Director Peter Cheslom’s Serendipity was one of the first movies to premiere in New York following the catastrophic Sept. 11, 2001 attack on the city. On the one hand, the timing couldn’t have been worse, but for a soul-scarred nation, the timing couldn’t have been better. What the world needed then more than anything was love, sweet love, and Serendipity delivers. Two decades later, Serendipity is ranked among the best romantic comedies. Britain’s The Independent called it “sweet, cozy and completely irresistible… a rare Christmas movie/romantic comedy twofer.” It also affectionately called it “completely bonkers.”  Serendipity stars Kate Beckinsale as Sara, a woman who fervently believes in fate and destiny, and John Cusack as Jonathan, who comes round to that opinion following an idyllic platonic night they spend together after meeting by chance in a department store. Three years later, each, while engaged to others, cannot shake their seeming soulmatedness and takes steps to fulfill their romantic destiny. Serendipity, a Paramount Home Entertainment release, is available from Redbox to rent or own on demand. On the occasion of its 20th anniversary, Cheslom spoke with Redbox about how directing a rom-com is like hosting a cocktail party, giving absurd notes to comic genius Eugene Levy and why it was necessary to withhold Sara and Jonathan’s first kiss until the end of the film.

Redbox: Was it a fortunate accident that you got to direct Serendipity?
Peter Cheslom: I’ll be honest with you, I knew that my career was about to end because of Town and Country (an all-star screwball sex comedy fronted by Warren Beatty that despite some good reviews flopped at the box office) and I did it knowing I had to get back on the horse. I didn’t want to work for Miramax again and I read the script not wanting to like it, but it touched me. It was a fortunate accident because I didn’t take it seriously at first, but I was in the mood to be playful after what I’d been through (with Town and Country).

RB: What were your impressions of rom-coms in general?
PC: I like the balance (between the romance and comedy) in Serendipity. I think it’s why it hasn’t dated as much as other rom-coms of the early 2000s, many of which I think are sexist. I watched it again yesterday and I what I love about it is it’s equally her story as much as his.  It is the most improbable stuff; I sat watching it thinking, ‘I don’t believe it,’ and then you go, ‘Okay, you got me, I’m on board.’ It’s seductive and it’s about a world we hope exists. I was laughing to myself because at the end when they reunite on in the ice rink, the soundtrack goes to this beautiful silence. There is a wind in the tops of the trees and a distant sound of English village church bells. Neither of which exists in New York. I pray to the magical non-reality and that’s what I still think works.

Making a movie like this is like being the host of a cocktail party. You have to keep it fizzing and keep everyone up: ‘Is everybody okay? Have you tried the canapes?’ But it’s what you have to do.

RB: Your cocktail party has stellar guests. What was it about Kate Beckinsale and John Cusack that made you think they would click so indelibly?
PC: Kate auditioned with an American accent, and I suggested she play it in her native British accent. I think this is one of the warmest most relatable performances she’s given. She’s a really good actor. When at the end she bursts into (Jonathan’s) wedding and has to pretend it’s terrible that it has been called off while being filled with glee, that touched me. And John I’ve known for a long time. We had been looking to work together. He grounds the film because he’s endlessly pointing to the ridiculousness of (the situation). You get on the train with him.

RB: I’ve read that Jennifer Aniston was considered for Sara.
PC: I was doing reshoots on Town and Country and she came to visit us. She was in my trailer and I remember her saying, ‘The thing is, I do a romantic comedy every week on ‘Friends.’ So yeah, I’m sure if she wanted to do it, it would have been offered to her. But that was her saying she didn’t think it was right for her. But it’s impossible for me to imagine anyone other than Kate in the role. I know all directors say that about their movies, but it’s very true.

RB: Another couple with great chemistry in the movie is John Cusack and Jeremy Piven (as Jonathan’s best friend). They are both Chicagoans and longtime friends.
PC: Their history and chemistry were invaluable. I loved their energy together.

RB: You’ve directed two of my comedy heroes, Jerry Lewis in Funny Bones and Eugene Levy in Serendipity. What was it like to work with him?
PC:  When (in the department store) he sells John’s character the purple suit and discloses that he doesn’t have the information he wants, Eugene said to me, ‘What do I do now?’ I said for him to go back to his kingdom behind the counter. When he asked how he should do that, I said to tap Jonathan on the shoulder and say, ‘Chase me.’ The other note I gave him was for the scene in the credit card archives. I told him to pretend he was James Bond for one second for no reason other than his life is so unexciting, and this would be the best evening he’s ever had. To be able to give someone like Eugene Levy such absurd notes and for him to (believably) ground them was absolute bliss.

RB: This is Serendipity’s 20th anniversary, which of course coincides with the terrible events of 9-11. There were reports that (producer) Harvey Weinstein demanded the digital removal from the film of the Twin Towers. Is that something you regret now?
PC: Definitely, but that’s very easy to say in hindsight. We were the first to premiere a movie in New York after 9-11. There was a lot of trepidation about the premiere, but it turned out to be an incredible evening. It was almost like we could live and laugh again. I think Harvey was being very sensitive, but that was a decision that he had to make.

RB: I also understand there was a version where Sara and Jonathan kissed early in the film.
PC: Yes, I took it out. (By the end of the movie) you should be aching for them to kiss, and that ache would have gone away. Everyone wanted to believe that there is that one person out there and that that one kiss would verify that. We also reshot the scene inside the café. I needed Sara to explain why serendipity is one of her favorite words, and to define it as a fortunate accident. I needed that so the audience would relax and say, “Aha, I see what world we’re in.’

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