Tricky Business is a 2017 American comedy action movie directed by Tim Miller and starring an ensemble cast headed by Chris Pine, Jennifer Lawrence, William Shatner, Morgan Freeman, Gary Sinise, and Kevin Costner. It is based on the Dave Barry book of the same name and, like most of Barry's fiction, follows a diverse group of people throughout their experiences on a single cruise ship sailing out of Miami.
The Extravaganza of the Seas, a modest-sized cruise ship operating an illegal casino inside which heads out of the United States' territorial waters to carry out its illegal activities, is preparing to cast out of Miami despite the fact that a tropical storm is barreling down the East Coast. Cocktail waitress Fay Benton (Lawrence) bemoans the fact that she has to work odd hours to make ends meet while her mother tells her off for her decision by comparing her to her more respectable middle-class sister. Wally Hartley (Pine), a down-on-his-luck 35-year-old band frontman living with his mother after he broke up with his fiance (who was having an affair with his boss from an attempt to hold a white-collar job), gets called to perform on the Extravaganza with his band despite the storm. In the Beaux Arts Senior Living Center, Arnold Pullman (Shatner) and Phil Hoffman (Freeman) plot to escape the retirement home and the watchful eye of the assistant day manager to get on board the Extravaganza and gamble, also despite the storm barreling down Miami. Arnie and Phil's plot to escape the retirement home is nearly foiled by Mrs. Krugerman, an old lady who has a crush on Phil. Mrs. Krugerman traps Phil with her walker so Arnie decides to do what needs to be done and kisses Mrs. Krugerman, surprising her enough that she releases Phil, which allows the two old men to escape the retirement home.
Over in the Bahamas, where the storm is already wreaking havoc, Frank (Pratt) and Juan (Peña) walk up to a speedboat while talking about how the weather won't dissuade their bosses from doing the drop as planned. They are greeted on the boat by Tark (Sinise) who tells Frank and Juan that the regular Bahamians handling the drops won't be available so he decided to bring along some help of his own: Kaz (Cable Guy), Rebar (Cudmore), and Holman (Courtney). Frank and Juan immediately don't trust the new guys and Frank warns Tark not to try any funny business or else he will personally shoot Tark.
Wally and his band Johnny and Contusions, consisting of him and his fellow reefer addicts and friends Ted (Quinto), Johnny (Cho), and Jock (Pegg), arrive at the dock after a discussion about homeless people who ended up owning real estate in Hawaii through late-night infomercials. There they are greeted by Fay and Mara (Smulders), cocktail waitresses who were themselves having a conversation on how they ended up working this particular job before Johnny and the Contusions arrived. Wally is immediately smitten with Fay and tries to strike up an intelligent conversation but can't come up with anything better than "The weather sucks, huh?" Arnie and Phil are next to arrive, followed by a man in a conch shell suit coming out of a limo. The limo driver tells the Extravaganza crew that the boss wanted to promote his restaurant so Conrad Conch gets a ride on the ship.
Johnny and the Contusions perform easy listening music while the ship's patrons wait for the Extravaganza to finally get out of US territorial waters so they can finally gamble. During a break, Ted proves that the ship's chef Emeril (Trejo) recycles his food when he finds a baseball card he slipped into one of the buffet dishes over a week ago and wins a band-wide bet that the food Emeril served last week was the same food he served tonight. The band then start a new betting pool on how much longer the card will remain in the dishes. Eventually a gaggle of women celebrating the divorce of one of their number make their way into the entertainment room and Johnny and the Contusions begin performing party music, only to be spoiled by the floating casino's pit boss Manny Arquero (Dacascos), who has a pathological need to tell people to "shut the fuck up" and tells the band to play quieter so that no one will hear them even through the storm. Before the girls leave, Connie (Chopra) the divorcee drops a condom on Jock's drums.
Meanwhile, back on the drug runner from the Bahamas, Frank orders Kaz and his cohorts to keep to the cabin and has Juan watch over them. But Juan gets seasick and has to hurl and soon everyone else except for Tark is throwing up. Kaz, despite being weak from seasickness, takes advantage of Frank's situation and knocks both him and Juan out. Tark finally takes his revenge on Juan by cutting off the Latino's nose and then his testicles before throwing Juan overboard. Frank is tied up and made to witness the mutilation of Juan by Tark and then Tark promises Frank that more is to come for him.
The crew of the Extravaganza prepare to transfer the funds from their cruise ship to Tark's boat. Arquero and First Officer Hank Wilde (Gordon-Levitt) supervise the transfer. Arquero notices that only Tark is visible on his boat and that Frank and the regular Bahamians are not around. Tark says that Frank is seasick but Arquero takes this to mean that Frank should be up on the deck hurling if he was seasick and he prepares to take out Tark, whom he has suspected of being a complete rat all along. Suddenly, Arquero gets shot in the back, allowing Tark to shoot the rest of the crew taking part in the transfer, including Wilde. Arquero's shooter is revealed to be Conrad Conch, who is also reveated to be Bobby Kemp (MacNicol), owner of the Extravaganza and a man with a grudge against both Arquero and Arquero's boss Lou Tarant.
Ted, Johnny, Arnie, Phil, and Fay all witness the shooting and all of them attempt to warn other people of the carnage happening in the back of the ship. Arnie and Phil go to Mara and the ship's bartender Joe Sarmino (Bratt) to tell them about the shooting while Fay bumps into Wally once again and asks him to lead her to the bridge. Meanwhile, Tark and Kemp get into a dispute on how to distribute the takings. It is revealed that Tark thought of the whole double-cross plan and only brought in Kemp to get Tarant off of Tark's scent when word of the double-cross inevitably gets to the gangster until it reaches a point where Kemp believes that he was the one who came up with the double-cross in the first place. Tark kills Kemp and dumps his body in his boat to complete the illusion of a double-cross. Back in Miami, Lou Tarant (Clarke) gets word that Kemp has been spotted on the Extravaganza and orders a boat out so he could "talk" to Kemp himself, not knowing that Kemp was already dead at the hands of the real mastermind of the double-cross.
Ted and Johnny reach the bridge first and inform Captain Eddie Smith (Costner) of the chaos happening at the back of his ship. Kaz then gets to the bridge and stops Captain Smith from calling for help. Fay, Wally, Mara, Arnie, and Phil all arrive at the bridge soon after that, leaving Kaz with a nightmare to deal with so many hostages. Fay suddenly brings out a gun and orders Kaz to cease and desist, revealing herself as a Coast Guard Investigative Service agent. Fay's stand doesn't last long before Holman arrives to back Kaz up and the two make a show of saying that the heist was the brainchild of Bobby Kemp as per Tark's plan and then Kaz shoots the radios and Captain Smith. He then tells everyone else on the bridge that whoever tries to get out will get shot in the head. While all this is going on, Jock and Connie are busy having sex in the ship's kitchen, at least until Tina (Wilson), Jock's current girlfriend, goes into the kitchen to search for him. Tina finds Jock and Connie, both stark naked, and after Jock fails in an attempt to reason with Tina, he is chased out of the kitchen and into the casino area by a knife-wielding Tina.
- Chris Pine as Wally Hartley, a down-on-his-luck 35-year-old living with his mother and scraping a living as the frontman of the band Johnny and the Contusions
- Jennifer Lawrence as Fay Benton, a cocktail waitress onboard the Extravaganza of the Seas and also secretly an undercover agent of the Coast Guard Investigative Service
- William Shatner as Arnold Pullman, an 83-year-old now living in the Beaux Arts Senior Living Center in Miami who routinely sneaks out of the retirement home to go to the casino onboard the Extravaganza of the Seas
- Morgan Freeman as Phil Hoffmann, an 81-year-old retiree who is Arnold's best friend and only friend in the retirement home and also accompanies Arnold to the Extravaganza of the Seas
- Gary Sinise as Tarquin "Tark" Bronson, the captain of a drug runner operating between the Bahamas and the Extravaganza of the Seas who has his own plans for the product and money he transports
- Chris Pratt as Frank Nicholas, Tark's contact with the operation on the Extravaganza of the Seas
- Michael Peña as Juan Sepulveda, Frank's Latino second-in-command
- Kevin Costner as Eddie Smith, captain of the Extravaganza of the Seas
- Zachary Quinto as Ted Brailey, keyboardist of Johnny and the Contusions
- John Cho as Johnny Clarke, bassist of Johnny and the Contusions and the inspiration for the band's current name
- Simon Pegg as Jock Hume, drummer of Johnny and the Contusions and the band's "lady's man"
- Jason Clarke as Lou Tarant, the mysterious "frontman" of a large drug-smuggling and money-laundering operation happening onboard the Extravaganza of the Seas
- Peter MacNicol as Bobby Kemp, the unscrupulous south Florida businessman who ends up getting involved in Lou Tarant's operation by virtue of buying the Extravaganza of the Seas
- Cobie Smulders as Mara Purvis, another cocktail waitress on the Extravaganza of the Seas and Fay's workmate
- Mark Dacascos as Manny Arquero, Extravaganza pit boss and supervisor of the ship's offshore transfer operations
- Benjamin Bratt as Joe Sarmino, a Cuban bartender on the Extravaganza
- Larry the Cable Guy as John "Kaz" Kazarstsky, an ex-con whom Tark brings aboard his boat for the "transfer job"
- Daniel Cudmore as Rebar, one of Kaz's accomplices
- Jai Courtney as Holman, Kaz's other accomplice
- Joseph Gordon-Levitt as Hank Wilde, first officer of the Extravaganza and Lou Tarant's eye on Captain Smith
- Snoop Dogg as Nestor, a Jamaican who sells pills given to him by Arnold and Phil from Beaux Arts and drives them from Beaux Arts to the Extravaganza
- Kurtwood Smith as Dexter Harpwell, the strict assistant day manager of Beaux Arts
- Rebel Wilson as Tina, the roulette girl who is Jock's latest "date" and also a notorious farter
- Priyanka Chopra as Connie, the divorcee who goes out and "does it" with Jock in the middle of a gig
- Danny Trejo as Emeril, the chef of the Extravaganza who is suspected of recycling his own food
- Carrie Fisher as Mrs. Sally-Louise Krugerman, an old lady living in Beaux Arts with Arnold and Phil
- Stone Cold Steve Austin as Stu Carbonecca, owner and driver of one of Tarant's drug runner boats