First there is Siddie (Millicent Martin), a married woman looking for amusement from Alfie, which is fine with him until she tries to connect him with her fuddy-duddy husband. Alfie also regularly visits Gilda (Julie Foster), a beautiful blonde bearing his child. He can't convince her to get an abortion, and she changes her mind about adoption. Sensing an opportunity, her formerly spurned would-be boyfriend Humphrey (Graham Stark) makes another attempt at her, and outmaneuvers the feckless Alfie.
Alfie's inevitable rebound is postponed by a brush with tuberculosis, diagnosed by Eleanor Bron. She sends him to a country convalescence home, where he bonds with family man Harry (Alfie Bass), a somewhat older man whose condition is worse than his. Harry is visited each week by his wife Lily (Vivien Merchant).
Bad boy that he is, Alfie has a one-day tryst with Lily. Then he picks up Annie (Jane Asher), who is fleeing a failed relationship in another city. Alfie mistreats lovely Annie and is surprised when she packs up and leaves him.
The now empty apartment comes in handy when Lily shows up pregnant from her momentary romance with Alfie. He pays an abortionist, Denholm Elliott, to induce premature labor, leaving him with a small but ghastly reminder of his poor behavior.
Meanwhile, Alfie's romance with rich maneater Ruby (Shelley Winters) turns sour, leaving Alfie to wonder what it's all about, as asked by the lyrics of the film's theme song.
How others will see it. Alfie is based on a short-lived London play by Bill Naughton. Naughton also wrote the screenplay. The movie was a critical success, and also did banner box office, ending up as #13 for the year in the U.S. on a fairly low budget. It was nominated for five Oscars, three in major categories (Best Picture, Best Actor, Best Adapted Screenplay), but took home no trophies, mostly due to A Man for All Seasons, which won six Oscars that year.
Considering the film's 1966 reception, and its significance in making Michael Caine an A-list moviestar, it is interesting that, at imdb.com at least, Alfie has only a so-so 10K user votes and a less-than-stellar user rating of 7.1 (out of 10). Certainly, there are many viewers, both male and female, who dislike the character of Alfie, as Exhibit A in the category of skirt-chasing cad. It probably doesn't help that the 2004 remake, starring Jude Law, was a flop.
How I felt about it. Alfie is a selfish hedonist. But in his mind, at least, he's not such a bad guy. He openly tells his girlfriends that he will come home whenever he pleases and will never commit. He appears to love Malcolm, his illegitimate son, and he visits Harry at the tuberculosis ward. But that won't keep him from breaking up with Malcolm's mother, or impregnating Harry's wife.
Alfie's character, or lack thereof, is contrasted with Humphrey, who wants to marry Gilda even though she is raising someone else's son. Humphrey will devote himself entirely to Gilda and little Malcolm, and he wins the girl.
Ultimately, even Alfie recognizes that his philosophy on romance has been a failure. Ruby demonstrates that a wealthy woman with options will make a sucker out of him, just desserts for a man who has played the field for so long. His impetuous demands have run off Annie, Siddie shows little interest in him, and all he has left is man's best friend, a street dog.
From the perspective of psychology's Transactional Analysis, Alfie has been living as a Child, pleasing his whims, instead of acting as an Adult, preparing for the future. It is actually hard for a man to live as a Child. Most men would have promptly committed to Gilda or Annie, each more submissive and beautiful than the other. But for Alfie, he figures that his charm and cunning will always find the greener grass in the next pasture.
The film spawned three different versions of the Burt Bacharach / Hal David theme song, respectively by Dionne Warwick, Cher, and Cilla Black. The first two charted in America, the third in the U.K. Warwick had the best voice and eventually, the biggest hit, #5 on the Billboard Rhythm & Blues chart.