一天到晚做着千奇百怪的梦的阿寅，又在想象自己成了天外来客。梦醒过后，刚刚回家，就和人打起架来，气得刚出院的叔叔差点犯了病。阿寅一气之下又离开家，路上在一个小村子落了脚，结识了因失恋正在痛苦中的小伙子。小伙子听从了阿寅的规劝，并来到东京阿寅家散心。在欣赏歌舞剧时，他们被红奈奈子的精湛演技所倾倒。阿寅对奈奈子产生了爱慕之情，但是，奈奈子因为热爱自己的事业，她把舞台看得比什么都重要。她向自己的男友哭诉心中的矛盾，做出痛苦的选择。但是，他们十年的恋情最终战胜了一切，带着眷恋和遗憾，奈奈子向她钟爱的舞台告别了。

Tora-san befriends the descendant of a feudal lord. The man asks Tora to locate his deceased son's wife who resides somewhere in Tokyo.

When Tora-san's infatuation with his nephew's school teacher causes family turmoil, he leaves on his travels again. When he returns, he falls in love with the teacher's mother.

Tora-san arrives in Shibamata on Mitsuo's first day of school only to find that on his account, Mitsuo was embarrassed. After a fight with his family, he goes to a bar to drink, then brings home a surly old man with a sad story, whose identity will surprise everyone. Later, Tora meets Botan, a geisha.

被譽為《男人之苦》系列中的顛峰之作。淺丘瑠璃子飾演的酒吧歌女莉莉繼第11集《寅次郎毋忘我》後第二度登場。寅次郎與離婚後的莉莉重遇，兩人今次感情突飛猛進，還經常手拖手逛街。正當各人以為寅和莉莉天生一對，慫恿他們共諧連理之際，寅卻狠狠地拒絕了這頭婚事，因為他相信：「莉莉是一隻季候鳥──受傷了回家休息，醫好了便展翅翱翔，留不低停不下──像我一樣。」無腳雀仔的鼻祖原來是寅次郎！ Considered the best film in the series, Tora-san Meets the Songstress Again marked the second appearance of Asaoka Ruriko as Lily, the club singer whom Tora encountered in Tora-san's Forget Me Not. Love seems to have blossomed between Tora and the now-divorced Lily, but contrary to the beliefs of friends and family, marriage is not on the minds of the lovers.

《男人之苦》第14集，寅次郎（渥美清飾）未婚產子？背著BB回到了東京柴又老家？正當大家決定替寅把寶寶撫養成人之際，才得知這是寅在路上拾回來的棄嬰！寅不是生父，也當然不盡父職，終日百無聊賴，寶寶的事全拜託嬸嬸和妹妹阿櫻……直至美女護士京子（十朱幸代飾）的出現，他才積極表現父愛，還打算參加京子的工餘合唱團，以親近對方。誰知寅就在這兒遇上情敵！那滿面鬍鬚的窮光蛋指揮，原來才是京子的最愛！ The fourteenth instalment in the Tora-san series. Tora-san has an illegitimate child? To everyone is surprise, he brought a child back to Shibamata. When everyone in his family decides to raise the child as a family member, they find that he was only an abandoned child that Tora-san found on the street! At first, Tora-san has no interest in taking care of the child and he lets his auntie and sister, Sakura, to do the job instead... until he meets the beautiful nurse Kyoko (Toake Yukiyo). He tries all the ways he could, including taking good care of the child, in order to get her attention. However, a bearded poor conductor in Kyoko is choir stands in the way.