I Love You Phillip Morris (2009)

A con man comes out of the closet and meets his true love in jail in I Love You Phillip Morris (2009). Steven Russell (Jim Carrey) was a police officer and devoted family man--until a brush with death made him realize his life was a lie. Steven's new YOLO attitude led him to come out of the closet and, less commendably, to go on a spending spree with other people's credit cards. The ensuing fraud conviction lands him in the slammer, where the meets soft-spoken Phillip Morris (Ewan McGregor) and falls madly in love. Speaking of the slammer, not only to we get to see Jim in fishnets and heels a minute in, we also get to see him slamming away as he tops mustachioed actor Donovan Guidry. Who needs the Marlboro man when you've got guys this smokin'?