Masquerade (1988)

In director Bob Swaim's R-rated, plot-twisting, romantic psychological sex-filled thriller - the neo-noirish mystery plot was about murder, greed, double-crossing deception, surprise deaths and betrayal. The film's title referred to the name of a yacht anchored off the Hamptons, and to the deceptive nature of many of the characters. On a budget of $12 million, the film barely recouped its expenses with domestic revenue of $15.8 million.

In the script by Richard D. Wolf, the main story centered around an heiress and the circumstances swirling around her in Southhampton, Long Island, NY due to her estate/trust wealth of $300 million. The sophisticated plot about dangerous circumstances surrounding a trusting heiress who began to suspect that she was being set up by her playboy suitor to be killed, was similar to the plot of Hitchcock's Suspicion (1941). There were also shades of William Wyler's The Heiress (1949) about a shrewd and manipulative male suitor who was after the title character's ("Olivia" de Haviland) money.

There were notable bombshell twists in the film's final one-third, including the deaths of all three co-conspirators who had plotted together for a long time to murder the wealthy heiress. The film's tagline hinted at the plot: "An heiress. A hustler. A set-up. A murder. MASQUERADE - It's not a game anymore."

• the film's main protagonist was introduced: Olivia Lawrence (Meg Tilly) - a wealthy, naive, shy, vulnerable and dreamy Hampton heiress, with an acquired estate of $200 million dollars; Olivia had recently been orphaned following the death of her mother a few months earlier
• Olivia was forced to live with her spiteful 'guardian' - a scheming, alcoholic and despicable stepfather Tony Gateworth (John Glover), who was a dissolute Atlantic City gambler with tremendous casino debts; the family's NYC attorney Harland Fitzgerald (Bernie McInerney) explained how Gateworth had been granted access to all of the Lawrence's eight properties in the will of Olivia's mother, and received a yearly stipend of about $1 million each year
• in the Southhampton mansion, Tony was accompanied by his new live-in girlfriend-companion Anne Briscoe (Dana Delany)
• after recently graduating from college, Olivia met two possible suitors on her return home:
  • Tim Whalen (Rob Lowe, just before the actor was involved in a sex tape scandal) - a playboyish, attractive, but callow sailing instructor and racing yacht skipper/captain
  • Mike McGill (Doug Savant), a grown-up children friend, now an amiable Hampton Shores police officer who since he was 12 years old had a romantic interest in Olivia and dreamed of marrying her one day

Three Main Male Characters in the Plot
Tim Whalen (Rob Lowe) - Sailing Instructor and Captain	Mike McGill (Doug Savant) - Hampton Shores Police Officer	Tony Gateworth (John Glover) - Olivia's Abusive Stepfather

• while becoming acquainted with Olivia, Tim was also involved with another lover on the side: Brooke Morrison (TV's Sex and the City's Kim Cattrall) - the sex-crazed, bored and lustful wife of Tim's wealthy boss Granger Morrison (Brian Davies), who owned a racing sailboat Obsession captained by Tim
• after a scene of love-making between Brooke and Tim in the film's most-quoted sequence, she rolled over onto her back as they began to converse: (Brooke: "This is the first summer I've looked forward to in years." Tim: "He really trusts me." Brooke: "Who?" Tim: "Your husband." Brooke: "C.G. (laughs) Thank god. (He sat up) It's not that painful, is it?" Tim: "No, that's the problem. It feels too good to stop." Brooke: (She grabbed him and kissed him from behind) "We could always give it a try. Maybe we should stop this. Or maybe this")

Tim's Affair with Brooke - His Gift of a Birthday Present

• Tim left their bed and stood there bare-assed as he offered to give her a birthday present - a pair of black-lace panties, about which she asked: (Tim: "You want your birthday present, don't you?" Brooke: "You remembered. That's more than my husband did. Do you want me to put these on?" Tim: "I can't bite 'em off if you don't.")
• after Olivia and Tim met at an evening party and talked about sailing, they went sailing later in the week on the Masquerade, the name of the boat owned by her deceased father, the two began to date and fall in love
• the storyline became quite complicated due to conspiratorial plans or plots to murder Olivia, to acquire her fortune, depending on which male was involved
• although Olivia believed that Tim wasn't interested in her money, Gateworth tried to abusively convince her that Tim was a gold-digger and pressured her to end their relationship
• ironically, Tim and Gateworth were partnered and plotting together to steal Olivia's inheritance; they met together in a lobster-house diner, where Gateworth pressured Tim to not back out of their conspiracy, or otherwise Tim's dubious past would be revealed; Tim stated he could convince Olivia of his hatred of Gateworth and gain her confidence so that he could continue to assuredly court her and soon marry her

Passionate Love-Making Between Olivia and Tim Whalen

• on the weekend, Olivia and Tim experienced a night of passionate sex in her mansion when Gateworth was scheduled to be away; in the execution of their plot, when the drunken, weapon-wielding Gateworth burst into their bedroom just after they had made love, Tim engaged in a brief struggle with Gateworth, and double-crossed him by not just scaring him away, but by shooting him to death with his own gun; it was a ploy for Tim to gain Olivia's confidence in him [Note: Or was his motive to hide his own guilty plans, and to guarantee a non-divided share of Olivia's wealth?]
• Olivia volunteered to cover up Tim's role by claiming she killed the drunken Gateworth in self-defense with his gun - believing he was a burglar-rapist, and hoping it would be ruled a "justifiable homicide"
• Tim's unsuspecting lover Brooke substantiated Tim's fake alibi that she was with him from 11:30 pm onward at the time of the murder (to fool her before she awakened, he had reset her bedroom alarm clock without her knowing); shortly later, Tim broke up with Brooke, but still had the proper alibi
• at the crime scene, investigating cop Mike had found two wine-glasses by the bedside - evidence that could incriminate Tim, but he hid it from detectives (due to his apparent love for Olivia), while suspecting that Tim had killed Gateworth
• meanwhile, Gateworth's girlfriend Anne was asking lots of reckless questions, and becoming overly suspicious about Olivia's boyfriend Tim (she also knew, through a friend, of Tim's unlikely meeting in the lobster house-diner with Gateworth, just before Gateworth's death)
• after Tim confessed to Olivia that he had an affair with Brooke, and that his past was a bit shady, including bouncing checks (and 30-day jail time), he convinced Olivia that he was open and truthful with her - and the couple married; following the wedding, family attorney Harland Fitzgerald suggested that the couple create new wills (and Olivia insisted on a joint will for the two of them)
• shortly after Anne told officer Mike McGill about her knowledge of Tim's and Gateworth's get-together at a restaurant, she was found hanged above her bathtub - with a typed and unsigned suicide note (she was presumably killed by McGill, to be blamed on Tim); McGill asked for an autopsy
• officer Mike McGill was now revealed to be treacherous and implicated with Tim in a murderous conspiracy to kill the pregnant Olivia (the spiteful McGill admitted: "I spent a whole year of my life setting this thing up"); he wanted to stage a deadly car accident on a curvy road into a tree (on an oiled-up surface), but Tim balked at the idea of murdering Olivia, now that she was pregnant; McGill applied pressure by threatening to reveal the wine-glasses evidence he had concealed; Tim went ahead with the plan, but was able to maneuver through the slick patch without incident
• a photo on a bulletin board in McGill's marina maintenance office showed the threesome (Gateworth, McGill, and Tim) had been associated with each other (through sailing) for many years - and had probably always been plotting to separate Olivia Lawrence from her money; it was very probable that McGill and Tim were bi-sexual lovers, but when Tim was seduced away by Olivia, Tim's fury about unrequited love (from both Olivia and Tim) caused him to carry through on a new plan to kill Olivia by sabotaging their boat
• Mike's next deadly plan was to blow up the Masquerade and kill Olivia, by using the excuse that the explosion was due to a rat chewing through the propane line; to acquire Tim's reluctant cooperation, Mike again threatened to charge and frame Tim with the murder of Anne Brisco
• Tim was planning to sail for Palm Beach, Florida on Masquerade with Olivia, but was set to leave a few days earlier than he had told McGill, to save Olivia from the planned explosion; on the day of their sailing departure, Tim lost his life trying to warn Olivia, fearing that she was on the boat; he raced onto the yacht before she arrived and turned on the propane gas, but then inadvertently flicked a switch that triggered McGill's rigged gas-line explosion
• while distraught in the marina's maintenance office of Mike's father Tommy McGill (Barton Heyman), Olivia saw the photo of the threesome, and figured out the conspiracy against her by the trio; she confronted Mike McGill who entered, and as they struggled, she pushed him out of the office window to his death below

Tim's Death in Masquerade Explosion

Mike McGill's Death - Pushed Out a Window by Olivia

• all along, Olivia didn't know whether to trust Tim - did he love her truly, or had he courted and married her only for her money?
• by the film's conclusion, although Olivia had thought that Tim had betrayed her, she learned otherwise that his love wasn't a masquerade; at Tim's funeral, she discovered - to her relief - from family attorney Theodore Cantrell (Pirie MacDonald) that her dead husband had asked to be removed from her will two weeks earlier - proving his true love for her and that he had sacrificed himself for her: "He made me swear that I wouldn't tell you, but now with what's come out, you have to know. I think somehow he wanted to have all temptations removed. I tried to dissuade him, told him it was against your wishes, but he was adamant. He wanted nothing from you. He loved you, Olivia. However it started, he came to love you."