One newspaper last week cast Cameron in a homage to the famous blue-and-red image of President Obama, over the words "Our Only Hope." In contrast, another ran a photo of him as a rich young Oxford University student, haughty in stiff collar and tails.
On one hand, Cameron is a modern urbanite who has tried to remake his party in his own image as an eco-friendly, down-to-earth man of the people who rides his bike to work. Yet he's also the privileged product of Eton, Britain's most elite private school, and Oxford University - and is married to an aristocrat's daughter.
At 43, Cameron is the youngest prime minister in almost two centuries, a few months younger than Tony Blair was when he became leader in 1997.
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Sometimes called the "Tory Blair," Cameron has dragged the Conservatives back from the wilderness to which they were consigned by Blair's Labour landslide, moving his right-of-center party toward the center of British politics, promoting inclusive politics, environmental concerns, and a certain modern sensibility.
He's recruited more women and minorities, declared his loyalty to public services and - gingerly - tried to draw the Tories from under the shadow of Margaret Thatcher, the polarizing leader who dominated British politics in the 1980s.
He apologized for the Iron Lady's refusal to back sanctions on South Africa's apartheid regime, softened her skeptical position toward Europe and embraced Britain's state-funded National Health Service. And his support for the health service was heartfelt. Cameron and his wife Samantha were parents to a severely disabled son, Ivan, who required constant care and died last year aged 6. The couple have two other children, and Samantha Cameron is expecting a baby in September.
"We have to change and modernize our culture and attitudes and identity," he told activists shortly after becoming party leader in 2005. "When I say change, I'm not talking about some slick re-branding exercise. What I'm talking about is fundamental change ... that shows we're comfortable with modern Britain."
But in a country where class conflict is rarely far away, Cameron's background had been seized on by his opponents as a liability.
Born into a wealthy family with an aristocratic pedigree, Cameron studied at Eton College, the breeding ground for more than a dozen prime ministers, and a bevy of royals and foreign leaders besides. A successful tenure at Oxford was followed immediately by a job with the Tories.
Cameron spent several years working his way up the party hierarchy before moving to the business world, working as a spin doctor at television company Carlton, whose boss Michael Green once described him as "board material."
"I tried to persuade him that he could have a really good career in industry, but he was completely resolute about going back to politics, and I respected him for that," Green was quoted as saying in The Independent. "He's good, he's the real McCoy."
Other journalists demurred, accusing Cameron of being slippery and unpleasant.
Cameron made his move back into national politics in 2001, winning the safe parliamentary seat of Witney. The Oxfordshire constituency is dotted with rural market towns, and its posh profile matches that of its representative.
Independent on Sunday deputy editor James Hanning said that Cameron is "undoubtedly be the most privileged person to become prime minister since Alec Douglas-Home," a Conservative earl who served as prime minister more than half a century ago.
British Prime Minister Gordon Brown repeatedly mocked Cameron's upbringing, telling lawmakers last year that the Conservative chief's economic plans had been "dreamt up on the playing fields of Eton." The Tory leader - full name David William Donald Cameron - has countered by asking supporters to just call him Dave and playing up his taste for Guinness and darts.
Cameron himself has acknowledged that his path to power was smoothed by privilege, but Hanning, the author of "Cameron: The Rise of the New Conservative," said the politician never apologized for his background.
"He's the most extraordinarily grounded person," said Hanning, who is the deputy editor of the Indep. "To him, his background is normal. He shrugs it off."
Cameron's victory is a vindication of his overhaul of the Conservative Party, which in recent years seemed out of touch and headed toward irrelevance. He also had the luck to come in when the public was tiring of Labour, in power since 1997 and presiding over the worst economic downturn in decades.
Cameron had already spent several years working in Tory politics before he became a member of Parliament in 2001. At the time, the party was riven by internal dissent and struggling to find an answer to Blair - who retained considerable popularity before his decision to back the U.S.-led invasion of Iraq.
Shortly after his election, Cameron argued that his party needed "to change its language, change its approach, start with a blank piece of paper and try to work out why our base of support is not broader." Cameron's call for a rethink began to resonate after Tory attempts to attack Labour on traditional issues such as immigration and European integration fell flat.
Meanwhile, Cameron was swiftly rising through the ranks, serving in a variety of roles before he was promoted to be his party's spokesman on education. When Conservative leader Michael Howard stepped down in 2005 following the party's third successive election defeat, Cameron seized his chance, winning a long-shot bid for the Tory leadership.
Cameron went to work, redesigning the party's logo - dropping Thatcher's blue arm gripping a flaming torch - and subbing a more innocuous-looking green tree against a white background. Critics groused that it looked like a piece of broccoli, and the grumbling grew louder as Cameron began dismantling parts of Thatcher's legacy.
Cameron also began aggressively reaching out to young multiethnic professionals to replace some of the crusty grandees who populated the Tories' back benches in the House of Commons.
Some were unhappy.
"Trying to change, perpetual change - I don't think it's necessarily a good thing," said Norman Tebbit, employment minister under Thatcher and a member of the Tory old guard. Bernard Ingham, Thatcher's former press secretary, even wondered whether Cameron was really a Conservative. A handful of disgruntled lawmakers defected to the United Kingdom Independence Party, which wants to remove Britain from the European Union.
On the left, Cameron faced skepticism from those who doubted the Tories had really changed.
Some of his attempts to position the Conservatives as the party of the environment and social justice had a distinctly awkward feel. Most memorable was Cameron's practice of biking from his home in west London's Notting Hill to Parliament - it emerged that his briefcase and shoes were being ferried to work separately in a chauffeur-driven car.
Cameron managed to keep his cool, scoring points against the prime minister in their weekly clashes in Britain's House of Commons and putting in polished appearances on the campaign trail.
In an interview with the Daily Mail published Wednesday, Cameron made a last-minute appeal to the Tory base to back his reforming mission.
"We weren't being listened to," he said. "We could have stood naked on the building tops and shouted but no one was listening."
In the end, the British public half-listened - leaving Cameron just short of a majority and saddling his government with ministers from the Liberal Democrat party, whose center-left politics clash with the Tories on key issues.