FromCapotetoPunch Drunk Love,Philip Seymour Hoffmanproved that he had limitless range when it came to the scope and breadth of the characters he plays. Maybe his most emotional role of all is in a film that you might have skipped over back in 1999 when he played a gay drag queen named Rusty oppositeRobert De NiroinFlawless. Though the film was not one of Hoffman’s most widely seen projects, his heart-rendering story of a flamboyant drag queen awaiting gender reassignment surgery is one of the most poignant roles of his career.Flawlesswas his first film coming off the heels of two very successful box office hitsBoogie Nightsand a smaller role inThe Big Lebowski,and just beforeThe Talented Mr. RipleyandMagnolia,so it flew under the radar a little bit. Of course, we are talking about a cisgender male actor playing a trans woman. Unfortunately, this was the norm in the 90s, with other films likeThe Crying Gamecasting cis men to play trans women. Trans representation has come a long way since, and the days of cis actors playing trans characters are mostly behind us. However,Flawlessstill has its merits in its depiction of friendship, sexuality, and people’s different approaches to expressing their gender.

Philip Seymour Hoffman and Robert De Niro Are Polar Opposites

Hoffman’s character, Rusty, is a flamboyant, intelligent trans woman who wants to have gender reassignment surgery, and who loves to have friends over for some piano-playing sing-along sessions.Robert De Niro’s turn as Walt Koontz is the complete opposite. Koontz is a retired security guard who spends his time bowling, playing poker with the guys, dancing the tango, and reliving his glory days when he thwarted an attempted bank robbery some 12 years prior. His apartment is littered with bowling trophies and a letter of recognition from New York City Mayor, Ed Koch, for his heroic deed. The two live across the courtyard from each other in a run-down New York apartment building, where the two can be heard arguing over the noise coming from Rusty’s apartment on a daily basis. These are two people with completely different views on what it is to be a man, sexuality, and socially acceptable gender roles. So much so, that it is more than fair to say that Koontz is a bona fide homophobe and transphobe who wants nothing to do with Rusty and what he considers to be a perverse lifestyle.

Rusty and Walt Forge an Unlikely Friendship

When “man’s man” Koontz suffers a debilitating stroke amidst a shootout in the building that leaves him partially paralyzed, his physical therapist recommends taking singing lessons to improve his speech. Well, wouldn’t you know that his neighbor and nemesis, Rusty, is qualified to give those tutorials, and Koontz begrudgingly approaches Rusty requesting lessons. After some posturing and back-and-forth bickering between the two, as they voice their opinions about how the other’s lifestyle is inappropriate and lacking, the two slowly start to learn that there is more common ground between them than originally thought. The two begin to stop seeing what’s on the surface and peel back the layers of why they are who they are and share mutual struggles over difficult upbringings, loneliness, and a basic desire to want to have value and meaning in their lives. Hoffman is on target a trans woman who is struggling with bias and contempt on a daily basis but talks a big game in order to protect herself and hide her insecurities about struggling to decipher why she was born into such a difficult predicament.

‘Flawless’ Explores People Connecting on a Basic, Human Level

Hoffman’s sassiness and flamboyancy are an emotional shield that protects Rusty from the prejudices and inherent biases of a society that doesn’t understand how a trans woman won’t accept society’s ideas of what men should look and act like. De Niro’s Koontz is supposed to serve as a template of a kind of toxic masculinity that carries a preconceived disdain for the choices that Rusty has made with her life. But at the heart of the relationship, they come to find out that they are both just trying to find purpose and meaning. Over the course of their time together singing, both of them begin to let down the force fields they have constructed around themselves and start to bond over the things that make them more than just neighbors. We find that beneath the wigs and layers of make-up, Hoffman’s Rusty is a lost soul who is secretly stashing away money in order to undergo gender reassignment surgery. It’s a moving scene when Rusty and Koontz drop all the pretenses that have shaped their relationship up to that point and speak to one another as equals. As they are forced to let go of their defenses, they see that they’re not all that different on the inside, and what separates them are nothing more than social constructs that we can choose whether or not to buy into.

Walt and Rusty Are Forever Tied to Each Other

When a local loan shark and his thugs come calling on Rusty toting guns after finding out that she’s been holding out on him and spending what money she does have on gender reassignment, Koontz isn’t having it. The physically challenged former hero security guard struggles to come to Rusty’s defense but still manages to kill the loan shark and save Rusty’s life. During the scuffle, Koontz takes a bullet to the shoulder and has to be taken by ambulance from the scene. In a moment where we see that the relationship between the two has come full circle, the once dismissive and rigid Koontz tells the EMT at the scene that Rusty can ride with him to the hospital as she is a family member. Once inside, Hoffman dazzles one final time as Rusty presents a stack of cash and hands it over to the driver of the ambulance demanding he step on the gas and get her friend to the hospital as soon as possible where only their best surgeon is allowed to operate on Walt. (Again, this was 1999. In today’s world, Rusty would keep the money to finally get her gender reassignment surgery, as she should.) It’s a remarkable portrayal for Hoffman who made a career out of playing eccentrics and misfits. Hoffman’s Rusty inFlawlessis yet another showcase of the great, late actor’s talent.

Robert de Niro and Philip Seymour Hoffman in Flawless

Philip Seymour Hoffman Robert De Niro Flawless

Philip Seymour Hoffman as Rusty in Flawless (1999)

Philip Seymour Hoffman as Rusty in Flawless