The 1980s films of Michael Caine: Dressed To Kill

We continue our exploration of Sir Michael Caine’s films of the 1980s with a classic that hasn’t aged very well, Dressed To Kill.

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Michael Caine showed no sign of slowing down as he entered his third decade as a leading man. The 1980s would see him win his first Academy Award (Hannah And Her Sisters), tackle new genres such as horror (The Hand) and shark-based revenge movie (Jaws: The Revenge) while continuing to work with interesting new auteurs like Brian De Palma (Dressed To Kill) as well as old friends from classic Hollywood such as John Huston (Escape To Victory). 

Film by film, we’ll be taking a look at Caine’s 1980s filmography to see what hidden gems we can unearth alongside the more familiar classics…

Big spoilers for Dressed To Kill, and Psycho, lay ahead…

Directed by: Brian De Palma (Carrie, Scarface, Body Double, The Untouchables, Mission: Impossible)

Tagline: Brian De Palma, Master of the Macabre, invites you to a showing of the latest fashion…in murder.

Other Featured Geezers: Angie Dickinson as Kate Miller, Nancy Allen as Liz Blake, Keith Gordon as Peter Miller, Dennis Franz as Detective Marino, David Margulies as Dr Levy. 

What’s it all about, Alfie?: Kate Miller (Angie Dickinson) is a sexually frustrated housewife who, in-between appointments with her psychiatrist Dr Robert Elliott (Michael Caine) and discussions about cake based Napoleonic myths with her nerdy son Peter (Keith Gordon), is looking for a bit of extramarital excitement. Tragically this ultimately leads her straight into the blade of a mysterious razor wielding blonde (who looks suspiciously like Michael Caine in a wig and dark glasses).

In the wrong place at the wrong time, high class call girl Liz (Nancy Allen) also becomes embroiled in the aftermath of Kate’s murder, falling under the suspicion of sleazy Detective Marino (the always reliably sleazy Dennis Franz), and teams up with Peter to find out who killed his mother.

Caine-ness: Caine is first billed as psychiatrist Dr Robert Elliott, whom we first see around eight minutes in. He’s at his office which is subtly yet tastefully decorated with a framed print of a bisected Battenberg (at least that’s what I’m interpreting it as. Although, analysing myself, this may simply be because it’s tea-time and I’ve just watched Bake Off).

Dr Elliott, much like Sting, is an Englishman in New York, and Caine gives a subdued, understated performance as the calmly mannered shrink with a dark secret. He’s softly spoken and affable but he’s certainly no Frasier Crane. I have significant doubts about his professionalism as a medical practitioner (even if you overlook the murdering, which definitely is a pretty major violation of the Hippocratic oath).

In his session with Kate after she says, “Do you find me attractive,” he replies, “Of course”, and to her follow up of “Do you want to sleep with me?” he casually responds with “Yes” but he won’t “Because I love my wife”. I appreciate his honesty, but I’m not sure this is encouraging the right patient/doctor relationship.

He does dabble in professionalism occasionally though, as he refuses to give up patient/doctor confidentiality when being interviewed by Detective Marino (Dennis Franz) and when Marino asks if the murderer could have been one of his “weirdo” clients, Elliott, clearly taking offence at Marino’s insensitive use of language, responds with; “The term we use, Detective, is not weirdo, but a person suffering from emotional dysfunction and a problem of mal-adaption”. 

He’s also a canny businessman as, when he and Peter are both waiting outside the office to be interviewed by Marino about Kate’s murder, he gives Kate’s grieving son his business card and tells him to call him. I don’t blame him, you’ve got to take work wherever you can get it, Elliott’s a real go-getting man of the 80s.

Read more: The 1980s films of Michael Caine: The Island

His suspicious bedside manner should have acted as a red flag to Kate because Dr Robert Elliott, unlike Sting (as far as I know), has that aforementioned dark secret. He is living with a split personality of a murderous woman called Bobbi, and he occasionally dolls himself up with a wig and a spot of lipstick and goes out killing – which we find out is due to him having serious unresolved issues with his gender identity.

Now is the time to deal with the troubling elephant in the room. This is not a sensitive or realistic depiction of a transgender person and it has rightly received criticism as part of the harmful trend in thrillers of making trans characters dangerous predators. It’s totally understandable why people would find this film offensive or upsetting.

For what it’s worth, I don’t think De Palma intended it as such, or was doing it with any malicious agenda, but simply, in a less informed era, he was naively doing a twist on Psycho without really thinking of the wider implications of this character. We do actually see a trans woman being interviewed on a show that Liz and Elliott are both watching. This woman used to work in the police force, and although only seen fleetingly, she seems normal and well-adjusted. So, there does seem to be some attempt by De Palma to ensure that the film doesn’t portray trans people entirely negatively, but it doesn’t make up for the character of Bobbi. 

Caine handles the role of Bobbi as delicately as possible. After Bobbi is shot, we see Caine gently weeping on the floor with his wig off and it genuinely evokes sympathy; this isn’t a character we are encouraged to hate, and Caine isn’t playing them simply as a raving lunatic. 

A significantly more trivial criticism is that I don’t believe that the film plays fairly with the twist that Elliott is Bobbi, because when Elliott listens to Bobbi’s answerphone messages, it’s very clearly not Michael Caine’s voice. Although, admittedly, since the film is so heavily indebted to Psycho, we do hear “mother’s” voice in that film when Norman Bates is just imagining it (before the audience knows that), so I assume Elliott is imagining these answer phone messages, too. Also, in some of the stalking sequences Bobbi is actually being played by the actress Susanna Clemm (who plays the policewoman) rather than Caine (which I think is cheating, I want more Caine in a wig).

According to IMDB when Caine’s agent, Swifty Lazar, saw the film, he said to Caine; “Michael, you must never do anything like this again, because as a woman you look like crap!”

One last thing to mention: when Detective Marino mentions to Elliott that the suspect is “a broad”, Caine gives the incredulous response of “a woman?” which nearly rivals Roger Moore’s delivery of the same line in Moonraker (under very different circumstances).

As the search for the mystery police station arsonist goes on, Marino hopes no one checks his bookshelf.

Caine-nections*: Caine has played bad guys before (complex anti-heroes like in Get Carter, The Eagle Has Landed and The Last Valley or comic antagonists like in Harry and Walter Go To New York) but this is the first time that he’s played this kind of proper thriller/slasher villain. 

*I’m only counting from Caine’s first starring role in Zulu onwards.

Best Non-Caine Actors: Angie Dickinson as Kate Miller is the first character that we properly see for an extended amount of time, and we see A lot of her (or her body double at least) and De Palma does the old Psycho trick of establishing her as the main character in the first third before shockingly killing her off.

Dickinson has since cited this as one of her favourite films, and she’s sympathetic and believable as the disaffected housewife. Kate is not a bad person, she cares a lot about her son Peter even though he’s a massive nerd who’s building some sort of supercomputer in his bedroom. However, one bad attribute that she does have is that, much like Ridley Scott, she’s okay with perpetuating myths about Napoleon (she says to Peter that Napoleon invented the Napoleon pastry because he “baked as a kind of relaxation” which is not true). 

Peter (Keith Gordon, who frequently popped up playing nerdy young men in the 80s but has since had a prolific career as a director) seems to be inspired by Brian De Palma’s own adolescence. As a young man, at his mother’s request, De Palma would follow his father and use recording equipment to try and catch him cheating. This fact may go some way to explaining why a lot of De Palma’s movies are as significantly messed up as they are. 

Peter’s investigative team up with Liz is charming; they have an easy chemistry, and it turns the latter third of the film into a slightly lighter adventure romp to stop it getting too bogged down in all the seedy murder stuff. De Palma specifically wrote the role of Liz Blake for his then-wife Nancy Allen and she’s great in this. There’s a sweetness and a sense of fun to her character. She’s definitely the idealised, and sanitised, Pretty Woman-esque version of a sex worker. Also, she lives above somewhere called First National Cookie. No one can be edgy if you live above somewhere with such a cute name. 

Best Featured Artwork Of An Embarrassed Ape Whose Just Been Caught About To Scratch His Bum

My Bleedin’ Thoughts: It’s in part sexist, in part transphobic, has a pretty generic plot, and is incredibly campy. However, Dressed to Kill is so consistently stylish, and made with such confident aplomb (De Palma really goes to town with his signature Split Diopter shots), that it becomes easy to get swept along and have a great time with this film while overlooking all the ickiness and flaws. 

De Palma films, at their best, are trashy delights, and this is one of his trashiest and most delightful. For those familiar with his filmography, you won’t be surprised that it starts with gratuitous extended female nudity as the camera pops in to see what Kate’s getting up to in the shower – all accompanied by Pino Donaggio’s incongruously romantic score.

There’s always a question of when De Palma is being satirical and when he’s being serious, of how much his films are criticisms of misogyny and violence and how much they are simply indulging in it. There’s certainly a lot of that to ponder in Dressed to Kill. De Palma is certainly of fan of having his cake and eating it (or maybe not cake – Napoleon pastries are a better analogy).

There are two extended sequences that are simply excellent pieces of filmmaking. Kate’s trip to the art gallery where she picks up her one-night stand (I assume this is the main reason people go to art galleries, surely it’s not for the art?) is dialogue free, and we are left with only Donaggio’s subtle score, and it’s a thoroughly captivating and gripping 10 minute sequence. Unlike Kate’s diary entries that she writes whilst admiring the paintings, which include the gems “nuts”, “eggnog” and “pick up turkey”.

But hey, I don’t judge – everyone gets different things out of art. If she looks admiringly at a portrait of a supine gorilla and thinks “hmm, I need to buy nuts”, there’s certainly nothing wrong with that.

Sadly, after a pleasant afternoon of hanky-panky back at his place, Kate goes to write her lover a note as she leaves, but finds a letter from his doctor saying that he has the unfortunate double whammy of syphilis and gonorrhoea. She understandably then leaves his apartment in a hurry, but before she can get out of the building realises that she’s forgotten her wedding ring (it’s no consolation that what she’s lost in jewellery she’s gained in an assortment of venereal diseases). This unfortunate timing is what then leads into her excellently orchestrated death scene.

It starts with the sinister vision of Bobbi’s face in the background of the shot, bathed in red, behind the fire door window. Then what follows are plenty of zoom ins, plenty of extreme close ups of eyes, and even images of the murder reflected in an elevator mirror. It’s all very tense and stylish. 

Trivia (courtesy of IMDB): Caine’s mate and former co-star Sean Connery was offered the role of Dr Elliott but had to turn it down. He would later go on to receive an Academy Award when working with De Palma on The Untouchables.

Breaking Bad and Better Call Saul’s Mark Margolis is uncredited as a mental patient.

When Kate Miller finds her one-night stand’s medical report telling him that he’s got venereal diseases it is dated 11/17/80. November 17th is the birthday of Martin Scorsese whom De Palma is close friends with. What a thoughtful gift for your pal!

Angie Dickinson has said the scene where she has it off in the back of a taxi was filmed on location, and several onlookers shouted, “Right on, Police Woman!” referring to her previous television role in Police Woman.

The Movie’s Secret Message: As mentioned, De Palma can be inscrutable, but I think, due to the power of my Media Studies A Level, I discovered the secret underlying message that De Palma was trying to convey spelt out in the corner of one of his shots;

Overall Thoughts: Dressed To Kill is artful trash of the highest order. It’s lots of fun if you can look past its shortcomings and it’s certainly a memorable villainous turn from Caine. This is certainly not a film for everyone, however, as it does have some problematic and upsetting elements (especially given the current cultural climate).

Rating: 4/5 Napoleon Pastries (which, Kate Miller, no, he DIDN’T invent)

Where You Can Watch This: Dressed To Kill is currently streaming on Amazon Prime, and available to rent or purchase from most streaming platforms or on Blu-ray.

Up Next: Oliver Stone, in his second jaunt in the director’s chair, gives Caine a hand (specifically a killer one) in The Hand.