Brett Goldstein got so famous for his Emmy-winning role as Roy Kent on Ted Lasso that most people have no idea he has been a professional stand-up comedian for nearly 20 years.
Now, that is all about to change when he debuts his first-ever stand-up special, The Second Best Night of Your Life, on HBO this Saturday night, April 26.
In this episode of The Last Laugh podcast, Goldstein talks about why he resisted putting his live show on tape for so long, how fans of his TV work are often surprised by the real him, and how his comedy serves as a much-needed counterweight to the toxic “manosphere” trend. He also discusses his accidental acting career in both Ted Lasso and Shrinking, why he’s just as surprised as everyone else that he’s returning as Roy Kent, and addresses the swirling rumors that he is dating his upcoming rom-com co-star Jennifer Lopez.
Before Goldstein’s new special arrives on HBO this coming weekend, it has been nearly impossible to even find video clips of him performing live online. He’s never done stand-up on late-night TV and has generally avoided filming his act in any way. “I just like it live,” he says.
“I really believe in the room with the audience, that’s where you feel it. That’s where you try stuff. The game of it and the fun of it is this sort of energy that happens live. And it’s really hard to capture that.”
But after touring this new hour for more than a year, he thought to himself, “I guess it is nice to memorialize it in some way, to have some record of it that you can show your grandkids that I’ll never have.”
Early in the special, Goldstein acknowledges that the glamorous Hollywood life he leads now is hardly relatable to the average comedy fan. He tells stories about visiting Joe Biden’s White House with the Ted Lasso cast and guest-starring on Sesame Street alongside Cookie Monster. He also makes a point to separate himself from his more aggressively masculine character of Roy Kent, joking that being a man post-#MeToo is like being a German after World War II.
And while that point of view stands in sharp contrast to the hyper-masculine comedy that has become even more popular during the second Trump term, Goldstein insists he’s not actively trying to counteract those toxic sentiments.
“It is just what I think, and it’s truthful to how I feel as a man,” he says. “The beauty of stand up is every time you’re trying something, you’re kind of saying, ‘Is this normal? Is this mad? Am I insane?’ And if they laugh, it means no, I think that, too. Or you are insane, but it’s funny.”
Below is an edited excerpt from our conversation. You can listen to the whole thing by following The Last Laugh on Apple Podcasts, Spotify, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Wednesday.
I’m sure you have a lot of fans who only know you from Ted Lasso. And the character who you play on this show, Roy Kent, is very different from the real you. Do you ever feel like people are expecting that guy when they come to see you?
I have no idea what people were expecting when I went on tour. Because I know that 99 percent of them hadn’t seen me do stand-up, probably only knew me as Roy Kent, so I have no idea what they were expecting. I thought I was going to have to address it. What I really, really didn’t want to do, but was prepared to do if I had to, was be like, “Hey, you all know me as Roy Kent, but I’m more like this.” I didn’t want to do that. I would rather just present this thing. And to be honest, I was surprised and delighted that I never had to do that. I really didn’t have that problem. And I suspect the reality was their expectations were probably very low. Because they probably thought, “Oh, this is an actor trying stand-up!” And they didn’t know that I actually have done stand-up for a very long time.
You do talk on stage about how Ted Lasso changed your life and career in this major way. You kind of became an actor in that way by accident, right?
Well, halfway through writing it, I was like, I think I’m Roy Kent. And I wrote an email when we finished writing it to [co-creator] Bill Lawrence, and I said, I think I could do this, but I understand no one’s thinking of me for it, and this might be really embarrassing. And I made a self tape, and I sent it. And I said, if this is good, great, and if it isn’t, let’s never speak of it again. I will never ask you. And then he sent me an email, saying, this is awesome, let’s do that.
I’m sure you were pleased that he liked it and wanted to cast you in the role. But was there a moment where you realized, oh, now I now actually have to do this? And was that scary at all?
Yeah, it was all scary. It’s always scary when you get a job. You’re very excited about a thing. You work really hard to get the thing. Then you get the thing, and you immediately think, oh god, what have I done? And Ted Lasso is a real extraordinary one in that we genuinely had no idea how it would go. I did not think anyone would watch it. I knew everyone else was brilliant, I knew it was special, it felt magical, but I wasn’t sure if I was any good. I’ve done so much stuff that no one saw, and I just thought this was going to be another one, so the whole thing was kind of magic.
How do you explain the massive success that it was? There was a lot of talk at the time about how the uplift of it matched the moment of the pandemic, and that people needed something like that in their lives. How much do you think that played into it?
I can only guess, because I think these things are kind of magic, but I do think that a big part of it was that it was a refreshing change from everything we were seeing. And what we were seeing was so much negativity. So many of our public figures were openly rude and horrible to each other, and hostile and sowing division, and all of that stuff. And here was this American, who is ignorant, who doesn’t know football, but who is coming into a world with an open heart and with curiosity, and not being judgmental, and trying to make things better by bringing people together. And as cheesy as that sounds, I think there was nothing going on like that at the time.
When it came time to make Shrinking, your next show after Ted Lasso, you did not write yourself into the show at first, but then, of course, you did take on a major role in Season 2 playing an even more challenging dark character, with less comedy to it. What was it like to take that on, because I think again there was a little bit of reluctance on your part?
Well, that one was Jason Segel’s idea. We were casting that part, and he brought me and Bill Lawrence to him, and he said, “Why isn’t Brett doing this?” And Bill was like, “I don’t think so.” And I was like, “I don’t know.” But Jason was like, “Think about it, I’m serious, he’s the right person for this.” And then that night, we both thought about it, and in the morning Bill called me, and he said, “Look, I believe you are an artist, and I believe in you as an artist, and I will support you 100 percent. And if you think you can do this, you should do this. But if you f--- this up, the entire season rests on this character and you’ll ruin everything, bye!” And so, there was a lot of pressure on it. But do you know what helped me? In between seasons, I did this film, All of You, with Imogen Poots that comes out later this year. I co-wrote that film. And it’s kind of meant to be as natural as possible. And it’s funny, but it’s funny in the way real people are funny. It’s kind of stripped down, really vulnerable, and having a safe space to be that f---ing vulnerable helped when I went to Shrinking. Because that part is like an open wound.
And now, of course, you’re going to go back to do more Roy Kent in a fourth season of Ted Lasso, which, I don’t think you thought was ever going to happen.
Did not think that was going to happen.
Were you surprised that that is happening, and that you’re going to be part of it?
Honestly, I don’t quite know. I think half and half. When it finished, it seemed unbelievable, but then we did all cry like it was real. I’m sure a part of me was like, I hope this isn’t it. And I’m sure it isn’t.
Yeah, it does kind of seem like nothing ever dies anymore. Shows don’t end in the way they used to.
It’s a lovely world, isn’t it, the world of Ted Lasso? It’s such a lovely world to be in. It was just sort of sad to close the door on it.
So you mentioned one of the upcoming films that you wrote. The other one, Office Romance, which I believe you’re shooting now, stars you and Jennifer Lopez. What can you share about that one?
All I can tell you is, I wrote it with Joe Kelly, one of the co-creators of Ted Lasso, and a f---ing brilliant writer. It is an old school rom-com in the Nora Ephron, Broadcast News way, but with hard R jokes.
And the idea of casting yourself opposite J.Lo, was that an easy decision?
We wanted to do an old school rom-com, and we were like, who’s the best rom-com actor who hasn’t done it in a while? And it was like, J.Lo! And I have to say, she’s f---ing brilliant. She’s so funny. She’s just a perfect rom-com actor. She’s just so good at it. And when you see it live, you’re like, oh, wow, it’s a real quality that’s very rare. It’s infinitely charming.
Because of how famous she is, the rumors that the two of you are dating have already started. I don’t know if you’re aware of that.
I have had people from school ask me, yeah.
How do you deal with that stuff? Now that you are gaining more fame yourself, and then being close to these very famous people, it must be just a very odd experience.
It’s very odd. And I try not to look at any of it or see any of it, even though f---ing people will send you stuff, because if you engage with it I’ll lose my mind. It makes me very anxious. I’m a very private person, and I like to be able to go to Target.
Is that getting harder?
Slightly. But I’m doing the thing that I always dreamed of doing. So I’m very, very lucky. But yes, that stuff will give me a nervous breakdown if I really think about it.
But your friends are calling you to ask if it’s true?
Yeah… yeah. It’s insane.
What did you think that your professional life would be like compared to how it is now?
I didn’t think any of this would happen. Listen, Ted Lasso didn’t happen until I was like 38 or something. I’d been around. I’d been making stuff and doing stuff for nearly 20 years without huge success. I always made enough money to pay my rent and go to the cinema and I was OK with that. I just was happy to be doing stuff. I sort of really mean it when I say that going on Sesame Street was so the pinnacle that if I die now, it’s fine. I really, really mean that. I have done so much more than I ever believed was possible, and I feel incredibly lucky, and I love that I get to do it. And who knows how long that window is open? So I’ll make the most of it. But if I get run over today, what a great time.
Listen to the episode now and follow The Last Laugh on Apple Podcasts, Spotify, or wherever you get your podcasts to be the first to hear new episodes when they are released every Wednesday.
