In the mid-1990s, Leonardo DiCaprio cemented his place both in the hearts and on the walls of a generation of teenage girls. His portrayal of one half of the Bard’s star-crossed lovers in Romeo and Juliet, and as Jack Dawson in Titanic, alongside Kate Winslet, saw him become one of our generation’s heartthrobs. His boyish face and curtain fringe, a look I had attempted to share at the time, were the makings of a star.

So what of DiCaprio now? How has the boy actor transformed into one of Hollywood’s leading males? DiCaprio is an actor guaranteed, not only to boost box office figures, but to simultaneously garner critical acclaim. A three-time Academy Award nominated and Golden Globe winning actor, this is thus far the peak of a dizzying career. DiCaprio continued his engagement with difficult material by starring in Sam Mendes’ adaptation of Richard Yates’ 1961 novel, Revolutionary Road. It was also a return to his partnership with Kate Winslet that drew so many tears in Titanic.

It has been said countless times before, but DiCaprio is not what you expect to meet. Standing at a good six feet and well built, this isn’t the baby-faced Jack Dawson of Titanic. DiCaprio really looks the part of a Hollywood actor. No longer pretty, he is now decidedly handsome, the childishness of his face hidden now behind a beard, admittedly one of the cultivated type a la Craig David.

DiCaprio is immensely amiable, especially for a man deep into the trail of hundreds of interviewers asking the same questions. What is more, he comes across as a highly intelligent artist. His understanding of his part and the themes of the film are exemplary of a young actor, and his drive to make a very good film is deeply apparent.

Although DiCaprio admits that he never read the original novel prior to the film, as few have, Yates’ novel remains very much an undiscovered masterpiece, he said that on reading both the script and the original he realised why ‘so many people take the novel into their lives.’

The film follows, in DiCaprio’s words, the failure of a couple’s ‘individualism in a very contained world.’ In this respect, it followed a particular interest of DiCaprio’s to present the stories of individuals, and their own personal struggles, a theme he sees as overlooked in the blockbuster world of Hollywood. The film has an almost theatrical feel to it, something that DiCaprio acknowledged and relished. He talks enthusiastically of the fact that the film was shot chronologically, something that is rarely afforded by the time and financial constraints of Hollywood.

The headline puller of DiCaprio’s new venture is, of course, the return of ‘Leo and Kate’, the global phenomenon of remarkably over twelve years ago. For DiCaprio, besides the obvious trepidation of returning to old ground, the prospect of working with Winslet again seemed one of real satisfaction. DiCaprio is highly complimentary of his co-star and friend, a Golden Globe winner for this film just a week or two ago. His admiration of her commitment to her work is very evident, he notes that through her Titanic days to now she has ‘an intense work ethic, she always wants to make a great work, she has a real desire to make great films, it’s just part of her DNA.’

Although the film may see criticism for its ponderous pace, one that sees it feel even mildly turgid at times, the pairing of Leo and Kate pulls it above these considerations. This pairing is one that both actors have sought to return to ever since Titanic.

‘There were a few projects through the years, we would ring each other up with them,’ DiCaprio tells us. However, the shadow of Titanic, despite being a film that he is very proud of, loomed over the partnership. In this respect Revolutionary Road presented the perfect pairing. Leo and Kate’s dysfunctional relationship is a far sight from the brief romance and tragedy of Titanic, whilst still offering an opportunity for these two friends and highly talented actors to revisit an undeniable on-screen chemistry.

For DiCaprio, Revolutionary Road is another in a series of very serious roles. From his recent collaborations with Martin Scorcese in Gangs of New York, The Aviator and The Departed to Edward Zwick’s Blood Diamond and Ridley Scott’s Body Of Lies, Leonardo DiCaprio is an actor continually extending himself. I questioned this resolve to make difficult films and asked him when he last played a role that he found light and easy. Laughingly he said that it has been ‘hard work recently’ but on meeting such a committed actor one feels that this is what drives him. His pick for a genuinely easy-going experience comes from a little remembered Woody Allen collaboration, Celebrity in 1998. DiCaprio has for all of us Allen-ites a quintessentially Woody Allen memory. Remembering his directorial style, whilst affecting a very convincing Woody Allen inflection, he recollects the extent of Allen’s direction as being, “You can stand over there … but you don’t have to.”

It is not often that DiCaprio gives himself a break; he has to look back over ten years ago to a film that he found easy. His performances betray one of the greatest and most compelling actors of our generation. The Academy Award he has deserved since What’s Eating Gilbert Grape in 1993 may evade him still but it can’t be far off now. With his commitment and pedigree we may well be looking at the next De Niro, Pacino or even Brando here. Let us just hope that he remains the same charming man who put a smile on my face as I stepped out of the Dorchester’s revolving doors, before returning to the biting cold of a January day and the real world.

If I were to ask you what you associate with Cuba, you would probably reply something along the lines of: cigars, missile crises, a certain man named Fidel Castro. Indeed, it was armed with such expectations and vaguely recalled pictures of “El Comandante” smoking an absurdly long cigar in his green military fatigues that I, with the family in tow, ventured out to Cuba for Christmas.

One of the first things I learnt about Cuba before I went was that its motto is “Patria o muerte” (Fatherland or Death). That‘s quite an intimidating introduction, yet as soon as I arrived, my expectations were confounded. Cuba’s turbulent history has made it into one of the most eclectic and culturally diverse countries in the world.

To some extent, the Cuban experience is a surreal one. Nowhere else in the world can you see traffic jams in which 1950s Classic American cars are driven side by side with rickety old Soviet Lada and Zhiguli models. Nowhere else in the world can you see such a syncretism of African and Spanish cultures in both the religious and musical spheres. Driving in to Havana is like driving onto a slightly decrepid film set. The city is divided into both old and new quarters with dusty 19th century Iberian houses being punctuated by imposing modern constructions. Ernest Hemingway, who lived here for 22 years of his life, wrote that “In terms of Beauty, only Venice and Paris surpassed Havana”.

As with many countries who adopted the socialist model, Cuba has a high literacy rate and a low rate of violent crime. There is no private ownership and you cannot sell your house since it does not technically ‘belong’ to you. Mobile phones are a luxury and you still see long queues at internet centres as locals wait to get online. However, this is not the stern-faced bureaucratic socialism of Eastern Europe. It was incredible to see how much Cubans express themselves vibrantly through dance, religion, music and art. The Buena Vista Social Club hails from Cuba and you can hear the wonderful ‘Chan Chan’ in many streets after dark. One night we stumbled across a mass outdoor fiesta. There must have been over 200 couples enthusiastically dancing to the drumbeat rhythm of the Salsa music – quite an experience for any unsuspecting witness.

Ever since Christopher Columbus crossed the Atlantic and discovered both the Americas and Cuba in 1492, the country has only truly had self-governance since the 1959 revolution. It was under colonial rule of the Spanish from 1492 to 1898 (which included an 11-month occupation by the Brits), and controlled, by proxy, by America until 1959. This was the year that a pair of young revolutionaries by the names of Fidel Castro and Ernesto “Che” Guevara swept into Havana, overthrowing the American backed Batista government. Since that day, Castro has survived over 638 assassination attempts which have included bizarre efforts by the CIA to kill him with exploding cigars, fungal-infected scuba-diving suits, and mafia-style shootings. You have to respect the man for continuing to puff away at his Cohibas.

After the Revolution, Castro expropriated private property and nationalised many industries in a move towards socialism. Some of these industries were American and, as you can imagine, the US was far from delighted by such treatment. In 1961, the US government tried to overthrow Castro by landing about 1400 military trained Cuban – American immigrants on the Bay of Pigs. However, they were defeated and captured. This spectacular failure on the part of the Americans pushed Cuban – American relations to an all time low and in 1962 the US government imposed a trade and travel ban to Cuba for all its citizens, which still is in effect today. Later that year, the Cuban government allowed the Soviet Union to put nuclear missiles pointing in the direction of their northerly neighbour causing the Cuban Missile Crisis and almost prompting World War Three.

I was reminded of Cuba’s Soviet past when I saw an enormous Russian warship which had anchored in Havana harbour on its way to do joint exercises with the Venezuelan navy. Hundreds of barely adolescent Russian sailors were walking in columns in one of the nearby squares, with many of them enjoying the delights of Cuban ice cream. A Ukrainian street vendor told me how he had been sent out to Cuba before the fall of the Soviet Union and had been left there, unable to afford a return ticket. It was a surreal encounter but a reminder of Cuba’s eastward looking past.

One thing which is noticeable more than anything else is the iconic image of Che Guevara’s face – on just about every tourist t-shirt and billboard. Even on the beach, a sunburnt Brit played volleyball with Che’s face tattooed on his not-so-muscular left peck. I am pretty sure that this is not exactly what Che envisaged when he started the revolution and I don’t think he would be too happy either knowing that his face had been adopted by the capitalist consumer culture and plays a crucial part in every gap year traveller’s wardrobe.

You may wonder why, if the Cold War is over and Cuba no longer presents a threat to American interests, the embargo still exists. Well, in Florida the Cuban-American lobby is extremely powerful. It is composed of emigrants from Cuba who oppose any sort of normalisation of relations due their hostility to the regime. The embargo detrimentally affects the lives of Cuban citizens. They can’t use dollars, they can’t export to America and the economy is being deprived of both American investment and American tourism. There are many highly educated Cubans who are forced to work as taxi drivers or vendors because of the lack of employment opportunities. Fortunately, the incoming Obama administration has made positive noises about lifting the embargo. If this is done, then the country will change beyond recognition as it boards the capitalist train.

Such changes will include a reduction in the number of wonderful 1950s classic American cars on the roads, as Cubans import newer models which they have not been allowed to do since 1959. The country will be forced to modernise and doubtless Ronald Macdonald will become a permanent Cuban citizen. Many of the crumbling 19th century houses will be demolished to make way for development and a visit to Havana will become a simple weekend trip for most Americans (it is only 90 miles from Miami). Cubans will undoubtedly benefit greatly from these changes and the strong pull which memories of the revolution exert on Cubans will weaken when the ailing figure of Fidel Castro passes away. All I can say, is that you must visit this wonderful country before it is brought out of isolation as, safely discounting North Korea in terms of tourist appeal, it is one the few socialist countries left in the world, and a beautiful, surreal and fascinating one at that.