Exclusive: How Jimmy Kimmel Live Pulled Off Its Matt Damon Episode

Viewers of Jimmy Kimmel Live tuned in Thursday night to see the late-night host bound and gagged at the corner of the stage. Matt Damon had hijacked the show, and proceeded to oversee what may have been one of the most star-studded episodes in talk show history.

The Damon episode, of course, was the culmination of a long-running joke by host Jimmy Kimmel. For a good chunk of Jimmy Kimmel Live's ten-year run, Kimmel had ended each episode by apologizing to Damon for bumping him from the show. Now it was time for Damon's revenge.

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Damon even brought in Sheryl Crow to replace Kimmel's bandleader, Cleto Escobedo, while actor Andy Garcia took over the sidekick role normally handled by Guillermo Rodriguez. Robin Williams helped Damon deliver his monologue; Ben Affleck was (briefly) cue card man, and Nicole Kidman, Reese Witherspoon, Demi Moore, Amy Adams and Gary Oldman shared an extremely tight couch.

In reality, of course, the Damon episode was the product of four years of heavy planning by Kimmel and his production team. Executive producer Jill Leiderman spoke with TV Guide Magazine about turning Damon into a talk show host, attracting so many A-list stars and even bringing Kimmel's ex Sarah Silverman back to the show.

TV Guide Magazine: When did you start plotting this episode out, and how did you get Matt Damon to get on board?
Leiderman: The relationship with Matt has been cultivated ever since the "I'm F***ing Matt Damon" video. As you know, Jimmy mentioned Matt and "bumped" him for the first time in 2005. So the relationship has been percolating, and we've been working with Matt and his publicist, Jen Allen, for all of these years constantly coming up with new and creative ideas and ways in which we can grow the relationship. Jimmy and Matt have become closer as well over the years.

TV Guide Magazine: How did the long-running apology-to-Damon gag come about in the first place?
Leiderman:  In order to make our co-executive producer Jason Schrift laugh, Jimmy mentioned Matt as somebody who was still waiting in the green room to come on one night when our guest list wasn't all that illustrious. So what we continue to try and do is find creative ways to inject Matt into our show.

TV Guide Magazine: How long have you been hoping to do this episode, the culmination of that joke?
Leiderman: This was an idea that came about four years ago, and we've just been waiting for the right time. From the moment we discussed it, we always knew he would host the entire show but we didn't want it to get out there early because we wanted the surprise for our audience, that when they tuned in Matt had hijacked the show. It seemed like the right organic way to really once and for all put a fine point on the relationship, and have this epic archrival relationship come to a head. So for the past four years we've been trying to figure out with Matt's schedule when the right time would be.

We wanted the time to shoot field pieces with him, brief him, give him the experience to prep him to be able to drive his own late night show. The entire production team came together and rallied behind both Jimmy and Matt to create all the content that we put on the show last night.

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TV Guide Magazine: How much time did Matt have to prepare?
Leiderman: The day before the show, Matt came in and gave us a full day of walking through the set, experiencing what it would be like to drive his own show and doing field pieces. Much the same way Oprah did when she gave us a full day as well for our Oscar special last year. He threw himself into the operation and wanted to soak up everything that we did and was game for anything we wanted to do. It was 48 hours of crunch time when it became a circus, but a very exciting circus.

TV Guide Magazine: Did he do a test show? Did you give him talk show pointers?
Leiderman: He did a dry run at our rehearsal and did jokes for the staff and crew to see what played well and what didn't. And Matt himself read up on all the research we gave him on each guest so that he would be well versed and be able to throw his own material in. What you saw on the show was an amalgam of Jimmy's ideas, the writers' ideas and Matt's input as well.

The best thing is, like Jimmy does every night, Matt had 209 people at his disposal to help him experience a one-night-only event. It was refreshing for us, to have the opportunity to work with somebody who has never done it before and show him the kind of machine that we have built here.

TV Guide Magazine: For someone who had never hosted a talk show before, how do you think Matt did?
Leiderman: I thought he was great. Moments before he went on, I looked at him and said, "OK, now's the time when you get to go and enjoy yourself. Go out there and have a great time."

TV Guide Magazine: Talk about the guests. How did you manage to attract so many A-listers at the same time?
Leiderman: Our talent bookers worked around the clock. Matt himself chipped in and called friends. There were friends of Jimmy's on the show, friends of Matt's, friends that they have in common, as well as other celebrity guests that we brought in as well to really prove that when Matt hosted the show we were able to blow the roof off the dump.

TV Guide Magazine: Where did the idea come from to have Sheryl Crow, Andy Garcia and Robin Williams take on key aspects of the show?
Leiderman: Jimmy and our writers thought the concept of upgrading our show and the players on our show with A-list talent would be a great idea. We reached out to Sheryl Crow to participate because she had done work with Matt's charity, Water, in the past. So we knew there would be a great connection there.

I just got off the phone with Robin Williams' manager, who wanted me to know that the experience was "spectacular." We knew we wanted to bring in a ringer at the end of Matt's monologue and wanted it to be someone who's organically woven into Matt's life. The idea that Matt himself could pull in a world-class comedian to finish off his monologue is really exciting. As soon as we asked Robin he gave us a "yes" almost immediately. And he changed around his whole travel plans to be with us.

TV Guide Magazine: Did Jimmy enjoy getting lap dances, as he was tied up, from Robin Williams and Nicole Kidman?
Leiderman: The Robin Williams lap dance went on for about two minutes longer. And he was very proud of it. We have the footage. We're going to save it for the Christmas highlight reel.

TV Guide Magazine: It sounds like you had to cut some things down.
Leiderman: We had a ton of extra material that unfortunately had to be cut out. We were ten and a half minutes long. We had to unfortunately make decisions on what got pulled. More of everything, basically. (Friday night) on the show you'll see a bit on the show that was originally supposed to run but didn't. It's a field piece featuring Matt going around with a camera crew to meet Jimmy Kimmel Live's neighbors and find out how Jimmy has treated them.

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TV Guide Magazine: It looked like Andy Garcia took his role as Guillermo's replacement very seriously.
Leiderman: Andy Garcia was very excited. He is so funny and he was also very excited to play ball with us. He was very method about his experience. He wanted to stay true to Guillermo's character as much as possible. So he had Guillermo speak and get him to line read to make sure that he represented him as closely as possible.

TV Guide Magazine: This was the first time Sarah Silverman appeared on the show since she and Jimmy broke up. How did that happen?
Leiderman: I can't speak to Jimmy's personal life but I can say that they're both incredible professionals and they're both great human beings. They came together for this show and for Matt. Sarah wanted to show support for both men. It was great that she was game to come be with us. She's got a great heart.

TV Guide Magazine: Having just moved to 11:35, this felt like you guys were looking to make a big statement, that you've come to compete.
Leiderman: We learned the comedic sensibility that has shaped the majority of our show through David Letterman. And our work ethic and what we generate is very indicative of the kind of work that he has done. Coming into this daypart and going against these two guys, it's an injection of energy that has shown up in this arena that heretofore didn't exist at 11:35. Formerly it was those two gentlemen going head-to-head for such a long time. It's just exciting for us to get the shot to come in and show everybody what we do.

TV Guide Magazine: ABC is going to re-air the episode in primetime, next Tuesday at 10/9c.
Leiderman: I guess we did a good job! I don't think we have much time to sit on our laurels though. We've got the big post-Oscar show coming up at the end of February. So we have a big celebrity comedy piece that we've got to book.

TV Guide Magazine: And now the expectations are high. How do you top last year's "Movie: The Movie"?
Leiderman: Well, that's a very, very good question.

TV Guide Magazine: Is there a new celebrity that Jimmy will bump every night? Is the Matt Damon gag over?
Leiderman: What's the expression? "Old habits die hard"? I don't think he's going to be able to break himself from the habit of bumping Matt Damon. We'll see if Matt shows up again today, and we'll see if we have time for him.

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