Lighthouse Hill (2004)

It is very hard to grow up rich.  Ok, not really.  It is definitely hard to grow up poor.  The film focuses on the growing up part of what is hard about being rich.  Charlie (Jason Flemyng) is a successful London publisher, but he is constantly in the shadow of his wealthy overbearing mother.  She is in every corner of his life--his work, his love life, his business interactions, and she wants to continue to control it all.  So while he is headed into middle age, he is not free of his family of origin.  He is engaged to be married, but it becomes very clear that his mother is more in love with his fiancee than he is.

He takes out an ill advised loan from a loan shark to launch a business with his close friend--the loan comes due, he doesn't have the money, his friend gets hit by lightning and dies, all more or less on the same day.  He refuses to go to his mother for help with the loan repayment, and he hits the road once he is roughed up by a couple of intimidating women who are his loan shark's enforcers.  Before you know it he has stumbled upon a curious old hotel, with a nearby semi-restored amusement park and a bevy of oddball locals, including the enchanting Grace (Kirsty Mitchell). 

Initially the allure is just how hidden he is amongst this crowd, but as time goes on, he starts to fall for the people and the place.  They do not treat him like the boss, they do not suck up to him because of his money and class, and they do encourage him to follow his dreams.  Which he has a very hard time doing--much of the movie is the false starts that he makes in searching for his bliss.  But remember, this is a British comedy, and a happy ending is mandatory.  Very fun and quirky movie.