Rent Falling Up (2009)

Henry O'Shea (Joseph Cross) is on his way to a nursing degree until his dad's sudden death forces him to take a job as a Manhattan doorman. But no amount of warnings from his high-strung boss or laid-back co-worker (Snoop Dog) can prevent Henry from breaking Rule #1: Never fall for the beautiful daughter (Sarah Roemer) of one of the building's wealthiest tenants. In a world where rich snobs never mix with minimum wage slobs, can a romance between a regular guy from Flatbush and a 5th Avenue rich girl even make it past the front door? Annette O'Toole, Rachael Leigh Cook and Mimi Rogers co-star in this surprising comedy about working hard, dreaming big and knowing when to let the right one in.