After bouncing around in supporting roles for years, Michael Caine became a star with the 1966 film Alfie, which cast him as a ladykilling cad infected with the spirit of swinging London. Directed by Lewis Gilbert from Bill Naughton's screenplay adaptation of his own play, the film initially seems infected with the same spirit, but that dissipates as Caine makes a rake's progress from carefree bachelorhood to a premature midlife crisis. Heavy-handed in its moralizing—there must be some middle ground between living a straight-and-narrow life and hiring a ghoulish Denholm Elliott to perform a house-call abortion—Alfie nonetheless captures the age as neatly as a stack of Zombies 45s. Caine does most of the heavy lifting. Turning his never-all-that-handsome face directly to the camera, he somehow remains charming even as he explains his devious ways. It's tricky to play a seducer, and trickier still to turn those powers of seduction on an audience that's already in on the scam.
Directed by Charles Shyer (best known for the 1991 Father Of The Bride remake and its sequel), the 2004 remake of Alfie recasts the part using Jude Law, a fine actor who nonetheless never makes the role his own. That's partly because he looks like a natural-born ladies' man, which makes his seductions seem like less of a trick. Mostly, however, he just looks like a man out of time: Taking on such an iconic role, Law can't help but seem like an echo of Caine. Seeing a character so linked to the free-spirited '60s scootering around contemporary New York in pinstripe suits, it's easy to wonder whether the projectionist has accidentally started an Austin Powers film.
A limo driver looking to start his own business with his best pal Omar Epps, Law spends his nights flitting from place to place and woman to woman, most often settling in at the home of semi-regular girlfriend Marisa Tomei and her young son (who, in one of the many instances of the story getting softened in translation, belongs not to Law, but to a previous boyfriend). Caught cheating, Law tells Tomei goodbye and spins into an ongoing crisis that involves bedding Epps' girlfriend (Nia Long), an unstable party girl (Sienna Miller), and an older woman (Susan Sarandon). His worries intensify with each conquest, but the film never finds the depth to match. Distracted by every opportunity to show off some graceful camerawork, Shyer puts the human element in the back seat. Caine played Alfie as an incorrigible S.O.B. who at least made for good company. Law makes him a delicate boy with self-control problems who can't stop talking, and his charm runs out long before the film ends. Law chases skirts down one dead end after another, but Alfie—with its flash, its dazzle, its reliance on dead-on-arrival dialogue, and its need to soften the blows—keeps a respectful distance from what it's all about.