's work with his band Clipping to see where that incredible lyrical speed actually comes from. It’ll give you a whole new appreciation for the "Cabinet Battle" flow.