(On DVD, January 2018) For late-twentieth century cinephiles such as myself, Jack Lemmon is first the eponymous Grumpy Old Man, or the miserable salesman of Glengarry Glenn Ross. But this late-career Lemmon is the last act in a long list of roles, and films such as The Apartment (alongside Some Like it Hot and The Odd Couple) do suggest that young Lemmon was the best Lemmon. He’s certainly charming in The Apartment, playing a young man who has struck a most unusual arrangement with his superiors at work: His apartment made available for dalliances, in exchange for professional advancement. The film does begin in firmly comic mode, as the protagonist juggles the schedules of four executives with his own desire to sleep, and then to court an elevator attendant played by Shirley MacLaine. The first half of The Apartment plays as a proto-Mad Men, capped off by a sequence in which Lemmon dons a dapper hat and strolls out like a true New York City professional with a bright future. The look at this slice of 1960 NYC living is terrific and if the film had stopped there, it would have been already worth a look. But there’s a lot of murk under the premise of the film and The Apartment soon heads deeper in those troubled waters, shifting from suggestive comedy to much bleaker romantic drama as the protagonist ends up in romantic conflict with one of his superiors, and then in even darker territory with a suicide attempt that changes everything. Director Billy Wilder had an illustrious career, and the way he shifts adeptly between three subgenres in a single film is a great example of what he could do with difficult material. The Apartment is still unsettling today—less so than upon its release, but it still defies sensibilities. The film’s second half is a great deal less fun than the first, but it does give much of the film’s enduring power.