Cal Penn's busy year includes roles as Dr. Anna Nicole Smith, Greg Araki and Harold & Kumar 4 in the credits: "One of the funniest scripts ever."

After years of political juggling and activism, endorsing the likes of President Obama and New York Mayor Mamdani, Cal Penn is back to manhood. A day after finishing his role in the film "The Decline of the Damned Western Civilization" by Greg Araki, Deadline spoke with the actor about his busy year in cinema, which was with […]

After years of political juggling and activism, endorsing the likes of President Obama and New York Mayor Mamdani, Cal Penn is back to manhood.

A day after wrapping up his role in Greg Araki's Decline of the Damned Western Civilization, Deadline spoke with the actor about his busy year in the movies, culminating in his role as Dr. Sandeep Kapoor, Anna Nicole Smith's late doctor.

I was really more drawn to Sandeep's insecurity, and vulnerability, and this push and pull between—I think five times in the movie, he says, 'I'm just a private person, I have a private life,' but then he makes every decision against that, just for attention, right?" Penn explained. "So there was that kind of freshness to the character that I hadn't played before that drew me to it." Watch on Deadline

Based on Kapoor's 2017 memoir Trust Me, I'm a Doctor: My Life Before, During, and After by Anna Nicole Smith, the biographical film chronicles the doctor's economic and professional relationship with Smith as his patient, which goes unrecognized when they begin a brief friendship outside the exam room before she dies of a prescription drug overdose.

Although the Medical Board of California opened an investigation into Dr. Kapoor for prescribing methadone to Smith, alias Smith, when she was eight months pregnant, he was acquitted of all legal charges. Smith died and was allowed to continue practicing medicine.

While preparing for Briarcliff, Penn found that "the real Sandeep, to my surprise, was so welcoming that he let me shadow him and follow him."

I dined with him many times and I think I saw a few things that made me think. There are things he does physically. He sits differently depending on who he is with. If there is someone who is obviously nervous in front of them, they will sit very differently than friends or family with whom they are comfortable. The way he speaks and speaks is not based on his flashy codes either. "He's around."

Kapoor's retelling of his experience with Anna Nicole also included a guerilla-style scene shot in the middle of the 2024 West Hollywood Pride Parade, reminiscent of 2005's Viho.

"Ten, our director, basically had 30 background artists surrounding this car, and shot by shot, it had to look like Anna and Sandeep's actual parade, so everything else in the background is mostly out of focus, unless you can get rid of the few things left over from 20 years ago, like the circus of books," Penn noted. "But it was fun because you only had one shot, right? You start at the beginning of the parade and work your way to the end and hope you get everything you need."

And while Larry Birkhead, the father of Anna Nicole's daughter Danielleen, has spoken out, Penn disagrees with the project, acknowledging that "it's not going to be a movie for everyone," but acknowledging that "someone died tragically, and I never want to trivialize that in a movie."

Coming to the end of a busy year, which included a "fun" arc as "Someone Terrible" in Season 4 of the BBC/HBO industry, Penn is preparing to return to his roots following last year's news of a fourth Harold and Kumar from writers John Horowitz, Hayden Schlesberg and Jashal.

"So John Cho and I are officially signed on for the fourth movie," Penn confirmed. "John and Hayden, amazing screenwriters who wrote all three movies, they directed the second movie, they're directing the fourth, and they finished the script that John and I both read a few weeks ago, which I loved. It's followed by three more movies, and I'm not just saying that because I'm playing the guy, but it's one of the funnest times."

Penn added, "So I'm excited, but it hasn't been greenlit or anything, so I don't have any real updates, other than I read the script and I loved it. So hopefully we can make it."

Penn, meanwhile, has been considering a bucket list item after working with New Queer Cinema director Greg Araki on his next film, The Decline of Fucking Western Civilization, a role he told his agent to "pursue aggressively" after he first saw Araki speak after a screening of his film Doom Generation at UCLA in 1995 during Penn's undergraduate days.

"I didn't know anything about film, you just walk in," recalls Penn. "It's like nothing I've ever seen," I say. And then I listen to his Q&A about his kind of guerilla filmmaking and shooting in Los Angeles and just doing things the way he's always done them. So, I was excited to join the cast and I just packed up."

Read about Cal Penn's experience playing Dr. Sandeep Kapoor in Trust Me, I'm a Doctor, now in theaters, as well as his upcoming roles in Harold & Kumar 4, Greg Araki's The Decline of Fucking Western Civilization, and more.

DEADLINE: What was it about this vision of Anna Nicole's story that appealed to you?

Kal Penn: So, I didn't know much about his story, and if I'm being honest, I still don't because the arc of Sandeep's role in the film kind of starts from before he meets Anna until after she dies. And so, I never researched him because that made me Sandeep. And then you roll a film, and you say, "Okay, that's it." ... But the reason I said yes to the movie is, I remember being a young actress in Los Angeles, in the early days of reality TV, and I think there was a party that I went to, like an awards show, that Anna was at, but she was there with like four cameras and a huge crew, and it was obvious that she was filming a reality show. But I remember my friends and I being like, "Oh, is he on a reality show because he's acting like that or is he acting because he's on a reality show?" And this is a question that the film does not fully answer either, it is an open question until the end of our film. But that was all I knew about him, right? It's like, "Oh yeah, Anna Nicole Smith is from that reality show." So, I see that the email came from my agent for this movie, and there was a short logline that I just skimmed, and then the script was attached. And as I click on the script, I think to myself, “Oh, yes, I know this story. It is about a doctor who is in prison for the murder of Anna Nicole Smith. And then I started reading the script, I was like, “This was no accident at all. How do I think this happened?" I never followed the case or anything, but why do I think this happened? And then I said, "Am I one of these people who reads three tweets and thinks I'm an expert on something?" So, I read the script with that in mind, and I was really more drawn to the insecurity of Sandeep's character, and the vulnerability, and this push and pull between—I think five times in the movie, he says, "I'm just a private person, I have a private life," but then he makes every decision against that, just for attention, right? So there was that kind of freshness to the character that I hadn't played before that drew me to it.

Deadline: How was your physical change and voice change for the role?

Penn: Obviously, Anna Nicole Smith was in the public eye as a character. Sandeep is an interesting character to play because he wasn't like that. I guess he's been in the public eye, and so fair play and all that, but he's not like a household name, and I think the biggest decision in trying to figure out with Thane, our writer and director, how to play him right was, "I just have to surprise these vulnerabilities and these poor moral decisions in something bigger than what's in my script." Let me shadow him, follow him. I dined with him many times, and I think I saw a few things that made me think. There are things he does physically. He sits differently depending on who he is with. If it's someone you're visibly nervous around, they'll sit very differently than friends or family they're comfortable with. The way he talks and his glamour, too, not that he's code-switching, but they clearly change based on the people around him. So there was a bit of the Alexander Technique, there was a bit of background to base it all on, but that's what happened in the transformation. Not necessarily, because to me, the things you learn about him based on everything made a lot of sense.

DEADLINE: It's funny you bring that up because that was one part of it that I really resonated with, his experience as a closeted gay man, and that scene in the West. The Hollywood Pride Parade really made me happy, just seeing it through his eyes, not just being friends with Anna Nicole, but being around all these people who accept him for who he is, and I'm curious what it was like shooting that scene for you?

Penn: That scene is interesting, especially hearing your take on it, because in reality, Sandeep told me that he went to the Abbey several times with his friends, always had a good time, but generally felt invisible in that space. Therefore, children did not come to him to talk to each other. Some of that might be because he's a nerdy brown doctor, and Weiho was especially fairly homogenous back then, the standard of beauty was so different. It still is, but thankfully less so than 20 years ago. So what he told me, and this actually ties into the earlier part of getting to know him a little bit, when I first shadowed him, something called out. I went to his office, it is still in the valley, the same as the previous office, it is small. And when you walk in, there's like three receptions, and its little waiting room, and then maybe three exam rooms. Glenn, I don't know about you, but when I make an appointment to see my doctor, I'm either talking to a goddamn AI bot that makes my blood boil, or I have to log in and pick a slot. And in both cases, there are no appointments for seven and a half weeks. So when I saw Sandeep's way of working, and there's a human who picks up the phone and he knows everything about his patients... It was that personal touch in 1950s medicine that I immediately realized, "Well, it's not strange that Anna invited him to Pride," because it was common for him to get an invitation to your patient's bar mitzvah party or Super Bowl party. These were just things that happened. So, when Anna invited him to the Pride Parade and then to the Abbey, it only made sense that he would go. What didn't make sense is that you can have two champagnes with your patient/acquaintance. Don't have a bottle of champagne with her and then treat her on the couch next to the dance floor. These are objectively terrible decisions, right? So, I think knowing all of that and then knowing in the real world, that was very fundamental for me because I knew that the real Sandeep was in the Abbey and he was enjoying it, but the way that he was experiencing it through Anna's lens, it was clear to him that he was getting all these people's attention because he was around her and she knew that he was in her orbit. But that night was so intoxicating that it was fun for me, it was sad, it was heartbreaking. There was also no sympathy for someone who made bad decisions. It was all those things, it was a night in an abbey, you know?

Deadline: Yes. Did you really shoot Abby?

Penn: No, we shot most of the movie in Toronto, so it was a nondescript club in Toronto. The only thing we shot in the states, in Los Angeles, was the Pride Parade stuff.

DEADLINE: Yeah, I was going to say I saw you all going through the circus of books. Was it really filmed at the Pride Parade?

Penn: Yeah, it was guerrilla style, so Tan, our director, had basically 30 background artists surrounding this car, and shot by shot, it had to look like Anna and Sandeep's actual parade, so everything else in the background is mostly out of focus, unless you can get rid of the little things that are left over from 20 years ago. Which was super cool because you only had one shot, right? You start at the beginning of the parade and work your way to the end, hoping to get everything you need.

Deadline: How was filming the makeup/vomiting scene, because it looks like it might have gone wrong.

Penn: It was interesting. I mean, it was one of those scenes where it's 7:30 in the morning in a dark club in Toronto. I know the story everyone wants to hear is, "Did you have a good night?" Yes, we were having fun. It is exactly like brushing your teeth first.

DEADLINE: It broke my heart that she had to come out publicly to save her career, but it made me happy when she finally came out to her father. Tell me about exploring that dynamic.

Penn: It's funny, a lot of people ask about that dynamic. I find it interesting because it's not as compelling to me as the terrible decisions he made. I understand why we have it in the script, because you need something personal to flavor it. Otherwise, it's a legal drama, but the parts leading up to that might culminate with the scene with his father, there are several scenes I have with Linda Hamilton, where I, as Sandeep, withhold important legal information from my defense attorney, like, "Why are you doing this?" And it shows you the psychology, he thinks he's doing the right thing. So no matter what mistakes he makes, and I think I have it there now and the audience sees it, they watch it, they're like, "Don't make that decision, I'm watching a train wreck, I'm going through a car accident on the 405, I know that's going to be a bad decision. I know you're making that decision. I wish you wouldn't go there, yeah. It's like, with Derek Why does he think it's the right thing to do? I remember asking him, "Why did you take the files home from your office?" And foresight... "It's two things," says Sandeep. One, probably shouldn't, is obvious." But he had paparazzi posing as patients and coming to his office and trying to get him an appointment. And he really believed that they were going to come in, come in in the middle of the night, and steal Anna's files, and all her medical information would be out there. And I was just like, "Yeah, but the only other choice was to take the files home?" I'm like, "Brother, it doesn't add up. Those aren't the only two choices in life, are they?" So to me, it's the way he talks himself into this circle of poor decision-making that I never thought would be for him, lie upon lie upon lie. And I think in looking at his relationship with his father, you can see the weight it had on him. In real life, if I remember it correctly, the real Sandeep was very open with his mother and with all his friends, and so creating that relationship with his father and parents was, I think, a bit more creative freedom for the film for Thane. It's also why I think I gravitate so much towards the bad decisions she made with her vulnerability, versus anything about identity, whether it's ethnic identity or gender identity or whatever.

Deadline: I'm curious if you've seen Larry Birkhead's response?

Penn: You know, I didn't really think about it, just because I think I was so focused on trying to bring Sandip to life. I also know very little about the real Anna Nicole Smith. I think the only thing that mattered to me was that someone died tragically, and I never want to downplay that in a movie. So, I remember asking you, “This is kind of pitched as a dark comedy. I hope there is no comedy in the tragic death of this woman." "No, no, no, of course not," he says. And then you read the script and you see that dark comedy comes from Sandeep's self-deprecation, but of course I mean, people are going to have their own opinions about that. This movie isn't meant to be for everyone, and so if there are people who feel this is disturbing for whatever reason, I'm not the guy to say "you should see it anyway." You should skip this one.

DEADLINE: I know someone was talking about Harold IV and Kumar a while back. Is this happening?

Penn: Yeah. … So John Cho and I have officially signed on for the fourth movie, which I think Deadline reported on a few months ago. John [Horwitz] and Hayden [Schlossberg], the amazing screenwriters who wrote all three movies, they directed the second movie, they directed the fourth, and they just finished the script that John and I both read a few weeks ago and I loved it. It tracks with three other movies, and I'm not just saying that because I'm playing the guy, but it's one of the funniest scripts I've read in a long time. ... You can't make a movie like that unless it's humorous and reflective of what's going on in the world, in a way that I think only John Horowitz and Hayden Schlossberg could write, and I just thought it was very cleverly done with just the right amount of silly jokes that always come with Harold and Kumarchit movies, so I'm still doing it. No real updates, other than I read the script and loved it. So hopefully we can make it. I usually text them once every two and a half, three weeks and say, "Update?" So, I will do that this afternoon.

DEADLINE: I love this franchise and I'm curious, are you and John Cho willing to continue this franchise to the grave? We see Cheech and Chung still there kicking it.

Penn: You should ask John what he thinks. I can tell you that over the years, I think after the second movie started, I was basically like, "Oh my God, what chance do I have that I'm going to be able to make this kind of thing?" I used to love comedy, obviously not comparing Harold and Kumar to something I respect, but one of the things I loved about John and Hayden's brain writing was that it almost reminded me of… One of the reasons I loved the Muppets, and never lost my love for the Muppets in later years, is that some of the early jokes in The Muppet Movie are there. Then there are other things for kids. And I think what they're doing with these movies is if you just want to go in with your friends and laugh, which is ultimately the goal, regardless of the humor and commentary, the number one goal of these things is always to make everybody laugh. You laugh and have fun with your friends, and if you want to find humor in it and love it, obviously there is for you too. So, I kind of loved it and I was like, "I feel lucky that I started with what we made, we made three of them. If we make 50 of them before I die, we'll be happy." I just think the character is also a lot cooler than I'll ever be, and especially as the world has become more and more polarized, that's one of the things I love about those characters is that they mean so much to me. I've talked to John and Hayden about this and they feel the same way. It means a lot to us that people across the political spectrum enjoy it, and it's really cool, that in a world where we have relatively few things that we can do together, I love that food, comedy, movies, music, those are still things that can have that magic, and that's cool to see.

DEADLINE: Well, as a gay stoner who went to Harold and Kumar in theater in high school, I'm looking forward to the next movie.

Penn: Oh, thanks. Well, you're gay - I just wrapped this Greg Araki movie yesterday.

Deadline: I love Greg. You work with him on the decline of the damn western civilization? Great title, how did you get into the project?

PENN: So, I recently got signed to Anonymous Content and my manager basically called. Like, "There's a role in Greg Araki's new movie—" and I'd like to cut it, but I was like, "Okay, let's go ahead and make it happen." "Well," he says, "I'll send you the script, and here's all the details of the meetings and all that." It was one of those things, it almost sounds like a cliché, but I was like, "I mean, obviously I'm going to read it, but I can tell you right now that I'm going to follow this very hard." And part of the reason for that was because the first movie I saw when I moved to Los Angeles, I was an undergrad at UCLA, and it was literally the first week of theater and film school. There was a Doom Generation show on campus and Greg and the cast came to do a panel and a Q&A. And I didn't know anything about the movie, you just go in. And then listening to his Q&A about his kind of filmmaking and his guerilla-style shooting in Los Angeles and doing things the way he's always done things—which, obviously, I told him that story when I talked to him about this movie. But he says, “You know, I shoot in Los Angeles all the time. "I have never shot anywhere else." And he kind of walks you through things that I guess I knew as a Greg Araki fan, but it was really cool to hear. So, I was excited to join the cast, and I just packed up.