"The Apartment" (dir. Billy Wilder)
Jack Lemmon and Shirley MacLaine share some of cinema's most crackling onscreen chemistry in Billy Wilder's 1960 romantic comedy about lonesome corporate serf C.C. Baxter (Lemmon) and the elevator operator of his affections Fran Kubelik (MacLaine) in an Upper West Side insurance agency. The movie unfolds throughout the holiday season but ends on New Year's Eve when this much-thwarted courtship is sealed by MacLaine's classic quip: "Shut up and deal."
"The Hudsucker Proxy" (dir. Joel and Ethan Coen)
The far-out final act of the Coens' 1994 Capraesque screwball comedy starring Tim Robbins as a quixotic mail room employee entangled in a stock scheme culminates on a delirious New Year's Eve. In an homage-packed scene riffing on everything from Harold Lloyd to Hitchcock's "North by Northwest," Robbins' Norville Barnes looms perilously on a high rise clock that reads "The Future Is Now." Ace performances from Jennifer Jason Leigh and Paul Newman round out this light Coen effort in which the Brothers take on the most dastardly of all worlds: business.
"Strange Days" (dir. Kathryn Bigelow)
Though Bigelow is now known best for her politically charged prestige pictures "The Hurt Locker" and "Zero Dark Thirty," this 1995 genre oddity starring Ralph Fiennes, Angela Bassett and Juliette Lewis (all in their heyday) predicts a very dark future at the tail-end of the millennium. This dystopian thriller set in 1999 Los Angeles amid a conspiracy-soaked milieu of surveillance, police corruption, virtual reality and existential paranoia turned out to be far more prescient than we could have imagined. It's also wildly cinematic.
"Sunset Boulevard" (dir. Billy Wilder)
Make it a Wilder double feature this New Year's with the 1950 doom-laden noir "Sunset Boulevard," the great director's ageless portrait of a greed-ravaged Hollywood haunted by washed-up movie stars, two-bit screenwriters and crooked cops. In a New Year's-set party scene, withering silent film actress Norma Desmond (Gloria Swanson) heaps luxury and seriously desperate affections upon Hollywood hack and protege Joe Gillis (William Holden), a nobody who wants to be a somebody in a thankless industry. Their demented relationship/romance/folie-a-deux or whatever you want to call it climaxes in a wicked, violent finale recently quoted on AMC's "Mad Men" -- the perfect swan song for another year.
"When Harry Met Sally" (dir. Rob Reiner)
Only a heart of stone could resist Reiner's timeless 1989 "Annie Hall" knockoff about two neurotic New Yorkers who spend a decade wondering if a man and a woman can ever, truly, just be friends. It's as much screenwriter Nora Ephron's film as it is Reiner's, with compulsively quotable dialogue and one iconic scene after the next. While Billy Crystal is adorable as death-obsessed nebbish Harry, Meg Ryan's kooky, stubborn Sally steals the show, clinching her fate as the go-to rom com queen of the 90s. And you simply have to love her takedown of the ridiculous lyrics to "Auld Lang Syne." What the hell is that song even about, anyway?