Emmys: Jon Hamm Reveals His Major Oops Moment on Set of 'Kimmy Schmidt'

Courtesy of Netflix; AP Images

And that's just one funny story recalled by 14 A-listers — from Jennifer Hudson on 'Empire' to Laura Prepon on 'Orange Is the New Black' — who made guest star appearances on various shows this season.

This story first appeared in a special Emmy issue of The Hollywood Reporter magazine.

THR asked: What was the funniest or most challenging moment you had while filming your guest role?

Sasha Alexander
Helene Runyon, Lip's college professor on Shameless (Showtime)

"There was a scene that was written where I am postcoital and dressed in a tank top and bottoms. But when I got to set, the director, who was a woman, decided she wanted to start it at the orgasm, with me nude and on top of Lip [Jeremy Allen White]. She wanted to see all of it. And it was eight in the morning. Super-sexy hour. I kind of gulped. I just wasn't ready because it was on paper one way, then all of a sudden, it's like, 'Take it all off and go!' I wasn't prepared. That was the moment when I thought, 'Oh, I'm definitely not on [my show, TNT's] Rizzoli & Isles.' There was a discussion, and we negotiated it down to a very sheer tank top. Jeremy held my hands through most of it. Emmy [Rossum] gave me some lovemaking advice. It's really not printable, but one of the tips involved throwing your head back. And [actor] Steve Howey offered me a shot of cherry vodka. At 8 a.m. I'm not sure it helped, by the way."

Jon Hamm
Richard Wayne Gary Wayne, who held the "mole women" captive on Unbreakable Kimmy Schmidt (Netflix)

"The series of flashbacks on the reverend's secret videotape were pretty challenging. Not only were they ridiculous, culminating with me humping the couch, but those were the last setups of the show. Everybody was wrapped, and I was there with the crew, who'd been working together for 13 weeks. I was the new guy going, 'Sorry, everybody, I'll try to get these done fast.' There was a lot of pressure. I figured the more ridiculous I was, the better, and they provided me an excellent opportunity to be ridiculous with a capital 'RIDIC.' When I was doing the karate, I was like, 'I think I'll do a kick and the flip-flop will come off. That'll be funny.' They were like, 'Just don't kick it into a light.' I'm like, 'Come on, what am I, an idiot?' And of course, on the first take, I kicked the flip-flop right into a fluorescent prop light and shattered it all over the place. That was super great."

Marcia Gay Harden
Hannah Keating, Annalise's sister-in-law on How to Get Away With Murder (ABC)

"Guest-starring on Murder essentially feels like joining the game Clue. Suddenly, there's this new character put into the game, and no one knows anything about her, including me. And when you'd ask the writers, they might go, 'Not quite sure.' It was figuring out how to be in that world with the information I had and make it make sense to me. At some point, you think, 'Let me just go in, have fun and make the moment honest. I'm just going to be as fierce as I can be playing what the writers have given me' — which was crazy-emotional scenes with Viola [Davis, who plays Annalise]. She and I created all this backstory for our characters, and it was exciting. The show is very intense, yet people are having a good time."

Jennifer Hudson
Michelle White, a music therapist who works with Andre on Empire (FOX)

"The toughest was the 'Let's pray' scene. People are like, 'I've never seen a prayer like that!' Michelle and Andre [Trai Byers] have a professional relationship, but it's clear in that scene, there's an attraction. She's trying to remain professional, and I'm trying to be in the moment with the character, sing and play the piano at the same time. The dynamic of those three things was kind of confusing. I'm not a piano player. I know the basics. I can play in the key of C. But the song ['Remember the Music'] was very intricate. I was trying to figure out the whole configuration of the timing of the piano and sing in a different rhythm from what the piano was doing. I'm always holding my breath from when they say 'action' up until I'm done. Then it's like, 'Did I do it? Is the director happy?' That day, I felt like we had a good chemistry between Michelle and Andre. It felt authentic. It felt right."

Margo Martindale
Claudia, Elizabeth and Philip's former KGB handler on The Americans (FX)

"I was nervous about meeting [actor] Frank Langella. Before this season, the only people I'd worked with on the show were Matthew Rhys [Philip] and Keri Russell [Elizabeth]. So it was a whole new world. And I did have a little bit of 'he's taking my place' feeling because he's Philip and Elizabeth's handler now. But that was all instantly gone when I met Frank. We went in to rehearse, and I just adored him. He's a theater person, and so am I. We had just one small scene together, but wasn't it a good one? It was one where there was no hidden agenda, something you rarely see on this show. But my character and his are friends from Russia who grew up together in the KGB ranks. That relationship was really fun to bring to life."

Rita Moreno
Sofia, Rogelio's mother on Jane the Virgin (The CW)

"Some of the funniest moments happened because they let me improvise a lot. When the scene was over, I'd just keep on prattling. My character, Sofia, was supposed to turn to the grandmother, Alba [Ivonne Coll] and say, 'You look wonderful,' and she says, 'Thank you.' There was no more dialogue, so I instead said, 'Well, what about me? How do I look?' And of course she's forced to say, 'You look wonderful.' And I said, 'You really think so?' I just had a handle on the character. Sofia's so self-involved. It was fun speaking what I felt was in her mind. I've known ladies like that who are all about themselves, especially in show business. I called her look 'bad Beverly Hills.' There were too many things all over her. It was like how Elizabeth Taylor looked when she married that last time, to that fool [Larry Fortensky]. That was like Sofia."

David Hyde Pierce
Frank Prady, Alicia's political opponent on The Good Wife (CBS)

"The most challenging thing was, I didn't know where the story was going. In all those years of doing Frasier, you always knew what the story was in that half-hour episode. And I do theater a lot now, and when you do a play, you know the play's arc. But doing The Good Wife, I never knew from episode to episode who the character was or where he was going — right to the end. I didn't find out until I got the script for my last episode, basically the night before we started shooting, that my character wasn't going to win the state's attorney election. Then when I went to shoot that day, Julianna [Margulies] says, 'Actually, I'm going to have to withdraw, so you'll end up winning anyway.' It was very moment-to-moment but also liberating because all I could do was trust the writing, which was magnificent. It was a different way of approaching a character for me, and I ended up loving it."

Laura Prepon
Alex Vause, Piper's ex-lover (and former drug trafficker) on Orange Is the New Black (Netflix)

"My character is usually very composed and doesn't show when she's vulnerable. Playing the paranoia of the kingpin being after her was challenging. The first scene in Alex's apartment, someone knocks pretty aggressively, and I had to grab a knife. The first knife I grabbed was a huge butcher knife, and we all started laughing because it looked like I was in a horror-slasher movie. The director correctly chose a smaller one, and Alex used that to protect herself before upgrading to a gun. Alex's parole officer's name was Davey Crockett, 'king of the wild frontier.' So I'm holding the gun, and in walks my parole officer. I have to be really scared and know I'm busted and probably going back to prison while having to say 'Davey Crockett.' There were many takes where I'd start laughing. It was funny, but it turned out well."

Michael Rapaport
Lenny, Louie's annoying cop friend on Louie (FX)

"The most challenging scene was when my character, Lenny, has a breakdown over losing his gun. The screen direction said, 'Lenny is acting like a wild animal.' It was obvious that [creator-star] Louis C.K. wanted it to be extreme and highly emotional. As an actor, you can only do something like that a couple of takes at the same level. You can do it in a fake way and get by, but I wanted it to be as genuine as possible. I wanted to live up to the potential of what was on the page. Louis wanted to do it all in one take, so we had to really map it out and be conscious of blocking, or you wind up doing it 15 times because you screwed up the camera. When they were setting up the lighting, I talked to the cameraman like, 'All right, I'm going to come here then I'm going to push the table.' I remember Louis told me, 'I'm not saying much to you because I feel like you've got everything under control.' He creates an environment where you feel very encouraged and trusted, and I always feel like I do my best stuff when I'm in that kind of place. That night, I slept good. I was proud of myself. It was a good day's work, and I gave it my all."

Corey Stoll
Sandy Bachman, Carrie's Pakistan station chief on Homeland (Showtime)

"I understood why the producers cast me: It might build expectations in the viewer that I'd be sticking around. It was a bit of audience manipulation to set this character up as perhaps a big part of the season, and then suddenly, he's gone. I wanted viewers to feel that I was a character who had a history and a future. That he, Sandy, was an ambitious and youngish station chief parallel in some ways to Carrie [Claire Danes]. This was a challenge. Not only was it a small role, but for a lot of it, I didn't really speak that much. That whole sequence where I'm going to meet my contact, and the realization that I've been set up and my cover's been blown, felt almost like a minimovie. As a guest star, you rarely have a chance to be the protagonist. You're usually just there to push the protagonist into action. So that was really great. I was excited to be a part of that show, even for just a little while."

Bradley Whitford
Mark/Marcy, Maura's longtime friend on Transparent (Amazon)

"Is it terrifying to dress up like a woman when dressing up as a woman is not part of your personal experience? Yes. I've never been more nervous about a costume fitting. It's extraordinary to me how painful heels are but also how instantly I got an ego about what they did for my legs. The costume people said, 'You have nice legs,' and I'm like, 'You know what? I think we should bring the hem up a little. And bigger heels.' To prepare, I was reading this book called Cross-Dress for Success, and my son, who's a freshman in high school, walks into the kitchen and was like, 'What the f— is this?' I was like, 'You know what? Daddy's working, and you're welcome.' Doing this show was very important to me. I have transsexual people in my family. I wanted to make sure I could remain a complicated human being for the audience beyond just being a guy in a dress. But it wasn't always precious on set. Before one take, Jeffrey [Tambor, who plays Maura,] and I were tugging at our bras and yanking at our panty hose, and I'm like, 'You think this is going to be the scene they use in our "In Memoriam" reel?'"

Steve Zahn
Ronnie, Claire and Phil's neighbor on Modern Family (ABC)

"Being a guest star is like being a substitute teacher coming into a class that's been together all year. It's difficult, especially if you're jumping into a well-oiled machine like Modern Family. On top of that, it's almost like you're doing live theater. They move so fast. You're not covering it the normal way; you're not doing a two-shot or three-shot and then popping in for singles. I remember the first scene I shot, it was over before it started. They were like, 'We got it!' I'm like, 'You did? Where was the camera?' Artists are all insecure, so I'm thinking, 'It's been a long, good run, but it's about time someone figured out that I suck.' Luckily my character, Ronnie, was right up my alley. He's a guy with a truck and a lot of toys in his garage, he's really talkative and crazy. What you see is what you get. Minus the pot, it was basically me. I'd rather have good Kentucky bourbon."