Mindy Kaling, Omar Epps and 8 More Guest Stars Share On-Set Memories and “Being on the Other Side of the Line”

Vanessa Bayer

The SNL alum rejoins Aidy Bryant as June, a successful, power-suited "she-EO" leading the WAHAM (Women Are Having a Moment) conference that Bryant's Annie attends — which leaves the protagonist walking away with conflicted feelings and without the empowerment she was seeking.

FINDING THE CHARACTER "They just were putting me in these power suits — that's, like, all I was trying on — and they put this blond wig on me, which was such a funny thing. They put these power pink suits and this blond hair on me and I thought, 'I can feel this now, I can really feel it.' A lot of the stuff I was saying was so toxic, but I was saying it with such a big smile — I was trying to sell a lot of toxic stuff with a big smile. It was interesting to try to play that. I was like earnestly, really believing in what I was saying, when a lot of the stuff I was saying was pretty negative."

Omar Epps

Epps joins season four of the time-hopping family drama as Darnell Hodges, father of Malik (Asante Blackk), the boy who's dating Randall Pearson's (Sterling K. Brown) adopted daughter, Deja (Lyric Ross). His role allows for a deeper dive into Malik's upbringing and leads to a tense meet-the-parents dinner opposite Brown.

FIRST DAY ON SET "It's interesting being on the other side of the line. I always look at hit shows like they're a speeding train. I was involved with House, and we had many guest stars and that sort of thing. So for me, being on the other side and now I'm guest starring, it's a speeding train.

"There's a synergy there and you've just kind of got to jump in and make it happen. They were welcoming, but you just don't want to get in the way.

"Everyone has a shorthand and it's not just the cast, it's even the crew. It's just this frenetic energy is moving around you and you're finding your way, but they were so welcoming and inviting.

"I just tried to play my part and enhance that in the ways that I could, so it was cool."

Giancarlo Esposito

Esposito appears in the Star Wars spinoff series as Moff Gideon, the villain going after the internet's beloved Baby Yoda (aka The Child), which leads to a face-off with the Mandalorian. After the big reveal of Gideon's possession of the legendary Darksaber, he will return to the space Western in season two to continue the battle.

LAST SKILL MASTERED "I had to figure out how to allow the Darksaber to be a part of me. It depends upon what we're shooting and what kind of shots, how wide or how close; we use a specific saber to be able to have the right length to fit into the shot of the camera. That saber is intricate and complicated — most of the time it is a [full] saber, sometimes it could be part of the saber. To work with the different sabers, to have them feel like they were coming out of the extension of my personality and my body, was important. I knew how important that was to the fans. Then having to master, not just holding it [and] looking good [while] using it — that's to come, as you will watch soon in this new season of The Mandalorian. I'm very excited to show some of my fighting skills. It's different than holding a knife or a gun; it also has incredible power, so there has to be some reverence for it and to it because everyone wants it. So all of that has to be regarded in my physical and my mental performance in dealing with this wonderful Darksaber that I feel so honored to wield."

Jake Johnson

In a stand-alone episode predating the rest of the show's storyline, Johnson and Cristin Milioti guest star as Doc and Beans, two people who fall in love in a video game store and go on to create the game A Dark Quiet Death before the ultimate demise of their relationship. The '90s-set love story steps away from the central gaming studio for the episode, but ties back in with an appearance from Ian Grimm (Rob McElhenney) at the end.

LASTING IMPRESSION "Mostly when I do TV, I'm so used to the marathon of it all … It was really nice to do TV like an independent movie and say we've got five or six days and then this is over. An indie film is way smaller and you're under the gun with money and time. Rather than a marathon, it felt like a sprint, and that was a really fun way to do television, the beauty of [which] is you do have a little bit more money and you do have a bigger crew.

"With our new media and the new way content is being created, if there are more opportunities like this, it's a dream job because you get to step in, you get to bring everything, you get to go really hard and then you leave the party and they're left to do the rest of the show. So for somebody who doesn't necessarily want to commit to a new family, if you will, it's perfect."

Cherry Jones

The counterpart to Brian Cox's Logan Roy, Cherry Jones appears in the HBO hit's second season as Nan Pierce, the head of her family media dynasty. Nan hosts the Roy family at her property to discuss the possibility of selling her company to Waystar.

FIRST DAY ON SET "[For] the dinner scene in that episode, we were all at the Pierce mansion — the eight Pierces and the eight Roys. It was continuous, everyone was ad-libbing the entire time. The script supervisor would call out someone's name, and that's when they knew that the next little bit of dialogue was being filmed. We never stopped ad-libbing during all the takes. Jeremy Strong had done this research, and he was talking to me and would say things like, 'When you come through the door to the left, that's a Sargent [painting], isn't it?' And I would say, 'It is a Sargent.' And then he would say, 'Well, I was strolling in the garden and I saw this beautiful sculpture, is that actually a Henry Moore?' And I would say, 'It is, I'm so astonished that you know these things,' and he would say, 'Well, we spent a great deal of time in England and my mother's on the board of the Tate Modern.' And he was just bullshitting! My mouth was to the floor because he was brown­nosing me like you cannot believe. Holly [Hunter] was in between the two of us and we were pinching each other under the table practically because we were so delighted by Jeremy's ability to bullshit. I'm sure he'd been at his computer all afternoon coming up with all these references that he could use to butter me up."

Mindy Kaling

Kaling reunites with frequent collaborator Reese Witherspoon to play Audra, an anchor at a rival program to Morning Show, hosted by anchors Jennifer Aniston, Witherspoon and Steve Carell. Audra smells blood in the water after Mitch Kessler's (Carell) sexual harassment scandal and uses it as an opening for a face-off with Aniston and, later, to try to convince another reporter to jump ship.

FINDING THE CHARACTER "I had a scene with Jen [Aniston]. I had a couple of long monologue scenes, but I have a scene where I'm taunting Jen in the bathroom after the scandal happened, and even though it was only a very short scene where I'm pretending to feel bad for her, I felt fully realized in that scene. If you're a competitive co-anchor who feels so comfortable in your skin that you can bully Jennifer Aniston's character in a public bathroom, I feel like you're really confident.

"When I was trying to poach Desean [Terry]'s character, those scenes were great, I felt really in command of it. I felt the storyline of the woman of color trying to poach the man of color from the show because people weren't treating him with the respect he deserved. That was a really unusual and powerful storyline, and I was excited to have it. A lot of my performance came from Mario Lopez, who I absolutely love. He is just so good at what he does — a mix of Mario Lopez and Savannah Guthrie, because they both have great senses of humor and are just so watchable."

Luke Kirby

In a rare three-season guest run, Kirby returns as comedian Lenny Bruce, who continues to be in Midge's (Rachel Brosnahan) orbit as she launches her stand-up career. This season found both Bruce and Midge on the comedy circuit in Miami as he serves as a mentor, of sorts, while she works on her routine.

LAST SKILL MASTERED "The thing that's been the most exciting and exhausting about the role is doing his performances from direct recordings because it gives me this very, very clear blueprint of what he did in these performances. He's often speaking off the cuff, or his thought pattern will shift in the middle of one thought and sort of radiate into a bunch of other thoughts, so listening to that over and over again is sort of taxing and exhausting. Pushing through is really satisfying because once it gets into the body, it's a really fun way to spend the day. Just being an arbiter of this man's work, it's pretty groovy."

Nia Long

Unlike many familiar faces on the Netflix comedy who play themselves, Long guests as Lavette, friend and publicist to Rashida Jones' Joya Barris. She proves to be a sticking point between Joya and Kenya Barris when helping Joya promote her new book, as Kenya grumbles that he doesn't even have a publicist.

LASTING IMPRESSION "I think what Kenya [Barris] is doing is brave, and the Black experience is so diverse and amazing. What he accomplished, in my opinion, was giving audiences something to think about, and that's really important. I think, especially in these times when the world is changing, art is evolving, people are changing, we're seeing things differently, thinking about things differently. So this was a slice of life that, in my opinion, is really funny. It's dangerous and funny and layered and complicated. I just think it's a great show, and I think Rashida [Jones] is fantastic. I love comedy so much. Lately I've been playing more dramatic roles, so it was really cool to just pop in, do something fun, pop out and watch it evolve."

Jane Lynch

Netflix's Steve Carell-led satire features a star-studded cast with a number of big-name appearances, including Jane Lynch as the U.S. Chief of Naval Operations, who assists the incompetent leaders working to establish a sixth branch of the U.S. armed forces.

FIRST DAY ON SET "It was the beginning of the series for everybody, so we had that fresh feel like the first day of school. The room that we got to work in — which was modeled on the actual room where the Joint Chiefs of Staff meet — was just absolutely authentic. The set looked exactly like the room, except of course larger, so that you might [be able to] see it on television. Everybody's uniforms [were] really fun because they were all genuine. I was wearing an admiral of the Navy's uniform with the appropriate medals, and same thing for our Marine guy and the Army and the Navy, and it was really fun to look at everybody in uniform. And [I was] really grateful that none of us were actually in charge in real life."

John Slattery

In an episode of Amazon's anthology series based on the New York Times column of the same name, Slattery and Tina Fey portray a couple navigating a celebrity marriage. The Mad Men star plays an actor who is on the verge of losing his wife, but the two save their marriage after learning to reconnect through games of tennis.

FIRST DAY ON SET "We played tennis first, Tina and me whacking tennis balls around. We're both in the same ballpark tennis-wise, which is playing a few games here and there and trying not to look like a total dipshit, although we were supposed to look lousy and then get a little better, which was fun. We both took tennis lessons from the same guy, but we didn't take them together; we had different schedules before we started, so we took separate lessons. We found these weird tennis courts — who knew there was a tennis court on the top of John Jay College? There were moments where you need to have a good rally for the scene to work, so then there's the pressure — 'All right, let's try and get it back 12 times in a row' — and then you get to around eight or nine and you start to really push it, you're just trying to keep the rally going."

This story first appeared in a June stand-alone issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.