Uvama urubugal in Tamil are used to explain a particular context by citing another equivalent context. This is referred to as “Uvamaiyani” in Tamil Grammar rules as stated in Tholkappiam. The is called as simile in English. Similes bring out many beautiful poetic contexts. Automatic extraction of such similes can help to build better Natural Language Generation applications such as, story generation systems and lyric suggestion systems. This paper attempts to automatically extract the uvama urubugal from Tamil Sangam Literatures. Natrinai and Mullai Pattu have been used for the analysis. There are 12 uvama urupugal in Tamil as per Nanool and this paper has attempted to analyze the usage of these 12 uvama urubugal in Sangam Literatures and compares their usage distribution in the Tamil Film songs data set comprising of 4215 songs. It was found that only two uvama urubugal were used in the current-day Tamil Film songs. This comparison was done to reveal the diminishing usage of these beautiful uvama urubugal by the current generation and the urge to use them again.