Much has changed since Christopher Jackson last performed in “After Midnight,” a musical ode to Duke Ellington’s years-long engagement at Harlem’s Cotton Club in the 1920s and 1930s, which the Broadway veteran recently revisited for a filmed production at Signature Theatre.

For one, it wasn’t even called “After Midnight” when Jackson first appeared in the big-band revue in 2012, as a part of New York City Center’s “Encores!” concert series: Back then, it was titled “Cotton Club Parade.” Jackson’s second stint with the show, as a two-week guest star on Broadway in 2014, came a year before his career-defining turn as George Washington in “Hamilton.” And that run was two years before he would join the cast of the CBS legal drama “Bull,” on which he has now starred for five seasons.

So when Jared Grimes, the original “After Midnight” cast member who directed and choreographed Signature’s streaming production, reached out to Jackson this spring about returning to the musical, the Tony-nominated actor and R&B singer jumped at the opportunity to approach the material anew.

“Enough time had passed from the last time that I had done it that, in a lot of ways, it was very easy to look at it with a fresh set of eyes,” says Jackson, 45. “I feel as if I’ve lived a couple of lifetimes in the last eight years, given everything that’s transpired. But to that end, this music really resonates when the person engaging with it has done some living and has seen a few more things and has had a few more smiles and a lot more tears.”

Fusing the tunes of Ellington, Jimmy McHugh and Dorothy Fields, among others, with vaudevillian showmanship, “After Midnight” marks the fourth production of Signature’s five-show virtual season, filmed under coronavirus safety protocols. Playing a different role this time around, as the show’s emcee, Jackson frames the vibrant proceedings with snippets of Langston Hughes’s poetry while also performing several songs, including Harold Arlen and Ted Koehler’s “I’ve Got the World on a String.”

And it’s not the only musical Jackson recently returned to on screen: He also makes a cameo in the film adaptation of the Lin-Manuel Miranda-scored “In the Heights,” having originated the role of Benny on Broadway in 2008. In a phone interview last week, Jackson discussed “After Midnight,” “In the Heights” and how both works feel as timely as ever in 2021.

This interview has been edited for length and clarity.

Q: What made you interested in returning to "After Midnight" for Signature's filmed production?

A: It’s obviously a great show, and I kind of always had my eye on the emcee role in the show, but had seen it done beautifully by Dulé Hill, and then also by Josh Henry. So getting to take a stab at it was fantastic. And once we figured out what the shoot would be, I headed down to D.C. and knocked all of mine out in a day. It was pretty spectacular to be thrust into this amazing company of actors.

Q: How did the experience of preparing remotely and filming your role so quickly shape your performance?

A: A lot of what is captured in that film is not rehearsed. A lot of what is captured in that film is me reacting to the music and reacting to the other actors and reacting to the ideas, the seeds that Jared planted in my head as we were approaching time to shoot. What they did and what Signature did was really just facilitate me engaging with this work in real time.

Q: What was your approach to reciting Hughes's poetry?

A: I think there was a beautiful resonance between Langston’s words and where we find ourselves currently in our society. And, really, I wish that it was more of a contrast, but it’s really not. Great, great words and great poetry find their meaning and find their resonance in every age, whether things have changed or whether we just think they’ve changed. I think that’s certainly true for the words that were shared in this piece.

Q: Having now seen the "In the Heights" film, what did you think of Corey Hawkins's performance, filling your shoes as Benny?

A: Corey is an amazing, amazing performer. We’ve all seen his brilliant work in other films, and the thing about the roles that Lin writes for me, they’re never as easy as they may seem. And I thought that Corey did a brilliant job. He brought heart and he brought enthusiasm and a beautiful singing voice, and he’s an amazing actor. I can’t do anything but be proud that I played some small part in what ultimately became his performance, simply because I was there first.

Q: How did your cameo role in the film as the Mr. Softee ice cream truck driver come about?

A: Well, it came about because Lin said, “Hey, come on Tuesday.” And I said, “Yes.” [Laughs] Obviously, Benny is not a role that I’m any longer able to do, but to be able to participate in any way is a great thrill for me because back in 2002, when I met [Miranda], we never imagined that this is where we’d be. I wish that I had more of a role to play in the movie. I would have been a [production assistant] on the movie just to be around. But I’m genuinely just proud. In a time that we’ve been sequestered and separated for almost two years now in fear, and losing loved ones, what better time is it for a show like “In the Heights” to come around that reminds us all why we love neighborhoods and why we love each other?

After Midnight

Signature Theatre. sigtheatre.org.

Dates: Through Aug. 4

Prices: $35.