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Call Sheet: How ‘Grudge Match’ Director Got Stallone and De Niro to Say ‘Yes’

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See Sylvester Stallone, Robert De Niro and more talk "Grudge Match" with Yahoo Movies:

Making a movie ain't easy. And the level of difficulty is only amplified when you have two Oscar-winning cinema legends circling your project.

This was the case with director Peter Segal as he laced up for his boxing comedy "Grudge Match" (in theaters now). Segal eventually convinced Sylvester Stallone and Robert De Niro to join him in the ring (they discuss the project in the video above), but it wasn't always easy.

In our new feature Call Sheet — wherein we chat with talented men and women behind the camera about what it takes to get movie stars aligned on a film — Segal, a proven comedy maestro ("Tommy Boy," "Anger Management," "50 First Dates"), lets us in on his secret powers of persuasion.

[Related: ‘Grudge Match’ Surprise: Ireland Baldwin’s Acting Debut]

How did you get Mr. Sylvester Stallone to come on board?

Peter Segal: My first meeting was to try and convince him to do the movie, he was a little dubious at first because he had not done a lot of comedy and his last comedy was many many years ago. Bob [De Niro] was a little more used to tipping his hat to some of his earlier work with "Analyze This" winking at "The Godfather," and Sly had not done that yet so I met him at his office and the courtship began.

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'Grudge Match' director Peter Segal. (Photo by Dimitrios Kambouris/Getty Images)

What do you think tipped the scales in your favor?

P.S.: I had met with him about four or five times and then worked on the script and really tried to cater it to this character we were developing but then at the last minute when he was still hesitating Bob De Niro, made a call to him. I asked Bob if he wouldn't mind calling and talking to him from an actor's standpoint, actor to actor, how he felt it was so beneficial in his career to finally do a comedy and how it opened him up to a whole new kind of career with "Meet the Parents" and many other films. He agreed and called Sly and I think that's what put it over the top.

And what was your first meeting with Robert DeNiro like? How did he come aboard?

P.S.:Well what happened then, during this courtship period which had gone on for several months, even though Bob had initially agreed to do the movie, there were a lot of other movie roles lining up threatening to take our spot so I flew to New York to meet with him and had to convince him to stay and not to leave because we were so close to making the movie. The studio was not interested in making the movie without those two guys, like me, they felt that it was perfect casting and the only casting, so it was a precarious moment.

So what do you think convinced him? Your sales pitch? Passion for the project?

P.S.: I think it was that. I would not describe myself as a very good salesman, there are people who are much better bull-sh------ than me, I wear my heart on my sleeve and will very often accept rejection and just walk away but this time, I was not going to accept it. Even though Sly had basically rejected me a few times once we got him in I was not going to allow Bob to go off and take another movie, so I literally had lassos at both ends trying to tie these guys down because I believed in the project so much.

When did you have a moment of celebration, like "Hooray we're going to do this!"

P.S.: Funny you should ask that, my producing partner Michael Ewing and I will always toast to a green light and smoke a cigar in victory. For this one we did not toast, we did not smoke cigars, we did not believe that this movie was actually going to happen until we were on set, cameras ready to roll. It was too precarious, there were so many hurdles from budgets to deals to creative issues, so we never allowed ourselves to enjoy the victory of the green light and suddenly we found ourselves on set and it was almost a moment of disbelief. We kind of eased our way into the reality after the cloud of uncertainty.

[Photos: "Grudge Match" Premiere]

So which actor followed after Stallone and De Niro?

P.S.: It was definitely Alan [Arkin]and the hurdle there was his people didn't necessarily think he would be up for playing, as they said, "Another old guy role" and I thought to myself, "What are you talking about? He is an old guy, who is he going to play the young female in the movie?" But I gave him the script, because I had worked with him before on "Get Smart" and had a wonderful time, and he called me so positive and he just loved this role and kept going on and on about it and I was blown away, I didn't expect he'd have that reaction. He had about four notes and we did those in about five minutes and once we realized we had this amazing cast solidified, originally the role of Dante [played by Kevin Hart] was written for an older gentleman but I thought, now that this cast is coming together who would be best to throw in the ring against Alan Arkin as his adversary? So we thought why not inject a little youth into the cast so we went after Kevin Hart, who is one of the funniest guys out there. Him against one of the founding fathers of Second City could be a magical relationship and all of my dreams came true when those guys were on set together going at it.

When did Kim Basinger enter the picture?

P.S.: After those guys we focused on the role of Sally Rose and Kim kind of raised her hand and said, "Hey, I would love to be in a comedy and let my hair down." She hadn't worked in a few years and especially on something like this and I was thrilled she just wanted to play in the sandbox. I love it when dramatic actors just want to prove something to people, that they have a certain range. I was thrilled to have her come join us and she was a delight to work with.

When did you decide to add her daughter Ireland into the mix to play the young Sally?

P.S.: Well we went through a lot of technical procedures to de-age Bob and Sly, that was a nightmare it was so technical. But one thing we thought, we don't necessarily have to de-age Kim because her daughter Ireland looks so much like her, let's just use Ireland for the flashbacks. We couldn't find anyone who really looked like Bob and Sly enough, I really wanted to bring a reality to it, fulfill the promise of Rocky and Raging Bull but with Kim, Ireland was right there, the only difference is Ireland is about four inches taller than her mom so we just made sure we cast people around her who were the same size.

And finally Jon Bernthal, what made you think of him to play De Niro's son in the movie?

P.S.: Jon Bernthal, that was the role we spent the most time casting. It was a very tricky role and we weren't going after anyone who looked like Bob in particular, we were more going for their acting ability and someone who could play the lightness and bring the gravitas to it. One day one of our producers Bill Gerber was watching "The Walking Dead" and said, "My God that guy looks so much like De Niro it's not even funny." We brought him in and he had just finished shooting "The Wolf of Wall Street" with Scorsese and now he's opening up against himself, but I adore Jon and think he's a star on the rise and I can't wait to find another project to work on with him.

"Grudge Match" is now playing in theaters.

See the trailer for Peter Segal's "Grudge Match":

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