Almost exactly 30 years ago, two young aspiring actors named Grant and George signed up for an acting class. They immediately got along and as well as sharing opinions on such important, friendship-forming subjects as sports, women and humour, they both had an optimism that they would, some day, somehow, make it.
"You can probably see our old acting school from this window!" grins Grant Heslov, gesturing towards the giant window in the Beverley Hills hotel suite where he has spent the day doing interviews about his latest film, The Monuments Men. Just across the hall, George Clooney is doing the same. Upstairs, the stars of the film that Heslov and Clooney produced and wrote together (Clooney also directed and stars), including Matt Damon, Bill Murray and John Goodman, are doing likewise. They are only six blocks from their old school but it feels, Heslov agrees, a long way away.
In the intervening decades, Heslov and Clooney – who, you'll be delighted to learn, did eventually make some headway as an actor – started up a film production company, Smokehouse Productions, named after their favourite LA hangout, which has made some of the more interesting little films of the past decade. Heslov has been nominated for an Academy Award four times – twice for original screenplay, for Good Night and Good Luck and The Ides of March – and won the big one last year when Argo, which Smokehouse produced, took best film. Heslov, who looks like John Turturro's sweeter and slightly goofier brother, seemed calm to the point of blasé when he got up on stage that night (especially next to a near-hysterical Ben Affleck), collecting his award from Jack Nicholson, after his win was read out by Michelle Obama. But in truth, he says, he was near a state of shock.
"God, that was awesome," says Heslov, plucking at his jeans as if still pinching himself. "Honestly, it's one of the great, great experiences, to do that. Yeah, I've got that monkey off my back now."The Monuments Men: (l to r) Sam Epstein, George Clooney, John Goodman, Bob Balaban and Matt Damon in the second world war film co-produced and co-written by Heslov and Clooney. Photograph: Claudette Barius
Heslov has been so successful as a producer and writer, winning 18 awards in less than a decade, that he confesses to feeling a little disappointed with the reception for August: Osage County, which Smokehouse also produced, even though on the morning we meet it was announced that this film was nominated for two major Oscars: best supporting actress for Julia Roberts and best actress for Meryl Streep.
"Oh yeah, those guys are great," he replies when reminded, with an equanimity that belies his ambition.
Heslov couldn't be further from the usual image of a high-powered movie producer if he walked around in a clown suit. He is soft-spoken and far happier asking questions than answering. Whereas Harvey Weinstein barrels around the world like a bull looking for a fight, Heslov radiates the gentle contentment of a pony quietly munching apples in a sunny field.
Heslov directed and produced the film version of Jon Ronson's book, The Men Who Stare at Goats and Ronson testifies to his and Clooney's unusual generosity: "During the release of the film, [Clooney and Heslov] were very welcoming and unassuming and inclusive." (Heslov returns the compliment, in a way: "I love Jon – he writes some crazy shit. He's just a nut and I love him.) "I think Grant and George are very close-knit," Ronson says. "My theory is that life in Hollywood makes you rightly suspicious of other people's motives. It's a very alpha-male business. So when people find other people they trust they form a close bond."
Heslov mentions Clooney frequently and warmly, and their likemindedness about what will make an interesting story is a testament to their friendship: "We have eclectic taste, but we always just know what will work for us," he says. Sometimes they choose stories as a reaction to current events: 2011's The Ides of March was a response to America's fervid political climate; 2006's Good Night and Good Luck was "a reaction to what was going on with the war, and George speaking out about the war and getting hammered," Heslov says.
They write their scripts together, sometimes alternating scenes, sometimes line by line, with Heslov on the computer and Clooney handwriting. "I find writing really difficult – definitely the most difficult of all the things I do. It's like pulling teeth for me, so it's great to have George there to crack the whip." (For his part, Clooney has dryly said that he's grateful to have Heslov around because "he's a magnet for all the paparazzi – he soaks it up".) Was it strange when his close friend started to become so insanely famous? "Oh sure, but you get used to it, and George takes it in his stride. He gets a lot of criticism, too – people online can be so brutal!" he says, his eyes wide with shock at the cruelty of the internet.Ben Affleck in Argo, which won the best picture Oscar for producer Grant Heslov. Photograph: Courtesy Warner Bros
The Monuments Men is not, to be honest, one of their best films, but it's easy to see what attracted them to the story. Based on Robert Edsel's book, The Monuments Men: Allied Heroes, the film focuses on the ragtag group of Americans, played by Clooney, Damon, Murray, Goodman and Bob Balaban, one Brit (Hugh Bonneville – Heslov is a big fan of Downton Abbey) and one Frenchman (Jean Dujardin, who is sweet in the film, even if he clearly only understood about one English word in every five of his lines) who were formed to try to save some of the great works of European art and architecture from being destroyed and pillaged during the second world war. The men tear through Europe, aided by Cate Blanchett with an 'Allo 'Allo French accent. It's a great story but it's hard to get too emotionally involved with the art when the film keeps showing piles of furniture stolen from deported Jews and dying soldiers on the sides of the road. Steven Spielberg, in the first and third Indiana Jones, got around the problem of telling a second-world-war story that has nothing to do with the victims by simply not mentioning the victims at all, making it easier to care about Indy's pursuit of religious artefacts. Clooney and Heslov, by contrast, make heavy weather of the issue by having Clooney's character, Frank Stokes, give repeated speeches about how saving the art is analogous to rescuing western civilisation from Hitler. Which it is, to an extent, but it's not always easy to remember that when you see another shot of a barrel filled with Jews' gold teeth.
Were he and Clooney anxious that audiences might feel there are more urgent stories to tell about the second world war other than the art?
"Um, you know, we weren't worried, but I know there will be people who say that," he says. "So we made a conscious choice to make it about the culture as opposed to a single piece of art to show the importance of what these guys are doing."
Heslov, who grew up in LA, was raised conservative Jewish – "but on the liberal side of conservative" – by his father, a dentist, and mother, a businesswoman. Given his background, had he wanted to write a film about the second world war for some time?
"It wasn't something I'd been consciously looking to address, but part of what I loved about making this film was being Jewish and being able to tell this story that affected Jews all through Europe," he replies.
Clooney and Heslov never imagined they would end up writing, producing and directing films together when they met as struggling actors in the 80s. "And, in fact," Heslov says, with some satisfaction, "I was more successful as an actor than George back then, having had some TV spots."Grant Heslov with Affleck and Clooney at the 2013 Oscars Photograph: Kevin Winter/Getty Images
Heslov had always wanted to be an actor. But once he started making appearances in films such as True Lies and Dante's Peak, he realised there was "all this other stuff, like producing and writing, that you don't see when you're just a kid watching movies. And I thought, 'I think I can do this.'" He attributes his success since to "hard work, luck and a bit of talent – but you don't know if you've got the talent or luck until you put in the hard work."
Familiar faces reappear throughout his and Clooney's films, such as Damon (who was in the Oceans films that Clooney produced under his previous production group Section Eight) and Goodman (who was in Argo). Murray has already said that he'll come back for anything Clooney and Heslov make. Is there something in particular that they look for in an actor?
"There's a certain amount of 'what's going to make our lives easiest?' George and I are both doing so many things on a film so we want guys – and gals – who are going to be fun to work with and aren't going to be a pain in the ass."
So is writing and producing films with George Clooney and winning Oscars as fun as it looks?
"Fun? Is it fun?" he asks, looking downright perplexed at the question. "Well, it's hard but, I love it and, well, yeah. Yeah, it's pretty fun."
• The Monuments Men is released on 14 February
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