Songs tend to bear the collective sentiments and the memories of the era when they were created. Some of them represent the zeitgeist among which they came, some the reflection on certain political or cultural events, while some the expression of the subtle, personal feelings of the artists themselves. But the meaning of a song is not solidified after its creation: presented in different times and contexts, a song may represent different collective memories and identification. The study explores the covering and adaptation of classic Mandarin and Taiwanese pop songs in Taiwan since 1990s. Various attempts they may have behind their music, the pop singers and singer-songwriters during that period of time, through their act of covering and adaptation of the classics, called for the collective memories and identification that once embedded in the classics. The study scrutinizes some of the pop songs at that time that were the cover or adaptation of certain classics, divides them into several categories, and analyzes the meanings they may have in cultural contexts. In early 1990s, several years after the lifting of Martial Law, a number of Taiwanese singer-songwriters began writing songs known as new mother-language music. Bathed in an atmosphere more liberal than the past few decades, they began writing new pieces in their native languages, while recomposing and performing certain Taiwanese classics that were written during the Martial Law era. From then on, a series of interaction between the contemporary pop music and the classics began flourishing. Among them were the adaptation of the Mandarin or Taiwanese classics, sampling in hip-hop music, self-collection of the popular pieces, and the collage of elements seen in the classics. These acts called for the connection of the classics, as well as the cultural meanings once embedded in those classics, while producing new interpretations in the songwriters' own time. These acts thus created a space, larger than one by simply covering, for various elements to dialogue in the music. Two different eras, styles, or even more, collided one another through the adaptation of the lyrics, melody, or the re-composition of the classics. While the classics themselves came in presence together with their zeitgeist, these adaptations also created new collective memories and identifications, forming multi-layers of flowing sentiments across the times. The collective memories and identification, once thought to be bound with the songs themselves, were given new meanings through the covering and adaptation of the classics in contemporary pop music in Taiwan. The initial collective memories and the identification, once thought to be bound with the songs themselves and the era when the songs were born, were given new meanings through the acts above. The classics, at the same time, were given new representing forms, loosening their bond with the political and cultural context in which they were born. While the collective memories and the identification embedded in the classics were still called into presence with these acts, the contemporary social issues were also intertwined in the music, giving the classics new interpretations. All together, the meanings of the classics were made more abundant in contemporary pop music