Interview: Casey Patterson On Producing ‘The Greatest Roast Of All Time: Tom Brady’

Casey Patterson is no stranger to  producing television specials. For the last 25 years, she has produced and overseen various specials and awards shows including Lip Sync Battle, Spike TV’s The Scream Awards, the MTV Movie & TV Awards, The TV Land Awards, A Very Murray Christmas, The Concert for New York City, The Concert of the Century at the White House, and The Diamond Jubilee of Elizabeth II at Buckingham Palace. 

Most recently, she produced Netflix’s The Greatest Roast Of All Time: Tom Brady, which earned an Emmy nomination for Outstanding Variety Special (Live). We spoke with Patterson about producing the groundbreaking special. 

Congratulations on the well deserved Emmy nomination. 

Thank you so much. 

Your experience producing specials is beyond extensive. Can you just talk about how you got involved with the roast? 

Yes, Tom Brady and I share agents, and we’ve been talking about trying to do something together for years. Also, Jeff Ross and I are friends and have done a lot over the years in the comedy space. I believe what he told me is was that he hit Tom up after the Super Bowl on Instagram and said, “Hey man you should do this,” and so we all sort of just jumped in together.

The roast was part of the Netflix is a Joke Comedy Festival. Was the timing of that intentional? How did how did Netflix get involved?

What’s interesting is that it immediately sold to Netflix. It was right when Tom was retiring the first time and we’re going do it right after he retired. We were set up we and were ready to go. It was live to tape, as roasts historically are for good reason, and then when Tom unretired and played again. It just so happened that the timing could potentially sync up to be around Netflix is a Joke which is the most amazing cultural comedic festival. So, we were thrilled that the timing worked out. It really came down to Tom and his appetite for doing something like this live. He’s a brave soul. 

Was was there any hesitation to do it live? There are so many things that can go wrong with something like this.

From a broadcast point of view, absolutely not. A roast had never been done live, and a roast of this kind typically isn’t done live because that’s only because the best version of roast comedy involves people who are non-pros. You have comedians who are used to doing live tight sets, but you always want people who are civilians who are just a part of that person’s life to come out, and that’s really difficult timing wise. It is an art,  and we’ve always wanted to have those kinds of people on these dais. I think it’s always been historically safer to do it that way. So, it was important that we thread a little This Is your Life under Tom’s story. It’s such an extraordinary story. I always talk about live being or this kind of comedy being the dais needing to be people who’ve earned the right to tell the joke. It’s such hard to do. I think it’s best coming from, “I love you man you’re my brother. You’re my teammate.” They can have good fun with him up. We roast the ones we love. So, the only nerves we had about going live was really just the amount of people. If we’re telling the story of Tom’s career and life, it meant that we would have a lot of people who are not comedians. 

I would imagine a concern is that you’re gonna be airing something that’s it’s not gonna land with the audience. 

For people who aren’t professional comedians, it’s hard to get them to do a very tight set that you can land on a dime. It’s really tough. The majority of the dais are non pros, so I think it was that, and then also just big risk is that the content is rough. I think so great for the audience is the nature of this is, in any stand-up, when you get a laugh, you’re emboldened and you keep going. I think Gronk is the best example of that.

Or someone like Drew Bledsoe,  who absolutely crushed. He had the timing of of a comedian. 

Crushed. How amazing was Drew Bledsoe? When we asked him, I don’t think we got the full sentence out before he said ‘yes.’

Yeah, that might have been brewing for a little.

He wrote so much himself. Those guys had the time of their lives. Julian Edelman took his material to comedy clubs. They all had a great camaraderie. They wouldn’t tell each their jokes. And Tom was fully onboard. He knew he was going to have to take the hits. 

The special had a pretty long tail on social media, thanks a lot to Nikki’s set, which blew the place down.

Nikki, Gronk, Edelman, and especially Belichick. There was so much momentum thanks to Bill Belichick. 

I was gonna ask you about that. There has been so much reported bad blood between Tom and Belichick after Tom left. What was the process of getting Bill Belichick on board?

He was last booking. We had been talking since the beginning, but he was the last to book. 

Again, I think what makes a good roast is it’s coming from the people that know you best. I have such a tremendous amount of respect for the audience, and I can’t try and sell a different lineup to you as the most important people in Tom’s life. These are the people that were there to bear witness to his career good bad and ugly, so it was really important to us that he be there. Bill Belichick never said no, bur he was cautious. I’ve been doing this very a very long time. There’s a tipping point with these events, where you have just enough bookings of the right people, where the people holding out go, “All right they’re gonna do that right.” We really had to earn. Are you gonna do this right? Is it just gonna be comics who don’t know him, or is it really gonna be his team? Are we all in this together? 

For as many fans that Tom Brady has, there are lot of people out there that don’t care for him. Was that a concern for you, or was that what you were banking on? 

I loved it. That’s the beauty of the roast. If you’re a fan of Brady, you’re in. If you hate Tom Brady, you’re in twice. That’s the great thing about a roast. It’s a sporting event. You’re going to get the highlights. You’re going to get the people who were there. You’re gonna get the reunion of the dynasty. But you’re going to get the honesty of it all. 

Can you talk collaborating with Jeff Ross? 

I have known Jeff for 25 years. I would put Jeff on every show that I did in one way or another, whether it was Rock the Troops with Dwayne Johnson in Hawaii or Lip-Sync Battle or the Movie Awards . We would always have Jeff on. I love him in every capacity. I have so much respect for Jeff because he lives and breathes in this world. I got a call once from Don Rickles, who said “I’d really like a roast of me, and I would love for you to do it. I know you’ll handle it sensibly.”  So, I was lucky enough to be able to do that, and I can just say nobody carries that torch and that mantle forward in the way that Jeff does. He really is such a good shepherd for that style of comedy and he really is coming from a place of, “Yeah, we’re gonna hit you hard. This is gonna be real comedy but we do it out of love.” Rickles was so great that everyone thought he was he was such a mean guy, but he was actually so sweet. He was a matador. Jeff is spectacular, and he has such tremendous knowledge of the audience, and what will work and won’t work. He’s so beneficial to have behind the scenes. But it’s a competitive sport, so there comes a time where you have to separate yourself with the other roasters, and Jeff now occupies that chair. I loved the way that he came out. It was so brave. That’s all Jeff right unbelievably brave, So, yeah he’s spectacular. 

Whose idea was to bring in Kevin Hart the host?

I think that was a conversation with Netflix. They’re in business with Kevin on a number of levels and I think when they talked to Kevin about doing a roast for Tom, he didn’t hesitate. I’ve worked with Kevin for years. He’s a spectacular partner and I think Kevin raised his hand so fast because people were so ready to have a big night where it was OK to cut loose. I think he was drawn to the moment. We were a little concerned about the arena. You’re telling a very personal joke to someone who’s sitting three feet from you, but we were in an arena and we were live. So, how do you marry those two things? Arena comedy is up and out, and roast comedy is direct hit. There’s just nobody better than Kevin to understand how to bring people around and make it feel intimate in such a big setting. He was masterful.

It looked like the production went on without any real hiccups,  but was there anything that maybe didn’t go as planned? 

We were supposed to be two hours. 

Wow, well I imagine going long is going to happen in a live event on a streaming service which has no time limitations, but that’s an extensively long longer than two hours. 

I was shivering under the truck. It was a decision. Staying on time is in our DNA, so there comes a moment in the truck early on when you know you’re spreading. We had the ability to talk to Kevin, though we actually never did, but we could have spoken to Kevin and said, “Hey pull it back.” I think 40 minutes in we knew it was going long, so we reached out to Netflix, and I have to give them credit for taking such a big swing doing such a capstone event live, and said,  “Do you want us to pull it back?” Which meant everything would get tightened in real time, but they said, “No, the audience is with us. Let it fly.”  Every once in a while you get lightening in a bottle, and I think everyone could feel that that’s what was happening and they were just brave enough to say, “Go.” So, we never had to speak to Kevin. Anything that long is a Scorsese movie, and  poor Tom had to sit through that for three hours and deliver a rebuttal. But he Tom Brady’ed it. 

The Greatest Roast Of All Time: Tom Brady is currently streaming on Netflix.