Romantic drama starring William H. Macy as Bernie Lootz, a lonely middle-aged man with terrible luck who owes the Shangri-La casino in Las Vegas, owned by old-fashioned mob boss Shelly Kaplow (Alec Baldwin), over $100 000. To repay his debt, he works for Shelly as a 'cooler' - someone who plays alongside high rollers to stop them from winning too much. His life takes a turn for the better when he falls in love with cocktail waitress Natalie (Maria Bello), and he experiences real happiness for the first time in years. But when his luck starts to spill over onto the gambling floor, Shelly is none too impressed, and sets out to sabotage the most important thing in Bernie's life: his relationship with Natalie.

Demi Moore plays Laura Quinn, a bright, driven and beautiful executive at the London Diamond Corporation who finds herself frustrated by a glass ceiling after years of faithful employment, as man after man is promoted ahead of her despite her greater experience.

Michael Caine is Hobbs, the nighttime janitor at London Diamond who is virtually invisible to the executives that work there, but over the years has amassed a startling amount of knowledge about how the company runs. Hobbs has his own bone to pick with London Diamond.

Observing Laura’s frustration, he convinces her to help him execute an ingenious plan to steal a hefty sum in diamonds. But unbeknownst to Laura, Hobbs plans go even farther than he’s let on, and together they set in motion a thrilling heist of dizzying proportions, the likes of which London has never seen.