Tony Lip, a bouncer in 1962, is hired to drive pianist Don Shirley on a tour through the Deep South in the days when African Americans, forced to find alternate accommodations and services due to segregation laws below the Mason-Dixon Line, relied on a guide called The Negro Motorist Green Book.

When timid bank clerk Stanley Ipkiss discovers a magical mask containing the spirit of the Norse god Loki, his entire life changes. While wearing the mask, Ipkiss becomes a supernatural playboy exuding charm and confidence which allows him to catch the eye of local nightclub singer Tina Carlyle. Unfortunately, under the mask's influence, Ipkiss also robs a bank, which angers junior crime lord Dorian Tyrell, whose goons get blamed for the heist.

Jimmy "The Tulip" Tudeski now spends his days compulsively cleaning his house and perfecting his culinary skills with his wife, Jill, a purported assassin who has yet to pull off a clean hit. Suddenly, an uninvited and unwelcome connection to their past unexpectedly shows up on Jimmy and Jill's doorstep; it's Oz, and he's begging them to help him rescue his wife, Cynthia.

Hell's Kitchen, New York. Terry Noonan returns home after a ten-year absence. He soon reconnects with Jackie, a childhood friend and member of the Irish mob, and rekindles his love affair with Jackie's sister Kathleen.

On her deathbed, a mother makes her son promise never to get married, which scars him with psychological blocks to a commitment with his girlfriend. They finally decide to tie the knot in Vegas, but a wealthy gambler arranges for the man to lose $65K in a poker game and offers to clear the debt for a weekend with his fiancée.