On the road again, Torajiro meets a kindred spirit in Lily, a lounge singer.

Tora-San returns to Shibamata just before his family leaves on a trip for Kyushu. Later, he encounters an old school chum and begins to have feeling for his artist sister.

After Torajiro's latest attempt to find a bride goes awry, he starts traveling again and runs into Utako (last seen in Tora-san's Dear Old Home), now a widow.

Kuruma Torajiro is discovered looking around Kyoto for someone special to him.

Torajiro becomes homesick during his travels after watching a television report about his hometown and meeting a young woman that reminds him of his sister Sakura. Meanwhile, a new tenant moves into Toraya restaurant.

寅次郎收到莉莉從沖繩寄來的信，原來她在夜總會唱歌時暈倒入院，還說：「臨死前，很想見寅一面」。寅馬上趕到沖繩照顧莉莉，縱然闊別了五年，兩人的感情有增無減，莉莉休養期間，寅更隨傳隨到，旁人都以為他們是夫妻……淺丘瑠璃子演的莉莉第三度登場，叫寅再三考慮「結婚問題」。山田自言「這是我最愛的作品之一」，渥美清去世後，山田在《男人之苦》系列中只選了本片(加插新片段)推出特別版來紀念這位一代巨星。
Upon receipt of a letter from Lily telling Tora that she would like to see him before she dies, Tora rushes to Okinawa, where Lily has fainted during one of her performances. Although five years has passed since they parted, the former couple continues to care about each other, and Tora nurses Lily to health. The personal favourite of Yamada Yoji , Tora-san's Tropical Fever was the only film re-released (with added scenes) by the director to commemorate Atsumi Kiyoshi after the superstar's death.

Tora-san returns to his family's home to attend an elementary school class reunion. After he embarrasses himself by getting drunk and insulting all his ex-classmates, he resumes his travels. In Kyushu he meets an outspoken 18-year-old girl who becomes enamored of Tora-san and follows him around. One of Tora-san's old friends is terminally ill and makes Tora-san promise him to marry his wife once he is gone.

When his travels bring him to Osaka, Tora-san falls in love with a local geisha. He helps her to track down her estranged brother, and informs his family that he plans to marry her. His plans are foiled when the geisha informs Tora-san that she is engaged.

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.

The story is set in 1970 during the time of the first EXPO in Japan. The film’s main figure is a miner who suddenly becomes unemployed because the mine he worked in was shut down. He decides to resettle with his whole family to Hokkaido in northern Japan and start a new life as a farmer.

After an encounter with a dying yakuza's son and at his sister Sakura's urging, Torajiro attempts to change his vagrant lifestyle and become an honest worker with a steady job.