While Flanagan has high personal aspirations, Doug is leery of the notion of starting their own bar together. Doug intends to call his Cocktails & Dreams.
Eventually, Brian and Doug's act becomes popular and they end up working at a trendy nightclub catering to New York's wealthy and elite; the type of establishment where yuppies spout poetry from the top of the rafters for all patrons to hear. As their popularity rises, Brian becomes the focus of attention from a sultry brunette named Coral (Gina Gershon). Quickly, they elevate their friendship into a wild sexual relationship. Glib Doug doubts that any woman would be so attracted to such a "loser" as Flanagan and during a free throw shooting conversation, Doug bets him Coral will leave him by week's end; essentially doubting there is anything special about the seemingly perfect relationship shared between the two. Unbeknownst to Brian, Doug lies to Coral about secrets being shared by Brian about her, and secures his bet by bedding the hot brunette. Brian is very upset and immediately quits his job, essentially ending his informal partnership with the older, wiser, and now relaxed, Doug.
Flanagan, taking advice from his former girlfriend, takes a job in Jamaica as a bartender to raise money for his own place; far away from the hustle, bustle and poetic yuppies of Manhattan. He finds a romantic partner in Jordan Mooney (Elisabeth Shue). Jordan is an aspiring artist from New York who, for now, works as a waitress. She and Brian fall for each other. Doug shows up in Jamaica, now married to Kerry, a wealthy woman (Kelly Lynch). He quickly asserts himself and bets Brian to sleep with a barfly named Bonnie (Lisa Banes), a wealthy older woman. Jordan catches Brian in the act and is devastated. She takes an overnight plane home to New York City.
Brian also returns to New York, with the athletic Bonnie, with the understanding that he will be placed high up in her company due to their romantic attachment. Brian becomes impatient as the payoff is too slow. They have a blowup during an art exhibition where Brian gets into a fight with the unshaven artist. As they cut ties, Brian, displaying wisdom one can only assume has been gleaned from his former mentor, states: "All things end badly. Otherwise they wouldn't end!"
Brian then seeks out Jordan. Much to his surprise, Brian learns that she is pregnant with his child. He embarks on a journey to win over the independent Jordan and prove to her that, despite being just a bartender, he would make a worthy father. While pursuing Jordan, Brian also learns that her family is very wealthy, and he goes to her parents' Park Avenue penthouse to speak with Jordan. Unhappy with the situation, Jordan's father, Richard (Laurence Luckinbill) attempts to buy him off, without success.
During this time in Brian's lackluster life, he meets up with his old mentor, the aging Doug. Despite the outward appearance that Doug is living the good life, Doug confides in Brian the end is near for him as his wife's money is nearly gone; lost in the stock market. Doug is despondent about his situation, unwilling to let on to his new bride about the precarious monetary position they are in. Brian is completely shocked by the news; then Doug kills himself by using a broken glass to cut his wrists.
Now reeling from the misfortune of the stiff-arm from Jordan, and losing his best friend to suicide, he goes to Jordan's father's home (where Jordan is staying) and begs her forgiveness. He further promises to take good care of her and their child. Brian has a brief scuffle with Jordan's father's staff, then takes the willing Jordan by the hand and heads for the door. They leave together, finally, as a couple and future mother and father. Using the advice of the other (better) mentor in his life, his Uncle Pat Ron Dean, Brian is able finally meet his life's goal by opening a bar called "Flanagan's Cocktails & Dreams". They have their wedding reception at the smoky bar while Jordan is visibly pregnant. Just before the credits, Jordan reveals she is pregnant with twins.
Despite the film's success at the box office, the film won two Golden Raspberry Awards for Worst Picture and Worst Screenplay and Tom Cruise was nominated as Worst Actor.
|1989||Australian ARIA Albums Chart||1|