5 Iconic Christopher Jackson Moments to Celebrate His Return to Hamilton

Here comes the General! Nearly 10 years after taking his final bow in Hamilton, original Broadway cast member Christopher Jackson will return to the hit hip-hop biomusical from September 8 through January 3, 2027. George Washington's going home to the Richard Rodgers Theatre, and we're celebrating by revisiting our favorite pop culture moments featuring the presidential powerhouse. Sit under your own vine and fig tree and check out these clips while you wait for it.

1. His first George Washington reprisal

It seems Jackson is drawn to Washington like a moth to a flame. The proof is in the parliamentary pudding: Jackson’s And Just Like That... character, political candidate Herbert Wexley, dressed up (well, down) as Washington in a cheeky nod on the Sex and the City spin-off. While he won’t be wearing the powdered wig on stage, it’s something to tide you over until his highly-anticipated return.

2. Doing his best Justin Bieber impression on Sesame Street

You read that right. In 2011, Jackson appeared on Sesame Street in Muppet form not as himself, but as the then-teen superstar Justin Bieber, singing a parody of his 2010 hit “Never Say Never.” The rewritten “Measure, Yeah, Measure” was not the Sesame Street song which won Jackson an Emmy, but it did teach children everywhere how to use a ruler. Jackson is now halfway to the illustrious EGOT status after his Grammy win as a principal soloist on the Hamilton original Broadway cast recording.

3. That “Louder Than Words” tick, tick… BOOM! cameo

Hamilton creator Lin-Manuel Miranda made his feature film directorial debut with 2021's tick, tick… BOOM!, an adaptation of Jonathan Larson’s semi-autobiographical musical. Sprinkled throughout the film were surprise cameos from theatrical legends, including the voice of Stephen Sondheim just weeks before his passing. Jackson can be seen in the film’s final number, “Louder Than Words.”

4. “One Last Time” at the White House

If President Obama calls what you’ve just performed “magic,” you’re set for life. Jackson’s rendition of “One Last Time” in the White House might not have been totally in character—George Washington was the only U.S. president who never lived in the White House—but we’ll let a little inaccuracy slide for this history-making performance. Take it from Obama: this interpretation is not to be missed.

5. My BFF LMM

Jackson met Miranda in 2002 during the development of In the Heights. Since then, they’ve been besties for the resties. If Miranda saying, “I don't know about God, but I believe in Chris Jackson,” while accepting his first Tony doesn’t solidify a life-long friendship, we don’t know what does! The frequent collaborators have six projects together to date: Jackson played Benny in the original Broadway cast of In the Heights, and later had a cameo appearance in the 2021 film adaptation. While rehearsing for In the Heights, the improvisational hip-hop group Freestyle Love Supreme was born, with Miranda and Jackson as founding members. Jackson can also be heard in Moana as the voice of the titular heroine’s father. Now that Jackson is returning to Hamilton, it’s only right that a certain Pulitzer Prize winner tags along. Your move, Miranda.

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