Michael Caine (Dressed to Kill) Dressed to Kill

Michael Caine plays Dr. Robert Elliott, the Manhattan psychiatrist whose transsexual alter ego Bobbi commits the film's murders. The role was originally offered to Sean Connery, who was enthusiastic but declined because of previous commitments. Caine delivers what Film Stories called "a subdued, understated performance as the calmly mannered shrink with a dark secret." (filmstories)

Caine plays Elliott as composed and professional, making the reveal land harder

Elliott presents as the most reasonable person in the film -- he deflects Kate's advances with gentle firmness, cooperates cautiously with the police, visits Levy to warn about a dangerous patient. The performance works because Caine underplays it. There is no foreshadowing in his demeanor, no actorly winks at the twist. When the wig falls in beat 29, the audience has to reconcile Caine's measured psychiatrist with the razor-wielding blonde, and the gap between the two performances is what makes the reveal effective.

Caine handled Bobbi with restraint rather than camp

After the reveal, when Bobbi is shot by Betty Luce and the disguise comes off, Caine is seen gently weeping on the floor with his wig removed. Film Stories noted that the moment "genuinely evokes sympathy" and that Caine avoided playing the character "simply as a raving lunatic." The restraint is notable given the era -- most split-personality killers in 1980 were played as unhinged from the moment of exposure. (filmstories)

His agent's response became the film's best-known production anecdote

Caine's agent reportedly delivered the assessment that has followed the film through four decades of retelling:

"Michael, you must never do anything like this again, because as a woman you look like crap!" -- Michael Caine's agent, quoted in Film Stories

Caine was in his most productive period, making three to four films per year

Dressed to Kill sits in the middle of Caine's prolific early-1980s output. He made The Island and Dressed to Kill in 1980, followed by The Hand and Victory in 1981. This was the era when Caine famously took every role offered to him -- a strategy that produced both gems (Educating Rita, Hannah and Her Sisters) and acknowledged paycheck films. Dressed to Kill falls on the gem side: a technically demanding role in a filmmaker's most commercially successful work.