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How In the Heights Gave James Monroe Iglehart a Spot in Freestyle Love Supreme

Iglehart has gone from shopping malls to Broadway with this nomadic troupe of improvisational hip-hop artists.

James Monroe Iglehart, Aladdin's original Tony-winning Genie, currently stars on Broadway as Lafayette/Jefferson in Hamilton. He recently finished his run as Phil in the Public Works Hercules, and is now getting ready to periodically jump into performances of Freestyle Love Supreme's first-ever Broadway show.

Freestyle Love Supreme, a hip-hop improv group cofounded by Lin-Manuel Miranda in 2003, has gone through a rags-to-riches journey, and Iglehart has been there for nearly all of it. Since those earliest days, he's become one of the busiest men in showbiz, with a booming career that even ignited the Twitter campaign #NoMoreJobsforJames. But fortunately, in his downtime from social-media warfare, Iglehart caught us up on everything FLS, including the memory of his initiation into the group over a decade ago.

You may or may not be surprised to discover just how many future Hamilton favorites are main characters in that story.

Tony winner James Monroe Iglehart will be one of the regular guest performers in Freestyle Love Supreme on Broadway.
(© David Gordon)

Before we jump into Freestyle Love Supreme, I have to ask how your time with Hercules has been?
Most people know I'm a Disney nerd. When I heard they were going to do it, I immediately ran to Disney and said, "Hey, how can I be a part of this?" I'm playing Phil and having such a wonderful time. The audiences are just as nerdy as I am, and that's what makes it really fun. It feels like a concert. Every time one of the original tunes comes up, people just burst into applause.

You're also still in the middle of your run as Lafayette/Jefferson in Hamilton. How often will you be stopping by Freestyle Love Supreme?
I'm doing a lot. I can't say [how many shows] because we're still working on the schedule. But I've been with Freestyle Love Supreme for 12, maybe 13, years now and it's one of my favorite things to do. It's a project that I enjoy not having to worry about. I've been with the team so long, we're just a family now. It's like going back to camp and just acting stupid with your friends.

How did you find your way to Freestyle Love Supreme all those years ago?
Chris Jackson — the original George Washington [in Hamilton] and now on the show Bull on CBS — he and I have been friends for many, many years. We were doing a show in California and we were backstage and I was just freestyle rapping, and he was like, "Yo man, I can freestyle." So we started freestyling together, and he says, "You need to meet my homeboys up in New York." I thought he was kidding. Then he was like, "There's this dude who can rap about anything." He was talking about Lin[-Manuel Miranda].

Chris Sullivan, James Monroe Iglahert, Andrew Bancroft, Anthony Veneziale, and Utkarsh Ambudkar in Freestyle Love Supreme at the Greenwich House Theater.
(© Matthew Murphy)

We stayed friends and when I was in Boston, he called me and said, "Freestyle is having auditions because Lin and I have to step out of the group for a second to do In the Heights off-Broadway. I think you'd be a good replacement for me." Utkarsh Ambudkar was stepping in for Lin. So I went to the audition, which was basically just performing with the guys in the room. And after about two hours, Tommy [Kail] closes the door and starts talking about schedules, and I looked at Tommy and said, "Are we in the group?" He's like, "Oh yeah yeah, you're in the group." And I've been with it ever since. We've done everything from a 99-seat house at Ars Nova to college tours to performing in malls. And now here we are on Broadway. It's the coolest journey ever.

What has it been like to see Freestyle Love Supreme gain notoriety over the past decade?
It's been so much fun because all of us had nothing when we joined the group. Literally. Except for some skills and a dream. And Lin went on to write In the Heights and Hamilton. Daveed [Diggs] went on to write and star in Blindspotting the movie. Chris went on to television fame. I went on to win a Tony. Bill Sherman is the musical director for Sesame Street. Everybody in our group has done some amazing things. But we were all in Freestyle Love Supreme before all that happened. So we get to not only watch our careers blossom, but every time something cool happens, we all come back to the group with no ego. Coming back to the group is just doing what we love to do.

Are you excited to intersperse your regular run in Hamilton with Freestyle Love Supreme shows?
Totally. Don't get me wrong, I love Hamilton. It's one of the best shows, period. And the cast we have now is just fantastic. But I love jumping up there without a net. I love being able to perform for an audience and making them laugh, and it's fun to just get up there and do it and see what happens.

Freestyle Love Supreme is running at Broadway's Booth Theatre through January 5, 2020.
(© Matthew Murphy)