Hear our full conversation on my podcast “Beyond the Fame.”
Before he originated the roles of Benny in “In the Heights” and George Washington in “Hamilton,” Christopher Jackson got his start with a freestyle rap crew in New York City.
Next week, he brings “Freestyle Love Supreme” to the Kennedy Center from May 10-15.
“Freestyle Love Supreme is a hip-hop improv show,” Jackson told WTOP. “It’s a live stage show. We take short-form games and we musicalize everything. Everything in the show is rapped or sung. It’s just a really unique blend of comedy and heart and makes for a really good time. The best part about it is the audience makes the show every single night.”
That’s right, the audience will write down prompts on their way into the theater.
“We ask for suggestions, be it words, stories from their lives, current news topics,” Jackson said. ‘We take all of that and musicalize it, use short-form games and turn it all into songs. One show could have me climbing on Anthony Veneziale’s back, the next show could have us all playing ferrets running across the stage. You never know what’s going to happen.”
The cast alternates every show, giving you a different set of improvise gurus.
“It’s always a different lineup and that’s the beautiful part,” Jackson said. “We worked really hard to develop a deep bench to open up the group to other artists who had new ideas and new ways to go about doing it. Fortunately, we added some ladies into our ever-expanding crew. They’ve taken the reins and made the show better in every single way.”
The freestyle collective dates back to 2003 in New York City.
“Lin-[Manuel] Miranda, myself, Anthony Veneziale, Chris Sullivan, Thomas Kail … would take breaks when we were developing and workshopping ‘In the Heights’ while Lin was still writing it,” Jackson said. “Before you know it, we were up on stage performing at the Off-Broadway theater Ars Nova, touring the world, playing comedy festivals everywhere.”
Jackson was fresh off his Broadway debut in “The Lion King” in 1997.
“I booked that show 19 months after I graduated college, so that was my first Broadway experience,” Jackson said. “That lasted almost four years and I played Simba for two of those years. I always say ‘Lion King’ was like my grad school. …I was really able to learn what the life was all about, then I left in Spring of 2002 and met Tommy and Lin that fall.”
This led to him playing Benny in the original Broadway cast of “In the Heights” in 2007.
“I thought that every musical-theater composer had to look like Stephen Sondheim or John Kander,” Jackson said. “To know Lin and see what he was doing, I was in disbelief for a long time like, ‘How can this possibly work? He’s young, he’s Puerto Rican, we’re rapping, what is this thing?’ Time would bear it out that I found myself in a really awesome crew.”
He then played the original George Washington in “Hamilton” on Broadway in 2015.
“To be able to lay claim to having spent time with that character for so many people, it’s as gratifying as anything I could have possibly hoped for,” Jackson said. “If I never get to do another thing, I’ve lived several lives in a relatively short amount of time. … It’s worldwide. I’m in the Caribbean and someone just walked past me like, ‘Hey, George Washington!'”
He credits all of the Broadway success back to “Freestyle Love Supreme.”
“I don’t think either ‘In the Heights’ or ‘Hamilton’ are what they are without ‘Freestyle Love Supreme,'” Jackson said. “As creators, there’s only so much you can put down on the page in a rehearsal room. You have to get to know what audiences respond to. The 1,000 performances we logged before ‘Hamilton’ ever expanded … the throughline is there.”
All these years later, it remains an adrenaline rush of spontaneous creativity.
“I am raring to go,” Jackson said. “The beautiful part about doing this show is that it just feeds every other part of your creative nature. It helps me be a better writer, as an actor. There’s nothing quite like doing improv, and there’s nothing quite like making up songs on the spot in front of 2,000 people. It’s just a high-wire act that’s hard to beat.”
Hear our full conversation on my podcast “Beyond the Fame.”
