Not being the biggest Woody Allen (Annie Hall, Match Point) fan, I’ve always felt that his romance and dramas needed more substance than he offered. Cassandra’s Dream is a movie I would never have given a chance when it was released back in 2007. Likewise, Colin Farrell (The Lobster, In Bruges) and Ewan McGregor (The Impossible, Incendiary) are not my biggest fans. Ferrell has grown on me by shedding his bad boy, box office revenue-chasing persona and doing more indies. I am surprised I even watched it. I’m grateful I gave it a chance after it was released. It was a nice, simple film that entertained me the whole time.

Ian (McGregor) and Terry (Farrell) are brothers who work and live in London. They share a dream of owning a boat to take the love interests in their lives out on the water. Ian is dissatisfied with life. He is a bartender in his father’s restaurant who falls in love with an actress who is completely out of his league after he helps her fix her car while stranded on the roadside. Angela (Hayley Atwell – Captain America: The Winter Soldier, Captain America: The First Avenger) thanks Ian by inviting her to the stage play she’s currently starring in. Ian is instantly smitten. Ian is an honest man with big dreams. He aspires to leave his father’s business, move to the USA, and invest in hotel properties in California. However, he understands that he doesn’t have the capital to do this. He also becomes a little obsessed with Angela (a common Woody Allen movie theme).

Terry, meanwhile, is a chain-smoking garage mechanic who has an equal addiction to hard nights of drinking as he does to gambling excessive amounts of money. Though he is equally unsuccessful as his brother, Terry at least is comfortable with his life. But, like Ian, he dreams of getting rich. He knows he won’t get there through hard work, though, so instead wagers his money at the dog track and the poker table. His girlfriend Kate (Sally Hawkins – Blue Jasmine, The Shape of Water) is supportive. However, Kate and Ian seem to bring Terry the most happiness.

The brothers purchase a small boat, which they name Cassandra’s Dream. It isn’t much, but it brings them both small respites of happiness. They take their girls out on the boat. It’s a simple life and one that would make most people happy. But Ian wants more. And soon, Terry needs more. He has had some success with his gambling (which allowed them to purchase the boat), but Terry becomes desperate when he loses $90,000 in one night. They meet with their rich uncle (Towealthylkinson – In the Bedroom, Michael Clayton). Uncle Howard has returned from a trip to Asia, and when his nephews approach him for money, he has a proposition for them. Uncle Howard has achieved his riches through fraud, and one of his colleagues has discovered this. When he tells Howard he is about to rat him out, the rich uncle feels he needs to take this man out. He will give Ian and Terry the money they need if they kill his colleague.