Directed by Bud Yorkin, who co-produced this slightly above average light comedy with Norman Lear, who wrote the screenplay adapting a play by Neil Simon, who earned his first motion picture screen credit, it stars 47 year old Frank Sinatra playing a 39 year old older brother to a 21 year old character, played by Tony Bill, and the son of Lee J. Cobb's (though Cobb himself was only 51 at the time) and Molly Picon's (65 at the time) characters, who'd been married for 43 years.
If you can get past all these improbable numbers (and aren't offended by its shallow female, and other stereotypical characterizations), it's actually (still) a pretty entertaining film today. Barbara Rush, Jill St. John, TV Bonanza's Dan Blocker, and Phyllis McGuire round out the primary cast; Dean Martin, Mary Grace Canfield who plays a woman hypnotized into thinking that Sinatra is JFK (an "inside" joke), and Grady Sutton (who can be glimpsed while Sinatra sings the film's title song) are among those who also appear uncredited.
Sinatra plays Alan Baker, a playboy whose refuses to "grow up" and get married, per his father Harry's (Cobb) wishes. Harry blames his wife Sophie (Picon) for being too soft on Alan as a child, hence their "boy's" situation. Both are pleased that Alan's (much) younger brother Buddy (Bill), who still lives at home with them, is more responsible. Of course Buddy's had enough of being treated like a child, and leaves their suburban home to live with Alan in his extravagant bachelor pad in New York (how he affords it is a loose end until the film's end), though only about an hour's drive away, on his 21st birthday. Both sons work in their father's decorative artificial fruit business, Alan as a salesman and Buddy in design (?).
Once Buddy lives with Alan, and with his older brother's encouragement (at least initially), he undergoes a transformation into a younger version of Alan. Buddy learns by example, having seen Alan successfully juggle an attractive air-headed wannabe actress who lives in his building, Peggy John (St. John), a beautiful singer named Connie (Rush) who's conveniently on tour a lot of the time, and even a would-be, though married, client of their father's company Mrs. Eckman (McGuire), a buyer for Neiman Marcus, whose husband's discovery of Alan's swinging sales technique finally gets him in trouble with Mr. Eckman (Blocker), and fired by Harry. Naturally, Buddy's "corruption" is upsetting to their parents as well.
Not only are the characterizations humorous, for example Cobb's Harry is evidently a self-made immigrant who loudly calls his son a 'bum' (though Martin, in a cameo, is the film's only real bum) and Picon plays a long-suffering "Jewish" mother, but the tried and true (silent film) technique of never knowing who's on the other side of Alan's apartment door when the doorbell (or the phone) rings is effectively utilized with comic results. Rush plays a woman whose biological clock is ticking such that she's hoping Alan will settle down with her after only six months of dating. John plays a bubble- headed neighbor who helps Buddy begin his "fling". The film's final third is not as good as the first two thirds, and it does end rather predictably - with Alan seeing the error of his ways through Buddy and deciding to marry Connie. However, that doesn't keep it from being a good ride while it lasts.
The film's Color Art Direction-Set Decoration was nominated for an Academy Award.
If you can get past all these improbable numbers (and aren't offended by its shallow female, and other stereotypical characterizations), it's actually (still) a pretty entertaining film today. Barbara Rush, Jill St. John, TV Bonanza's Dan Blocker, and Phyllis McGuire round out the primary cast; Dean Martin, Mary Grace Canfield who plays a woman hypnotized into thinking that Sinatra is JFK (an "inside" joke), and Grady Sutton (who can be glimpsed while Sinatra sings the film's title song) are among those who also appear uncredited.
Sinatra plays Alan Baker, a playboy whose refuses to "grow up" and get married, per his father Harry's (Cobb) wishes. Harry blames his wife Sophie (Picon) for being too soft on Alan as a child, hence their "boy's" situation. Both are pleased that Alan's (much) younger brother Buddy (Bill), who still lives at home with them, is more responsible. Of course Buddy's had enough of being treated like a child, and leaves their suburban home to live with Alan in his extravagant bachelor pad in New York (how he affords it is a loose end until the film's end), though only about an hour's drive away, on his 21st birthday. Both sons work in their father's decorative artificial fruit business, Alan as a salesman and Buddy in design (?).
Once Buddy lives with Alan, and with his older brother's encouragement (at least initially), he undergoes a transformation into a younger version of Alan. Buddy learns by example, having seen Alan successfully juggle an attractive air-headed wannabe actress who lives in his building, Peggy John (St. John), a beautiful singer named Connie (Rush) who's conveniently on tour a lot of the time, and even a would-be, though married, client of their father's company Mrs. Eckman (McGuire), a buyer for Neiman Marcus, whose husband's discovery of Alan's swinging sales technique finally gets him in trouble with Mr. Eckman (Blocker), and fired by Harry. Naturally, Buddy's "corruption" is upsetting to their parents as well.
Not only are the characterizations humorous, for example Cobb's Harry is evidently a self-made immigrant who loudly calls his son a 'bum' (though Martin, in a cameo, is the film's only real bum) and Picon plays a long-suffering "Jewish" mother, but the tried and true (silent film) technique of never knowing who's on the other side of Alan's apartment door when the doorbell (or the phone) rings is effectively utilized with comic results. Rush plays a woman whose biological clock is ticking such that she's hoping Alan will settle down with her after only six months of dating. John plays a bubble- headed neighbor who helps Buddy begin his "fling". The film's final third is not as good as the first two thirds, and it does end rather predictably - with Alan seeing the error of his ways through Buddy and deciding to marry Connie. However, that doesn't keep it from being a good ride while it lasts.
The film's Color Art Direction-Set Decoration was nominated for an Academy Award.