Unforgettables: Cinematic Milestones #1 – Outrageous Fortune (1987)

Outrageous Fortune: Midler and Long butt heads and build friendships in a buddy comedy classic

NOTE: This feature originally appeared in the January 7, 2022 edition of the Seattle Gay News. It is reprinted here by permission of the publisher Angela Craigin.

I remember my first viewing of director Arthur Hiller and screenwriter Leslie Dixon’s 1987 comedy Outrageous Fortune as if it were yesterday. This happened at a Spokane drive-in. I was a month away from turning 13, and my little sister was barely four-years-old. Our family trips to the movies were understandably growing fewer and further between now that she was part of our clan, so this outing was something of a special occasion.

I loved the film. I was now old enough to understand most of the double and triple entendre not-so-subtly concealed within Dixon’s script. Even more, I was fascinated by the blossoming female friendship in the Hitchcockian mistaken-identity scenario central to Hiller and Dixon’s comedy.

Outrageous Fortune spoke to me. I even saw it an additional three times in the theater, even though technically I was not old enough to do so. Granted, by the time the film made its way to second-run theaters, it’s not like the teenage ticket takers were all that interested in checking my I.D., by that age I was already 6’2” and some would say moderately imposing.

Hiller and Dixon’s film was released 35 years ago this month. Starring Bette Midler and Shelley Long, it’s one of a handful of 1980s hit comedies that’s managed to hold up over the decades. While certain aspects have undeniably aged poorly, there’s less of that here than is typical for films of this era. This is a wildly entertaining adventure with a giant heart. Better, it overflows with a number of genuine belly laughs.

The plot is pure Hollywood suspense-thriller hokum: Struggling actresses Lauren (Long) and Sandy (Midler) loathe one another on sight. The former is a prima donna from a wealthy family. The latter is a street-smart broad with a potty mouth who can talk her way out of anything. They’re in an acting class taught by stern Russian taskmaster Stanislav Korzenowski (Robert Prosky). Unbeknownst to either of them, the women are also dating the same man, kindly primary school teacher Michael (Peter Coyote).

Needless to say, he’s not who he says he is. After he dies in an apparent explosion, Lauren and Sandy discover they’ve been inadvertently dating an ex-CIA agent who has recently stolen a top-secret poison with the intent to sell it to the highest bidder. Not that the women are initially privy to any of that information. They only know Michael isn’t dead — the burned body just wasn’t big enough where it mattered most — and that they are determined to find him, mostly so they can find out which of them he has feelings for and which he’s been using purely for sex.

It’s hard not to think that films like Susanna Fogel’s 2018 delight The Spy Who Dumped Me owe a massive debt of gratitude to Outrageous Fortune, most notably Dixon’s gloriously silly yet shrewdly intelligent screenplay. In lesser hands, this could have been a slovenly mess. But with writing this honest, and with Hiller directing with the same comedic precision he brought to his male-dominated buddy comedies The In-Laws and Silver Streak, the overall result is quietly groundbreaking.

Female friendships born out of animosity and distrust aren’t anything new, cinematically speaking, of course. But in the context of a motion picture like this one? Where the women get to be every bit as uncouth as men? Where they also get to dodge bullets, steal suitcases filled with money, and otherwise selflessly save the day? Examples on that front are rare, the most obvious being Louis Malle’s scandalously entertaining 1965 Western Viva Maria! with Brigitte Bardot and Jeanne Moreau, made over two decades before this Midler/Long collaboration ever saw the light of day.

Are there speedbumps? Certainly. Like many ‘80s comedies, certain gags haven’t aged well, particularly a brief sequence where the ladies get assistance from a tough-talking Black cab driver and head into Harlem to learn more about Michael. What was only somewhat regrettable back in 1987 is far more uncomfortable now.

But there are so many more instances where Outrageous Fortune is proudly ahead of its time. There’s a lovely joke about an actor being forced to hide being Gay that’s deftly underplayed by Long and a scene-stealing Christopher McDonald in one of his earliest roles. An even better bit a few beats later involves Korzenowski trying to teach his acting class the best way to “play dead.” Midler melts hearts into oozing bits of disquieting gelatin as Sandy is forced to react when her teacher maliciously ridicules her for not knowing Shakespeare’s Hamlet.

Midler was on an incredible streak for Touchstone Pictures at this point in her career. Her small role in Down and Out in Beverly Hills had people revving to see more of her. They got their wish just a few months later with the release of Ruthless People, in which the Divine Miss M reasserted herself not so much as a major talent but as a bona fide force of nature. She followed this up with Big Business with Lily Tomlin and the classic five-tissue weepie Beaches with Barbara Hershey, the latter concluding an extraordinary five-picture run.

Long was top-billed here, in large part due to her Emmy-winning fame from playing Diane Chambers on Cheers. She’d also come off a pair of comedic hits, 1982’s Night Shift with Henry Winkler and Michael Keaton, and 1986’s The Money Pit with Tom Hanks. She’d have a few more high-profile film roles after this one, another 1987 release, Hello Again, and the minor cult favorite Troop Beverly Hills in 1989. But Outrageous Fortune is the picture that utilized her talents the best, and it’s a shame she’s never found another role or motion picture its equal.

I think what ultimately makes this one so special is its rather clever and unobtrusively knowing examination of identity. Whether it’s a magnificent George Carlin popping up in the third act as an alcoholic New Mexico guide who knows a thing or two about lasting friendships, or the ways Midler and Long have a field day playing against traditional gender roles and stereotypes, there is precious little that follows typical genre conventions.

My favorite moment comes at about the midpoint of the story. Lauren and Sandy have done the impossible and tracked Michael down. About to confront him and find out the information they think they want to know, the pair put their competition aside as they help one another primp and pass on heartfelt words of encouragement before making their presence known.

Even though it remains unspoken, it is in these precious few seconds before they get an answer to a question they erroneously believed they were waiting for where the women realize they’ve somehow, someway become friends. From that point everything changes. Their bickering becomes more supportive. Their differences only augment the other’s strengths. Lauren and Sandy come to understand they work better together than they ever did apart, and they don’t need a man to care for or tell them otherwise, let alone save the day. They can handle that on their own.

Now celebrating its 35th anniversary, “Outrageous Fortune” is available on DVD and to purchase digitally on multiple platforms.