Wonderful upbeat performance from Frank Sinatra lifts this out of a misogynistic pit where women were either dumb, desperate to get married or passive-aggressive harridans. Bachelor playboy Alan (Frank Sinatra) has more women on a string than there is string. When younger brother Buddy (Tony Bill) moves in, Alan introduces him to the fun ways of the world, not expecting Buddy to be such an apt pupil.
Alan keeps main squeeze Connie (Barbara Rush) dangling while, pretending to have Hollywood connections, making hay with actress wannabe Peggy (Jill St John). He also keeps customer Mrs Eckman (Phyllis McGuire) sweet in transactional sex fashion and there’s no shortage of other women liable to appear out of the woodwork.

Meanwhile, his boss, apoplectic father Harry (Lee J. Cobb), goes around screaming at everyone, berating Alan for his lifestyle and moaning at harassed wife Sophie (Molly Picon). Most of the time it looks like it’s going to swerve into a more typical English farce with various women being hidden out of sight from various other woman or Harry or an equally apoplectic cuckolded husband (Dan Blocker).
But, with considerably more sophistication than that, the story takes the more interesting tack of character development. Alan, who might appear to be sitting pretty, woman at his beck and call, a glorious modern apartment, cocktails on tap, is brought up sharply by his brother’s delight at such a shallow life. Alan gets to play Hollywood honcho with Peggy while Connie delivers an ultimatum that threatens to bring Frank to his senses though, naturally, he believes it’s all hooey.
The fraternal business is well done, instead of the normal rivalry genuine affection and the older sibling offering guidance, though primarily in how to get drunk and get off with women rather than anything that might otherwise stand him in good stead. Though you might argue that being shown how to dress, and how converse with women, and organise a fun party might be as much education as a young gentleman in the Big Apple required.

Playwright Neil Simon, the toast of Broadway at this stage, exhibited such a keen sense of structure that the story never sagged. Any time that appeared a remote possibility, instead of a stranger coming in a la Raymond Chandler with a gun, it’s Harry stomping all over the place. There are some good catchphrases, genuinely funny moments, and some great lines, the best, I have to confess, from Peggy who bemoans the fact that she was stranded in a hotel room with Alan at a ski resort by all the snow outside. Redeeming factor: her homely kind of dumb serves narrative purpose, making the otherwise unbearably charming Alan come across as a heel.
This is quite a different Sinatra, like he’s channeling his record persona, none of the anguish, dramatic intensity or Rat Pack bonhomie he brought to other pictures. Often you hear of actors just playing the same character or a variation thereof, but this ain’t a Sinatra persona I’m familiar with and brings verve to the whole shebang.
Lee J. Cobb (Coogan’s Bluff, 1968) gives in to overacting. You can see how that loud style might work on the stage, but it’s less effective here. Jill St John (Tony Rome, 1967) is very good as the uncertain beauty, who could be incredibly seductive if only she could work out how, and not quite a victim either, and still managing vulnerability. Barbara Rush (Robin and the 7 Hoods, 1964) is wasted, though. Set up as a modern woman, she collapses at the first sniff of marriage, though framing her eyes in a mask of light in a taxi cab is about the only compositional mark of any note.
Quite what possessed director Bud Yorkin (Divorce American Style, 1967) to stick in the title song in the middle of the picture is anybody’s guess. Norman Lear (Divorce American Style) wrote the script but you can hardly go wrong with a Neil Simon template.
End up: it’s mostly about family and people coming to terms with themselves and each other.