Sam Mendes: Triumphs that cannot soothe a troubled soul

With a new film to add to his formidable list of credits - not to mention a dazzling girlfriend - the star director ought to be happy. If only it were as simple as that

Only one man in Britain can be featured both on the front page of Heat magazine and in academic discussions on BBC2's Late Review. Only one man will this week be the focus of attention in the most low-brow of multiplexes and the most highbrow of London theatres. Yet, given that he is one of the most famous men in Britain, we know surprisingly little about the director Sam Mendes. Can a genuinely nice, 37-year-old bloke from Reading emerge unscathed from the vipers' nests of London's West End and LA's Hollywood? Are there really no psychological scars, no fatal flaws?

The first hint that Mendes might not be the uncomplicated charmer he is so often presented as comes from his choice of material. At first glance, there seems to be no pattern to the plays and movies he has chosen to direct. He famously selects projects which are eclectic – this year he gives us a gangster movie (The Road to Perdition, released last Friday), but he seems just at home directing the twee musical Oliver! at the London Palladium, American Beauty, a satire on US suburbia, or a play set on the battlefields of the First World War, And to the Green Hills Beyond. In this mixed bag, there seem to be no clues to the real Sam Mendes.

But, emerging from this wildly divergent choice, there are two artists Mendes revealingly returns to as a director time and time again: Anton Chekhov (his production of Uncle Vanya at London's Donmar Warehouse also opened last week) and Stephen Sondheim. Both men depict characters who find themselves bitingly unhappy without ever quite knowing why. As one character says in Brian Friel's terrific new translation of Vanya, "We are not sure what we expect from life, but it disappoints us." This could be the root of the director's questing, ever-gnawing ambition.

Mendes' identification with the characters of these bleak writers sometimes pokes through into the public realm. Can it be coincidence, for example, that the then-bachelor Mendes, emerging from a series of broken relationships in his early thirties and hung up about marriage, chose five years ago to direct the Sondheim musical Company, which is about, er, a bachelor in his early thirties emerging from a series of broken relationships and who is hung up about marriage?

Chekhov's characters famously pine for Moscow, which serves as an all-purpose metaphor for lost security and dying dreams. So where does Mendes' close identification with this melancholy stem from? What has the man who seems to have risen inexorably to the very top ever lost? The obvious answer is his father. When Sam was just nine, his university lecturer father Peter Mendes walked out of the family home. Although Sam has recently tried to dismiss the "myth of my unhappy childhood", in earlier and more candid interviews he talked about the damage his parents' break-up did to him. "When you become your own parent at the age of nine, you get a lot of practice at being the boss of your own life," he said. He then added: "I also became the parent of my mother," implying that Valerie Mendes was unable to cope with her young son. It is a sign of how important that difficult relationship remains to him that she was his date to the Oscars last year.

Mendes admitted that the character he most identified with in his film American Beauty – for which he won an Oscar for best director – was the alienated teenage daughter. This was a girl without bearings and certainly without responsible or sane parents. "It's the most personal thing I've ever done," he commented. "Without wanting to sound rude about it, my own family was not entirely functional." He later confessed to an interviewer that throughout his teenage years, "I was a troubled fantasist. I was escaping from my parents' divorce. It was just me and my mother, so I lived in my head a great deal of the time."

The ripples from that parental relationship obviously worry him today, as he tries to settle down into a relationship with the film actress Kate Winslet and her four-year-old daughter Mia. He leaves behind him a string of dumped, disappointed actresses, including Rachel Weisz and Calista Flockhart – before she became famous for her role in Ally McBeal. His mother has said his new relationship is "perfect – you should hear the joy in his voice". But Mendes is plainly still cautious, and still insists that "I don't believe in marriage. People from broken homes just don't buy it."

It seems that Mendes' personal life is plagued by the same mood that hangs over so many of his plays and movies: impending doom. The only common thread running through almost all the projects he has chosen is a sense that disaster is waiting just around the corner. Chekhov's characters are all about to be wiped out by Lenin's revolution (so long as their own nervous systems don't implode first); the cast of Cabaret is hurtling unknowingly towards Auschwitz; the characters of Assassins are left screaming "Where's my prize?" into the ether, knowing that it will never come. The list goes on.

If his parents' break-up is essential to understanding Mendes, then another – and much neglected – phase of his life is just as important. He has always said that he can cope with the poison and stress of Hollywood and Broadway because "nothing has ever been as bad as Cambridge. Your peer group – all jockeying for position – is far more frightening than any authority figure." As a student at Peterhouse, Mendes was immediately drawn to the drama scene which revolved – then as now – around the ADC Theatre. Ian Shuttleworth, now a Financial Times theatre critic but then an actor in one of Mendes' shows, explains: "The mood in Cambridge drama back then wasn't so much bitchy or malicious. It was that very 1980s climate of careerism." In that milieu, where "Sam was quite obviously the business, and didn't exactly have to struggle", Mendes inevitably attracted a considerable degree of resentment and envy.

Yet there is no denying that this was a constructive period for the young director. It was the time in his life when the fantasies of his teenage years began to take a constructive role, as he projected them outwards on to the stage. Before then, his all-consuming ambition had no focus. While he was still at school, for example, he wrote in a cricket tour programme that his ambition was simply "to be remembered by many".

Mendes has self-deprecatingly described himself, with more than a ring of truth, as a quintessential product of the "Oxbridge confidence machine". The man we see today emerged almost fully formed from Cambridge. Within a few years of graduation, he was directing stars such as Paul Eddington, and then took Judi Dench in The Cherry Orchard to the West End. It was in Cambridge that he developed the skills that are the key to his directorial success: his almost-Clintonian charm, his extraordinary diplomatic ability (so necessary in a collaborative medium like film) and the talent to sustain what he calls "the confidence trick" of directing: seeming to know what you're doing even when everything is going wrong.

Yet – as with the entire school of successful theatre directors to emerge from Cambridge in the past 30 years, especially Trevor Nunn and Richard Eyre – the confidence seems to veil a neurotic unhappiness. Despite his Oscar, his millions, his gorgeous girlfriend and ability to secure a green light for any project he fancies directing, Sam Mendes still appears an unhappy man. It seems that he will always be left pining for a Moscow he can never reach.